- Inhibitory Evaluation and Molecular Docking Analysis of Benzenesulfonamides on Carbonic Anhydrase II
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Abstract: Sulfonamides is an important class of compounds, which can be used as carbonic anhydrase inhibitors. Nine different benzenesulfonamide compounds were synthesized, and their inhibitory effects on carbonic anhydrase II were studied by esterase method and molecular docking. The results showed that compounds (IId)–(IIg) with nitro and acetamide groups on the benzene ring exhibited excellent carbonic anhydrase II inhibitory activities. Molecular docking showed that compared with the control inhibitor acetazolamide, the compounds (IId)–(IIg) docked at the carbonic anhydrase II active site and showed higher binding energy and stronger binding ability. The physical and chemical properties of all compounds were studied by Molinspiration, which showed outstanding drug-like properties and ADME properties. Cytotoxicity assay results showed that compounds (IIe) and (IIf) were almost non-toxic to HepG2 and RAW264.7 cells. In conclusion, the compounds (IIe) and (IIf) have a certain application prospect as new inhibitors of carbonic anhydrase II.
- Zhang,Wei,Liu,Wu,Xuan
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p. 261 - 269
(2021/03/23)
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- Convenient synthesis of spiroindolenines from tryptamine-derived isocyanides and organic azides by cobalt catalysis in pure water
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A Co-catalyzed coupling of 3-(2-isocyanoethyl)indoles with organic azides in pure water for accessing spiroindolenine derivatives was developed. This strategy features mild reaction conditions, high atom-economy, excellent yields, wide substrate scopes, and broad functional group tolerance. The products were obtained simply by sequential operation involving extraction, concentration, precipitation, and filtration, without tedious column chromatography. More importantly, the aqueous catalytic system could be recycled at least ten times without reducing the catalytic activity. The strategy provides a green and efficient method for the construction of spiroindolenine derivatives.
- Jiang, Shuai,Cao, Wen-Bin,Li, Hai-Yan,Xu, Xiao-Ping,Ji, Shun-Jun
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supporting information
p. 2619 - 2623
(2021/04/21)
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- Controlling Selectivity in the Synthesis of Z-α,β-Unsaturated Amidines by Tuning the N-Sulfonyl Group in a Rhodium(II) Catalyzed 1,2-H Shift
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N2-Sulfonyl-α-diazo amidines can be synthesized by the reaction of electron rich alkynyl amines with electron poor sulfonyl azides through 1,3-dipolar cycloaddition that proceeds with perfect regioselectivity. In the presence of rhodium(II) carboxylate catalysts, denitrogenation occurs to give the corresponding metallocarbene but there are then two competing processes: 1,2–H shift and O-transfer from the sulfonyl group to the metallocarbene center. The outcome can be controlled using an electron poor nitrobenzenesulfonyl group and large carboxylate rhodium ligands to select for 1,2–H shift, forming α,β-unsaturated amidines in high yield and with excellent Z-selectivity.
- Boyer, Alistair,Martin, Matthew L.
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supporting information
p. 5857 - 5861
(2021/11/27)
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- One-pot synthesis of sulfonyl-1H-1,2,3-triazolyl-thiomorpholine 1,1-dioxide derivatives and evaluation of their biological activity
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A one-pot procedure for the synthesis of novel 1,2,3-triazole derivatives (5a–5l) in good yields (63 to 77%) using different sulfonic acids and 4-(prop-2-yn-1-yl)thiomorpholine 1,1-dioxide through the in situ generated sulfonyl azides was developed. The structures of the newly synthesized compounds were confirmed by 1H NMR, 13C NMR, mass spectrometry, and elemental analysis. The newly synthesized compounds were screened for in?vitro antibacterial activity and free radical scavenging activity in terms of hydrogen donating or radical scavenging ability by the DPPH method. Among all, the compound N-(4-((4-((1,1-dioxidothiomorpholino) methyl)-1H-1,2,3-triazol-1-yl)sulfonyl)phenyl) acetamide (5l) was found to exhibit potent activity as compared to the standard drugs.
- Sreerama, Rakesh,Narasimha Swamy,Ravinder,Vasudeva Reddy,Narsimha, Sirassu
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p. 455 - 460
(2020/12/17)
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- A Base-Controlled Reaction of 2-Cyanoacetamidines (3,3-Diaminoacrylonitriles) with Sulfonyl Azides as a Route to Nonaromatic 4-Methylene-1,2,3-triazole-5-imines
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Reactions of 2-cyanoacetamidines with sulfonyl azides were shown to take place via two different pathways to form a mixture of 1-substituted 5-amino-1,2,3-triazoles 3 and novel 4-methylene-1H-1,2,3-triazole-5(4H)-imine derivatives 4–14. In the absence of
- Silaichev, Pavel S.,Beryozkina, Tetyana V.,Novikov, Mikhail S.,Dehaen, Wim,Bakulev, Vasiliy A.
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p. 3688 - 3698
(2020/06/09)
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- Rh(III)-Catalyzed C(8)-H Activation of Quinoline N-Oxides: Regioselective C-Br and C-N Bond Formation
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A highly efficient and regioselective Rh(III)-catalyzed protocol for C8-bromination and amidation of quinoline N-oxide was developed. The transformation was found to be successful up to gram scale with excellent functional group tolerance and wide substrate scope. The mechanistic study revealed five-membered rhodacycle with quinoline N-oxide as a key intermediate for regioselective C8-functionalization. In addition, NFSI (N-fluorobis(phenylsulfonyl)-imide) was explored as an amidating reagent for C8-amidation of quinoline N-oxide for the first time.
- Dhiman, Ankit Kumar,Gupta, Shiv Shankar,Sharma, Ritika,Kumar, Rakesh,Sharma, Upendra
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p. 12871 - 12880
(2019/11/02)
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- Regioselective C-H Amidation of (Alkyl)arenes by Iron(II) Catalysis
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A nondirected amidation reaction of aromatic C-H bond was developed under iron(II) catalysis, using sulfonyl azides as the nitrogen source. The reaction displayed a broad substrate scope and good regioselectivities in the aspects of aromatic ring vs alkyl
- Ding, Yao,Zhang, Shen-Yuan,Chen, Yu-Chen,Fan, Shuai-Xin,Tian, Jie-Sheng,Loh, Teck-Peng
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supporting information
p. 2736 - 2739
(2019/04/16)
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- Visible-Light-Mediated Sulfonylimination of Tertiary Amines with Sulfonylazides Involving Csp3-Csp3 Bond Cleavage
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Visible-light-induced cross-coupling of arylsulfonyl azides with tertiaryamines in the presence of Eosin Y at room temperature has been achieved. This transformation features alkyl C-C bond cleavage and provides a green approach to N-sulfonylamidines under mild conditions.
- Gui, Jiao,Xie, Haisheng,Jiang, Huanfeng,Zeng, Wei
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supporting information
p. 2804 - 2807
(2019/04/30)
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- Palladium(0)-Catalyzed Carbonylative Synthesis of N-Acylsulfonamides via Regioselective Acylation
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N-Acylsulfonamides represent an important bioisostere of carboxylic acids that allow for greater molecular elaboration and enhanced hydrogen bonding capabilities. Herein, we present a mild and convenient palladium(0)-catalyzed synthesis of N-acylsulfonamides via the carbonylative coupling of sulfonyl azides and electron-rich heterocycles. The reaction proceeds via in situ generation of a sulfonyl isocyanate followed by regioselective acylation of an indole or pyrrole nucleophile. This approach has been used to synthesize 34 indole- and pyrrole-substituted N-acylsulfonamides in yields of up to 95%. Importantly, this process is ligand-free and compatible with an ex situ solid CO source and requires only slightly elevated temperatures, making it a highly attractive method for the preparation of this important class of compounds. This study further investigated the possibility of labeling N-acylsulfonamides with carbon-11 to facilitate biological evaluation and in vivo studies with positron emission tomography.
- Schembri, Luke S.,Eriksson, Jonas,Odell, Luke R.
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p. 6970 - 6981
(2019/06/14)
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- C-H alkenylation/cyclization and sulfamidation of 2-phenylisatogens using: N -oxide as a directing group
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The first example of transition-metal-catalyzed C-H activations of 2-phenylisatogens with alkynes and sulfonyl azides has been developed using N-oxide as the directing group. Ru(ii)-Catalyzed C-H alkenylation/cyclization and Ir(iii)-catalyzed direct C-H sulfamidation proceeded with good yields and excellent functional group tolerance. Importantly, these two transformations provided straightforward routes for the synthesis of indol-3-one derivatives and sulfamidated 2-phenylisatogens respectively, which might be of considerable bioactivities.
- Guo, Lingmei,Tang, Baolan,Nie, Ruifang,Liu, Yanzhao,Lv, Shan,Wang, Huijing,Guo, Li,Hai, Li,Wu, Yong
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supporting information
p. 10623 - 10626
(2019/09/06)
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- Ru(II)-catalyzed α-sulfonamidation of cyclic β-ketoesters with sulfonyl azides
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α-Sulfonamidation of β-ketoesters with sulfonyl azide has been developed for the first time using a catalytic amount of Ru(II) complex to produce the 1-oxo-2-(sulfonamido)-2,3-dihydro-1H-indene-2-carboxylate and 1-oxo-2-(sulfonamido)-1,2,3,4-tetrahydronaphthalene-2-carboxylate derivatives in good yields. This method also works well with α-iodotetralones to afford the N-(1,4-dioxo-1,4-dihydronaphthalen-2-yl)sulphonamide derivatives under similar conditions.
- Rao, M.V. Krishna,Reddy, K. Nagarjuna,Sridhar,Reddy, B.V. Subba
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supporting information
(2019/09/16)
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- Water/Alkali-Catalyzed Reactions of Azides with 2-Cyanothioacetamides. Eco-Friendly Synthesis of Monocyclic and Bicyclic 1,2,3-Thiadiazole-4-carbimidamides and 5-Amino-1,2,3-triazole-4-carbothioamides
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The reactions of thioamides with azides in water were studied. It was reliably shown that the reaction of 2-cyanothioacetamides 1 with various types of azides 2 in water in the presence of alkali presents an efficient, general, one-step, atom-economic, and eco-friendly method for the synthesis of 1,2,3-thiadiazol-4-carbimidamides 5 and 1,2,3-triazole-4-carbothioamides 4. This method can be extended to the one-pot reaction of sulfonyl chlorides and 6-chloropyrimidines 2′o with sodium azide, leading to final products in higher yields, that is, avoiding the isolation of unsafe sulfonyl azides. The method was furthermore applied to the reaction of N,N′-bis-(2-cyanothiocarbonyl)pyrazine 1h with sulfonyl azides to afford bicyclic 1,2,3-thiadiazoles 8 and 1,2,3-triazoles 9 connected via a 1,1′-piperazinyl linker. 2-Cyanothioacetamides 1 were also shown to react with aromatic azides in water in the presence of alkali to afford 1-aryl-5-amino-1,2,3-triazole-4-carbothioamides 11. In contrast to aromatic azides and similarly to sulfonyl azides, 6-azidopyrimidine-2,4-diones 2o-q react with cyanothioacetamides to form N-pyrimidin-6-yl-5-dialkylamino-1,2,3-thiadiazole-4-N-l-carbimidamides 12. A mechanism was proposed to rationalize the role of water in changing the reactivity of azides toward 2-cyanothioacetamides.
- Filimonov, Valeriy O.,Dianova, Lidia N.,Beryozkina, Tetyana V.,Mazur, Dmitrii,Beliaev, Nikolai A.,Volkova, Natalia N.,Ilkin, Vladimir G.,Dehaen, Wim,Lebedev, Albert T.,Bakulev, Vasiliy A.
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p. 13430 - 13446
(2019/10/16)
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- Nitroacenaphthene as a New Photocatalyst for the Synthesis of Sulfonyl Amidines
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A small molecule, namely nitroacenaphthene, is reported for the first time as a recyclable visible-light photocatalyst for the construction of the C=N bond from sulfonyl azides and amines. This scalable, site-selective protocol provides a convenient way to access various sulfonyl amidines under mild conditions. Two reaction pathways are proposed, according to different transformation patterns.
- Chen, Ming,Jian, Yong,Xia, Wujiong,Yang, Chao
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p. 4425 - 4433
(2019/11/21)
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- Tert -Butyl nitrite mediated nitrogen transfer reactions: Synthesis of benzotriazoles and azides at room temperature
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A conversion of o-phenylenediamines into benzotriazoles was achieved at room temperature using tert-butyl nitrite. The optimized conditions are also well suited for the transformation of sulfonyl and acyl hydrazines into corresponding azides. This protocol does not require any catalyst or acidic medium. The desired products were obtained in excellent yields in a short span of time.
- Azeez, Sadaf,Chaudhary, Priyanka,Sureshbabu, Popuri,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
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supporting information
p. 6902 - 6907
(2018/10/02)
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- Palladium-Catalyzed One-Pot Synthesis of N -Sulfonyl, N -Phosphoryl, and N -Acyl Guanidines
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An efficient palladium-catalyzed cascade reaction of azides with isonitrile and amines is presented; it offers an alternative facile approach toward N -sulfonyl-, N -phosphoryl-, and N -acyl-functionalized guanidines in excellent yield. These series of substituted guanidines exhibit potential biological and pharmacological activities. In addition, the less reactive intermediate benzoyl carbodiimide could be isolated by silica gel column flash chromatography in moderate yield.
- Qiao, Guanyu,Zhang, Zhen,Huang, Baoliang,Zhu, Liu,Xiao, Fan,Zhang, Zhenhua
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supporting information
p. 330 - 340
(2018/01/12)
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- Iridium(III)-Catalyzed Selective and Mild C-H Amidation of Cyclic N-Sulfonyl Ketimines with Organic Azides
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A general protocol for iridium catalyzed direct C?H amidation of cyclic N-sulfonyl ketimines using sulfonyl, acyl and aryl azides as nitrogen source is reported herein. The reaction takes place at room temperature with acyl and aryl azides, while an elevated temperature needed with sulfonyl azides to furnish aminated sultams in excellent yields with complete chemo and regioselectivity, thus providing a robust and environmentally benign process to the synthesis of aminosultams. (Figure presented.).
- Maraswami, Manikantha,Chen, Gang,Loh, Teck-Peng
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supporting information
p. 416 - 421
(2017/11/13)
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- Polycyclic Indoline-Benzodiazepines through Electrophilic Additions of α-Imino Carbenes to Tr?ger Bases
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Polycyclic indoline-benzodiazepines can be accessed through the intermolecular reaction of Tr?ger bases with N-sulfonyl-1,2,3-triazoles. Under RhII catalysis, α-imino carbenes are generated and a subsequent cascade of [1,2]-Stevens, Friedel–Cra
- Bosmani, Alessandro,Guarnieri-Ibá?ez, Alejandro,Goudedranche, Sébastien,Besnard, Céline,Lacour, Jér?me
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supporting information
p. 7151 - 7155
(2018/05/29)
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- Iridium-Catalyzed Direct Regioselective C4-Amidation of Indoles under Mild Conditions
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An efficient Ir-catalyzed amidation of indoles with sulfonyl azides is disclosed, affording diverse C4-amidated indoles exclusively under mild conditions. In this protocol, a variety of indoles with commonly occurring functional groups such as formyl, acetyl, carboxyl, amide, and ester at the C3 position are well tolerated.
- Chen, Shuyou,Feng, Boya,Zheng, Xuesong,Yin, Jiangliang,Yang, Shiping,You, Jingsong
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supporting information
p. 2502 - 2505
(2017/05/24)
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- A Direct Access to 7-Aminoindoles via Iridium-Catalyzed Mild C-H Amidation of N-Pivaloylindoles with Organic Azides
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Ir(III)-catalyzed regioselective direct C-7 amidation of indoles in reaction with organic azides has been developed. While its efficiency was varied by the choice of N-directing groups, N-pivaloylindoles were most effective in undergoing the desired amidation at room temperature over a broad range of substrates. The reaction was scalable, and deprotection of the chelation group was also facile.
- Kim, Youyoung,Park, Juhyeon,Chang, Sukbok
-
supporting information
p. 1892 - 1895
(2016/05/19)
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- Product-Derived Bimetallic Palladium Complex Catalyzes Direct Carbonylation of Sulfonylazides
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A novel product-derived bimetallic palladium complex catalyzes a sulfonylazide-transfer reaction with the σ-donor/π-acceptor ligand CO, and is advantageous given its broad substrate scope, high efficiency, and mild reaction conditions (atmospheric pressure of CO at room temperature). This methodology provides a new approach to sulfonylureas, which are present in both pharmaceuticals and agrochemicals. The synthesis of Glibenclamide on a gram scale further revealed the practical utility of this procedure. Mechanistically, the generation of a bridged bimetallic palladium species derived from the product sulfonylurea is disclosed as the crucial step for this catalytic cycle.
- Zhao, Jin,Li, Zongyang,Song, Shaole,Wang, Ming-An,Fu, Bin,Zhang, Zhenhua
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supporting information
p. 5545 - 5549
(2016/05/09)
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- A Novel Copper-Catalyzed Preparation of Pyrido[1,2- a ]pyrimidine Derivatives
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A copper-catalyzed reaction of 2-amino-1-(prop-2-yn-1-yl)pyridinium bromide derivatives and aromatic sulfonyl azides has been demonstrated under mild condition.
- Mahdavi, Mohammad,Estabragh, Roxana Fazli,Moghimi, Setareh,Sayahi, Mohammad Hosein,Shafiee, Abbas,Foroumadi, Alireza
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p. 1359 - 1362
(2016/06/01)
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- Synthesis of Sulfonyl Azides via Lewis Base Activation of Sulfonyl Fluorides and Trimethylsilyl Azide
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A protocol for the efficient conversion of sulfonyl fluorides into sulfonyl azides through Lewis base activation is described. The in situ generated sulfonyl azides are efficient diazo-transfer agents, affording diazo compounds and primary azides in excellent yields.
- Barrow, Andrew S.,Moses, John E.
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supporting information
p. 1840 - 1843
(2016/07/16)
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- Transition-metal-free direct amination of simple arenes with sulfonyl azides
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A metal-free green protocol has been developed for amination of simple arenes using arylsulfonyl azides via a nitrene transfer process under solvent free conditions at 130 °C releasing N2 gas as the sole by-product.
- Wang, Lianggui,Borah, Arun Jyoti,Yan, Guobing
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supporting information
p. 1353 - 1355
(2015/03/04)
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- Iridium-Catalyzed Direct C-H Sulfamidation of Aryl Nitrones with Sulfonyl Azides at Room Temperature
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Ir(III)-catalyzed direct C-H sulfamidation of aryl nitrones has been developed to synthesize various sulfamidated nitrones in moderate to excellent yields with excellent regioselectivity and broad functional group tolerance. This transformation could proceed smoothly at room temperature with low catalyst loading in the absence of external oxidants, acids, or bases. Molecular nitrogen was released as the sole byproduct, thus providing an environmentally benign sulfamidation process. And this protocol could efficiently apply to synthesize the substituted benzisoxazoline via one-step transformation from the product.
- Pi, Chao,Cui, Xiuling,Wu, Yangjie
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p. 7333 - 7339
(2015/08/18)
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- Nucleophilic Substitution Reactions of 2,4-Dinitrophenyl X-Substituted-Benzenesulfonates and Y-Substituted-Phenyl 4-Nitrobenzenesulfonates with Azide Ion: Regioselectivity and Reaction Mechanism
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The second-order rate constants for reactions of 2,4-dinitrophenyl X-substituted-benzenesulfonates (4a-4f) and Y-substituted-phenyl-4-nitrobenzenesulfonates (5a-5f) with N3- ion have been measured spectrophotometrically. The reactions of 4a-4f proceed through S-O and C-O bond fission pathways competitively. Fraction of the S-O bond fission decreases rapidly as the substituent X in the benzenesulfonyl moiety changes from an electron-withdrawing group to an electron-donating group. The Hammett plots for reactions of 4a-4f are linear with ρX=1.87 and 0.56 for the S-O and C-O bond fission, respectively. The fact that the substituent X is further away from the reaction site of the C-O bond fission than that of the S-O bond fission is one reason for the smaller ρX value. The nature of the reaction mechanism (i.e., a stepwise mechanism in which expulsion of the leaving group occurs after the rate-determining step) is also responsible for the smaller ρX value obtained from the C-O bond fission. The Bronsted-type plot for the reactions of 5a-5f is linear with βlg=-0.63, which is typical for reactions reported previously to proceed through a concerted mechanism. Effects of substituents X and Y on regioselectivity and reaction mechanism are discussed in detail.
- Moon, Ji-Hyun,Kim, Min-Young,Han, So-Yeop,Um, Ik-Hwan
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p. 1360 - 1365
(2015/07/15)
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- Iridium-catalyzed direct ortho-C-H amidation of benzoic acids with sulfonylazides
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A mild and efficient iridium-catalyzed ortho-C-H amidation with sulfonyl azides by weakly coordinating carboxylic acid was demonstrated, which provided a novel approach to anthranilic acid derivatives.
- Wei, Ming-E,Wang, Lian-Hui,Li, Yu-Dong,Cui, Xiu-Ling
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supporting information
p. 1336 - 1340
(2015/10/28)
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- Preparation of triazoloindoles via tandem copper catalysis and their utility as α-imino rhodium carbene precursors
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3-Sulfonyl[1,2,3]triazolo[4,5-b]indoles were efficiently prepared via a tandem catalysis process involving intramolecular ligand stabilized CuAAC and Cu-catalyzed C-N coupling. The obtained 3-sulfonyl[1,2,3]triazolo[4,5-b]indoles could be utilized as α-im
- Xing, Yanpeng,Sheng, Guorong,Wang, Jing,Lu, Ping,Wang, Yanguang
-
supporting information
p. 1244 - 1247
(2014/03/21)
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- Iridium-catalyzed intermolecular amidation of sp3 C-H bonds: Late-stage functionalization of an unactivated methyl group
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Reported herein is the iridium-catalyzed direct amidation of unactivated sp3 C-H bonds. With sulfonyl and acyl azides as the amino source, the amidation occurs efficiently under mild conditions over a wide range of unactivated methyl groups with high functional group tolerance. This procedure can be successfully applied for the direct introduction of an amino group into complex compounds and thus can serve as a powerful synthetic tool for late-stage C-H functionalization.
- Kang, Taek,Kim, Youngchan,Lee, Donggun,Wang, Zhen,Chang, Sukbok
-
supporting information
p. 4141 - 4144
(2014/04/03)
-
- Access to the aeruginosin serine protease inhibitors through the nucleophilic opening of an oxabicyclo[2.2.1]heptane: Total synthesis of microcin SF608
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Serine proteases play key roles in many biological processes and are associated with several human diseases such as thrombosis or cancer. During the search for selective inhibitors of serine proteases, a family of linear peptides named the aeruginosins was discovered in marine cyanobacteria. We herein report an entry route into the synthetically challenging core fragment of these natural products. Starting from the common oxabicyclic building block 11, we accessed the octahydroindole core of the aeruginosins, exemplified by the total synthesis of microcin SF608 (2). Key to the synthetic strategy is a highly efficient nucleophilic opening of an oxabicyclo[2.2.1]heptane producing the hydroindole motif of microcin SF608. Moreover, during the synthetic efforts we have observed an unusual regioselective epoxide reduction. Detailed experimental studies of this reaction led us to propose a mechanistic rationale involving intramolecular hydrogen atom delivery by a carbamate NH group to control the regioselectivity of the homolytic epoxide cleavage. Expect the unexpected! An entry route to the aeruginosin protease inhibitors is reported and showcased on the total synthesis of microcin SF608 (see scheme). Detailed experimental studies of an unusual regioselective epoxide reduction observed during this synthesis suggests a mechanistic rationale for this transformation involving intramolecular hydrogen atom delivery by a carbamate NH to direct the regioselectivity of the homolytic epoxide cleavage.
- Diethelm, Stefan,Schindler, Corinna S.,Carreira, Erick M.
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supporting information
p. 6071 - 6080
(2014/05/20)
-
- Synthesis of 2-Aryl-2 H-benzotrizoles from azobenzenes and N-sulfonyl azides through sequential rhodium-catalyzed amidation and oxidation in one pot
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An efficient synthetic method of 2-aryl-2H-benzotriazoles from nonprefunctionalized azobenzenes and N-sulfonyl azides via sequential Rh-catalyzed amidation (C-N bond formation) and oxidation (N-N bond formation) with PhI(OAc)2 in one pot is reported.
- Ryu, Taekyu,Min, Jiae,Choi, Wonseok,Jeon, Woo Hyung,Lee, Phil Ho
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supporting information
p. 2810 - 2813
(2014/06/23)
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- One-step synthesis of nitrogen-containing medium-sized rings via α-imino diazo intermediates
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Eight- and 9-membered dioxazocines and dioxazonines are readily synthesized starting from N-sulfonyl-1,2,3-triazoles in a single-step procedure. A perfect regioselectivity and generally good yields (up to 92%) are obtained under dirhodium catalysis using
- Medina, Florian,Besnard, Celine,Lacour, Jerome
-
supporting information
p. 3232 - 3235
(2014/07/08)
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- Rhodium(III)-catalyzed intermolecular amidation with azides via C(sp 3)-H functionalization
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The amidation reactions of 8-methylquinolines with azides catalyzed by a cationic rhodium(III) complex proceed efficiently to give quinolin-8- ylmethanamine derivatives in good yields via C(sp3)-H bond activation under external oxidant-free conditions. A catalytically competent five-membered rhodacycle has been isolated and characterized, revealing a key intermediate in the catalytic cycle.
- Wang, Nuancheng,Li, Renhe,Li, Liubo,Xu, Shansheng,Song, Haibin,Wang, Baiquan
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p. 5379 - 5385
(2014/06/23)
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- Copper-catalyzed three-component synthesis of 3-Aminopyrazoles and 4-iminopyrimidines via β-alkynyl-N-sulfonyl ketenimine intermediates
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3-Aminopyrazoles and 4-iminopyrimidines were efficiently prepared via copper-catalyzed three-component reactions of butadiynes, sulfonylazides, and hydrazides or imidamides. The reactions were regioselectively approached via the formation of a β-alkynyl-N-sulfonyl ketenimine intermediate which represented a new and effective 1,3-dielectrophilic equivalent in organic synthesis.
- Xing, Yanpeng,Cheng, Binyu,Wang, Jing,Lu, Ping,Wang, Yanguang
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supporting information
p. 4814 - 4817
(2015/04/27)
-
- Cu-catalyzed multicomponent polymerization to synthesize a library of poly(N -sulfonylamidines)
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We report a versatile Cu-catalyzed multicomponent polymerization (MCP) technique that enables the synthesis of high-molecular-weight, defect-free poly(N-sulfonylamidines) from monomers of diynes, sulfonyl azides, and diamines. Through a series of optimizations, we discovered that the addition of excess triethylamine and the use of N,N′-dimethylformamide as a solvent are key factors to ensure efficient MCP. Formation of cyclic polyamidines was a side reaction during polymerization, but it was readily controlled by using diynes or diamines with long or rigid moieties. In addition, this polymerization is highly selective for three-component reactions over click reactions. The combination of the above factors enables the synthesis of high-molecular-weight polymers, which was challenging in previous MCPs. All three kinds of monomers (diynes, sulfonyl azides, and diamines) are readily accessible and stable under the reaction conditions, with various monomers undergoing successful polymerization regardless of their steric and electronic properties. Thus, we synthesized various high-molecular-weight, defect-free polyamidines from a broad range of monomers while overcoming the limitations of previous MCPs, such as low conversion and defects in the polymer structures.
- Lee, In-Hwan,Kim, Hyunseok,Choi, Tae-Lim
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supporting information
p. 3760 - 3763
(2013/04/24)
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- Sulfoximine directed intermolecular o-C-H amidation of arenes with sulfonyl azides
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The Ru(II)-catalyzed intermolecular o-C-H amidation of arenes in N-benzoylated sulfoximine with sulfonyl azides is demonstrated. The reaction proceeds with broad substrate scope and tolerates various functional groups. Base hydrolysis of the amidation product provides the anthranilic acid derivatives and methylphenyl sulfoximine (MPS) directing group. This method is successfully employed for the synthesis of HMR 1766.
- Yadav, M. Ramu,Rit, Raja K.,Sahoo, Akhila K.
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supporting information
p. 1638 - 1641
(2013/06/27)
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- Ru(ii)-catalyzed intermolecular ortho-C-H amidation of aromatic ketones with sulfonyl azides
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Ru(ii)-catalyzed intermolecular ortho-C-H amidation of weakly coordinating aromatic ketones with sulfonyl azides is reported. The developed reaction protocol can be extended to various substituted aromatic ketones to afford a wide range of desired C-N bond formation products in good yields.
- Bhanuchandra,Ramu Yadav,Rit, Raja K.,Rao Kuram, Malleswara,Sahoo, Akhila K.
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supporting information
p. 5225 - 5227
(2013/06/27)
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- One-pot synthesis of sulfonamides and sulfonyl azides from thiols using chloramine-T
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A convenient synthesis of sulfonamides and sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols was accomplished by oxidation with chloramine-T (=N-chlorotosylamide=N-chloro-4- methylbenzenesulfonamide), tetrabutylammonium chloride (Bu4NCl), and H2O. The sulfonyl chlorides were then further allowed to react with excess amine or NaN3 in the same pot.
- Maleki, Behrooz,Hemmati, Saba,Tayebee, Reza,Salemi, Sirous,Farokhzad, Yasaman,Baghayeri, Mehdi,Zonoz, Farrokhzad Mohammadi,Akbarzadeh, Elahe,Moradi, Rohollah,Entezari, Azam,Abdi, Mohammad Reza,Ashrafi, Samaneh Sedigh,Taimazi, Fereshteh,Hashemi, Majid
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p. 2147 - 2151
(2013/12/04)
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- Synthesis of N,N′-disulfonylamidines from sulfonamides and alkynes by a two-step, one-pot reaction with nonafluorobutanesulfonyl azide
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Nonafluorobutanesulfonyl azide is an advantageous alternative to triflyl azide for the efficient synthesis of sulfonyl azides from sulfonamides in terms of its higher reactivity, lower cost, and non-hazardous nature. The reagent has proven its utility in a novel synthesis of N,N′-disulfonylamidines from available sulfonamides by a copper-catalyzed two-step, one-pot sequential process with added terminal alkynes. Copyright
- Suarez, Jose Ramon,Kwiczak, Joanna,Grenda, Katarzyna,Jimeno, M. Luisa,Chiara, Jose Luis
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p. 913 - 918
(2013/05/08)
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- Synthesis of β-Glycosyl amides from N-glycosyl dinitrobenzenesulfonamides
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The N-glycosyl-2,4-dinitrobenzenesulfonamides were accessed via benzoyl-protected β-glycosyl azides. The azides were reduced with Adams' catalyst to the corresponding amines. The glycosylamines were sulfonated with 2,4-dinitrobenzenesulfonyl chloride to f
- Gaitonde, Vishwanath,Sucheck, Steven J.
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scheme or table
p. 353 - 370
(2012/07/30)
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- Rhodium-catalyzed regioselective amidation of indoles with sulfonyl azides via C-H bond activation
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Direct C-2 amidation of indoles was reported using sulfonyl azides as the amino source to release N2 as the single byproduct. This reaction exhibits high functional group tolerance and regioselectivity, providing a variety of 2-amino substituted indoles in high to excellent yield. The procedure is robust, reliable, and compatible with water and air.
- Shi, Jingjing,Zhou, Bing,Yang, Yaxi,Li, Yuanchao
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supporting information
p. 8953 - 8955
(2013/01/15)
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- A green, catalyst-free method for the synthesis of sulfonamides and sulfonylazides
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A novel, green method for the efficient synthesis of sulfonamide and sulfonylazide derivatives by the reaction of sulfonyl chlorides with amines or sodium azide under catalyst-free conditions has been developed. The reactions proceed with high yields and excellent selectivities in short reaction times. Copyright Taylor & Francis Group, LLC.
- Jafarpour, Maasoumeh,Rezaeifard, Abdolreza,Golshani, Tayebeh
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experimental part
p. 140 - 148
(2011/04/22)
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- Convenient one-pot synthesis of sulfonamides and sulfonyl azides from thiols using N -chlorosuccinimide
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A convenient synthesis of sulfonamides and sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with N-chlorosuccinimide (NCS), tetrabutylammonium chloride, and water. The sulfonyl chlorides are then further allowed to react with excess amine or sodium azide in the same reaction vessel. Georg Thieme Verlag Stuttgart - New York.
- Veisi, Hojat,Ghorbani-Vaghei, Ramin,Hemmati, Saba,Mahmoodi, Jafar
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experimental part
p. 2315 - 2320
(2011/10/13)
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- Cobalt(II)-catalyzed intermolecular benzylic C-H amination with 2,2,2-trichloroethoxycarbonyl azide (TrocN3)
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2,2,2-Trichloroethoxycarbonyl azide (TrocN3) is an effective nitrene source for cobalt(II)-catalyzed intermolecular nitrene insertion of C-H bonds. Among different metalloporphyrins studied, Co(II)(TPP) was shown to be a competent catalyst for the selective amination of various benzylic C-H bonds under mild conditions without the need of other reagents or additives, forming the desired Trocprotected amines in moderate to high yields with nitrogen gas as the only byproduct.
- Lu, Hongjian,Subbarayan, Velusamy,Tao, Jingran,Zhang, X. Peter
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experimental part
p. 389 - 393
(2010/04/04)
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- METAL PORPHYRIN CATALYZED OLEFIN AZIRIDINATION WITH SULFONYL AZIDES
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Cobalt(II) complex of P1 [Co(P1)], a new porphyrin that was designed on the basis of potential hydrogen bonding interactions in the metal-nitrene intermediate, is a highly active catalyst for olefin aziridination with azides. The [Co(P1)]- based system can be effectively employed for different combinations of aromatic olefins and arysulfonyl azides, synthesizing various sulfonylated aziridines in excellent yields. Besides its mild catalytic conditions, the Co-catalyzed aziridination process enjoys several attributes associated with the relatively low cost of cobalt and widely accessible arylsulfonyl azides. Furthermore, it generates stable dinitrogen as the only by-product.
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Page/Page column 36
(2009/12/27)
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- Convenient one-pot synthesis of sulfonyl azides from sulfonic acids
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We have developed a one-pot process for preparing sulfonyl azides by treating sulfonic acids with trichloroacetonitrile, triphenylphosphine, and sodium azide at room temperature. A wide range of sulfonyl azides was synthesized in excellent yields under mild conditions. Georg Thieme Verlag Stuttgart.
- Kim, Joong-Gon,Doo, Ok Jang
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experimental part
p. 2885 - 2887
(2009/04/21)
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- A highly effective cobalt catalyst for olefin aziridination with azides: Hydrogen bonding guided catalyst design
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[Co(P1)], which was designed on the basis of potential hydrogen-bonding interactions in the metal-nitrene Intermediate, Is a highly active aziridination catalyst with azides. [Co(P1)] can effectively azlridlnate various aromatic olefins with arylsulfonyl azides under mild conditions, forming sulfonylated aziridines in excellent yields. The Co-based system enjoys several attributes associated with the relatively low cost of cobalt and the wide accessibility of arylsulfonyl azides. Furthermore, it generates stable dinitrogen as the only byproduct.
- Ruppel, Joshua V.,Jones, Jess E.,Huff, Chelsea A.,Kamble, Rajesh M.,Chen, Ying,Zhang, X. Peter
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supporting information; experimental part
p. 1995 - 1998
(2009/04/10)
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- Advantages of the Ns group in the reactions of N1-SO 2R inosines with benzylamine and with 15NH3
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The reactivity of N1-alkylsulfonyl- and N1- arylsulfonyl-2′,3′,5′-tri-O-acetylinosine with benzylamine and with 15NH3, regarding the attack on C2, has been shown to be in the order CF3SO2 (Tf) > 2,4-(NO 2)2C6H3SO2 (DNs) ≥ 4-NO2C6H4SO2 (pNs) ≈ C 6F5SO2 (PFBs) > 2-NO2C 6H4SO2 (Ns) ? CH3SO2 (Ms) > 4-CH3C6H4SO2 (Ts) > 2,4,6-(CH3)3C6H2SO2 (Mts). In spite of its intermediate reactivity, the Ns group is the most appropriate, since in this case the formation of by-products is minimised during the ring-opening and ring-closing steps of the process. Another advantage of the Ns group is thus disclosed.
- Terrazas, Montserrat,Ariza, Xavier,Vilarrasa, Jaume
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p. 5127 - 5130
(2007/10/03)
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- N-carboalkoxy-2-nitrobenzenesulfonamides: A practical preparation of N- Boc-, N-Alloc-, and N-Cbz-protected primary amines
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N-Carboalkoxy-2-nitrobenzenesulfonamides, readily prepared by acylation of 2-nitrobenzenesulfonamide (o-NsNH2), can be alkylated by either conventional or Mitsunobu protocols. Since the o-nosyl group can be deprotected under mild conditions, a variety of N-carboalkoxy derivatives of primary amines may be prepared in excellent yields from the corresponding alcohols and/or halides. In addition, allyloxycarbonyl (Alloc), t- butoxycarbonyl (t-Boc), and benzyloxycarbonyl (Cbz) groups can be deprotected in the presence of the o-nosyl group, allowing the resultant N-alkylated 2- nitrobenzenesulfonamides to be used for further preparation of secondary amines.
- Fukuyama, Tohru,Cheung, Mui,Kan, Toshiyuki
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p. 1301 - 1303
(2007/10/03)
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- The rhodium(II)-catalyzed aziridination of olefins with {[(4- nitrophenyl)sulfonyl]imino}phenyl-λ3-iodane
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The aziridination of olefins with {(4- nitrophenylsulfonyl)imino}phenyl-λ3-iodane, NsN=IPh (1c), in the presence of [Rh2(OAc)4] proceeds in yields of up to 85% when the olefin is used in large excess. Under optimized conditions, styrene (4a) is aziridinated with 1 equiv. of NsN=IPh (1c) in 64% yield with 2 mol% of catalyst. The aziridines derived from electron-rich olefins undergo ring-opening under the conditions of the aziridination and afford rearrangement products or pyrrolidines. The aziridination is sterospecific with 1,2-dialkyl- and 1,2-arylalkyl- disubstituted olefins, but nonstereospecific with stilbene. The ρ-value for aziridination of substituted styrenes iS -0.61. No ring-opened products are observed upon aziridination of vinylcyclopropanes. In the presence of chiral Rh(II) catalysts, the aziridination is enantioselective, affording an ee of 73% with cis-β-methylstyrene (4k) and Pirrungs [Rh2{(R)-(-)-bnp}4] catalyst. The experimental results are consistent with a one-step mechanism for transfer of the nitrenoid moiety from the catalyst to the olefin.
- Müller, Paul,Baud, Corine,Jacquier, Yvan
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p. 738 - 750
(2007/10/03)
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- Preparation of nitriles from carboxylic acids: A new, synthetically useful example of the Smiles rearrangement
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Reaction of 2,4-dinitrobenzenesulfonamide with acyl chlorides in the presence of excess triethylamine produces the corresponding nitrile in good to fair yields. Mechanistic studies indicate that the reaction proceeds via a Smiles rearrangement of the initially formed N-(2,4- dinitrobenzenesulfonyl)amide to form the nitrile, 2,4-dinitrophenol and sulfur dioxide.
- Huber, Vincent J.,Bartsch, Richard A.
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p. 9281 - 9288
(2007/10/03)
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