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Trifluoromethylthio-containing tryptamine derivative and preparation thereof, and application in prevention and treatment of plant viruses and pathogenic bacteria
The invention relates to a trifluoromethylthio-containing tryptamine derivative I and a preparation method thereof, and application of the trifluoromethylthio-containing tryptamine derivative I in prevention and treatment of plant viruses and pathogenic bacteria. According to the invention, the trifluoromethylthio-containing tryptamine derivative I shows anti-plant virus activity, wherein the inhibition rate of the derivative containing chlorine atoms in the structure on tobacco mosaic virus (TMV) can reach the level equivalent to that of virazole; and the compound also shows certain anti-plant pathogenic bacterium activity, and has relatively good inhibitory activity on physalospora piricola.
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Paragraph 0051; 0054-0055

(2021/06/26)

Uncovering New Excited State Photochemical Reactivity by Altering the Course of the de Mayo Reaction
An unprecedented and previously unknown photochemical reactivity of 1,3-dicarbonyl compounds is observed with amino-alkenes leading to dihydropyrans. This novel photochemical reactivity changes the established paradigm related to the De Mayo reaction between 1,3-dicarbonyl compounds and alkenes. This new reaction allows convenient access to the Marmycin core in a single step from commercially available reactants. The origin and scope of this new photoreaction is detailed with preliminary photophysical and mechanistic investigations.
Kandappa, Sunil Kumar,Valloli, Lakshmy Kannadi,Jockusch, Steffen,Sivaguru, Jayaraman
supporting information
p. 3677 - 3681
(2021/04/07)

Self-catalyzed phototandem perfluoroalkylation/cyclization of unactivated alkenes: Synthesis of perfluoroalkyl-substituted quinazolinones
A novel visible-light-induced radical tandem trifluoromethylation/cyclization of unactivated alkenes with sodium perfluoroalkanesulfinates (Rf = CF3, C3F7, C4F9, C6F13, C8F17) under air atmosphere has been developed. A range of quinazolinones containing unactivated alkene moiety and sodium perfluoroalkanesulfinates were compatible with this transformation, leading to a variety of perfluoroalkyl-substituted quinazoline alkaloids. Remarkably, the experiment can be carried out without any metal catalyst, strong oxidant, or external photosensitizer.
Sun, Bin,Huang, Panyi,Yan, Zhiyang,Shi, Xiayue,Tang, Xiaoli,Yang, Jin,Jin, Can
supporting information
p. 1026 - 1031
(2021/02/06)

Visible-Light-Induced Radical Difluoromethylation/Cyclization of Unactivated Alkenes: Access to CF2H-Substituted Quinazolinones
A mild and efficient visible-light-induced radical difluoromethylation/cyclization of unactivated alkenes toward the synthesis of substituted quinazolinones with easily accessible difluoromethyltriphenylphosphonium bromide has been developed. The transformation has the advantages of wide functional group compatibility, a broad substrate scope, and operational simplicity. The benign protocol offers a facile access to pharmaceutically valuable difluoromethylated polycyclic quinazolinones.
Chen, Xiaoyu,Liu, Bo,Pei, Congcong,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
supporting information
p. 7787 - 7791
(2021/10/20)

Electrochemical oxidative radical cascade cyclization of olefinic amides and thiophenols towards the synthesis of sulfurated benzoxazines, oxazolines and iminoisobenzofurans
Heterocycles containing N and O are important structures in pharmaceuticals, agrochemicals and functional molecules. The synthesis of these compounds usually requires complex substrates and harsh reaction conditions. Herein, we introduce a mild and efficient electrochemical oxidative strategy to construct benzoxazines, oxazolines and iminoisobenzofurans without the requirement of a transition-metal catalyst and an external oxidant. In a simple undivided cell, various olefinic amides and thiophenols/diselenides react to generate 69 examples of thiolation and selenylation heterocycles in up to 83% yields. Furthermore, this radical cascade reaction provided a facile method for constructing C-S/C-Se and C-O bonds in one step.
Alhumade, Hesham,Hu, Jianguo,Huang, Mingna,Jiang, Jianwei,Lei, Aiwen,Li, Hao,Lu, Fangling,Lu, Lijun,Ouyang, Dandan,Sun, Linghong,Wang, Ke,Xu, Jie
supporting information
p. 7982 - 7986
(2021/11/01)

Photo-triggered self-catalyzed fluoroalkylation/cyclization of unactivated alkenes: Synthesis of quinazolinones containing the CF2R group
A novel photo-triggered self-catalyzed fluoroalkylation/cyclization of quinazolinones containing unactivated alkenes with various fluoroalkyl bromides has been developed. This transformation exhibits excellent substrate generality with respect to both the coupling partners. Of note is that this is the first example describing the Csp3-Br bond homolysis of alkyl bromides via a substrate (quinazolinones) induced energy transfer process. Additionally, the mild conditions, tolerance to a wide range of functional groups and operational simplicity make this protocol practical for the synthesis of fluorine-containing ring-fused quinazolinones. This journal is
Yang, Jin,Sun, Bin,Ding, Hao,Huang, Pan-Yi,Tang, Xiao-Li,Shi, Rong-Cheng,Yan, Zhi-Yang,Yu, Chuan-Ming,Jin, Can
supporting information
p. 575 - 581
(2021/01/28)

Photo-Triggered Self-Induced Homolytic Dechlorinative Sulfonylation/Cyclization of Unactivated Alkenes: Synthesis of Quinazolinones Containing a Sulfonyl Group
A self-photocatalyzed sulfonylation/cyclization of quinazolinones containing unactivated alkenes with various sulfonyl chlorides was developed. The protocol provides access to sulfonyl radicals via energy transfer from the quinazolinone skeleton to the sulfonyl chloride. Notably, the transformations proceeded without any external photocatalysts, additives, or oxidants, providing an alternative method for fabricating sulfonylated compounds.
Ding, Hao,Huang, Pan-Yi,Jin, Can,Shen, Run-Pu,Sun, Bin,Tian, Hai-Xia,Wu, Chun-Lei
supporting information

(2021/12/22)

Palladium-Catalyzed Carbamoyl-Carbamoylation/ Carboxylation/Thioesterification of Alkene-Tethered Carbamoyl Chlorides Using Mo(CO)6 as the Carbonyl Source
We reported a palladium-catalyzed carbamoyl-carbamoylation/carboxylation/thioesterification of alkene-tethered carbamoyl chlorides using Mo(CO)6 as the carbonyl source. The reactions were typically performed with good functional group compatibility and tolerated different nucleophiles (amines, alcohols, phenols, thiols and water), which provided a new access to amidated/esterificated/thioesterificated/carboxylated oxindoles or lactams bearing an all-carbon quaternary stereocenter under CO gas-free conditions. Furthermore, natural product mutation and divergent late-stage derivatization are the important practical features.
Chen, Chen,Ding, Jie,Huang, Yujie,Liu, Liying,Zhu, Bolin
supporting information

(2022/01/04)

PHOTOCHEMICAL SYNTHESIS OF MARMYCIN ANALOGUES THROUGH A NEW PHOTOCHEMICAL REACTION INVOLVING CARBONYL COMPOUNDS
Photochemical reactivity of carbonyl compounds leading to the synthesis of the Marmycin core is described. The photochemical reactivity involves an excited state reaction that provides convenient access to bicyclic compounds. The disclosed reactivity is a
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Paragraph 00112-00115

(2021/11/13)

Photocatalyzed Intramolecular [2+2] Cycloaddition of N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides
N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides are converted into natural product inspired scaffolds via iridium photocatalyzed intramolecular [2+2] photocycloaddition. The protocol has a broad substrate scope, whilst operating under mild reaction conditions. Tethering four components forming a trisubstituted cyclobutane core builds rapidly high molecular complexity. Our approach allows the design and synthesis of a variety of tetrahydrocyclobuta[c]quinolin-3(1H)-ones, in yields ranging between 20–99 %, and with excellent regio- and diastereoselectivity. Moreover, it was demonstrated that the intramolecular [2+2]-cycloaddition of 1,7-enynes—after fragmentation of the cyclobutane ring—leads to enyne-metathesis-like products.
de Souza, Wanderson C.,Matsuo, Bianca T.,Matos, Priscilla M.,Correia, José Tiago M.,Santos, Marilia S.,K?nig, Burkhard,Paix?o, Marcio W.
supporting information
p. 3722 - 3728
(2021/02/03)

Synthesis of 1-Amino-2,2,2-trifluoroalkylphosphonates from Alkene-Tethered Trifluoroacetimidoyl Chlorides
The reaction of alkene-tethered trifluoroacetimidoyl chlorides with trialkyl phosphites furnishes 1-amino-2,2,2-trifluoroalkylphosphonates. The products were generated in moderate to good yields, and the scalability of this process was showcased. Partial hydrolysis of the phosphonate moiety was achieved. The cyclization is proposed to occur via formation of an imidoyl phosphonate intermediate that becomes susceptible to nucleophilic attack at nitrogen through the strong electron-withdrawing groups at the imidoyl carbon.
Rodríguez, José F.,Zhang, Anji,Arora, Ramon,Lautens, Mark
supporting information
p. 7540 - 7544
(2021/10/12)

Efficient synthesis of SCF3-substituted tryptanthrins by a radical tandem cyclization
Herein, we report a new, efficient and atom-economical strategy for the synthesis of SCF3-substituted tryptanthrin derivatives. These previously unreported derivatives were obtained by means of a radical tandem cyclization. The reaction was triggered by addition of a SCF3 radical to a carbon-carbon double bond and involved the formation of a C(sp3)-SCF3 bond, a C(sp2)-C bond, and a C(sp2)-N bond. This method has mild conditions and a wide range of substrates which is particularly useful for the preparation of substituted indolquinazoline derivatives that widely exist in many natural products, but are not easy to obtain by conventional approaches.
Guo, Jincheng,Hao, Yanan,Li, Gang,Li, Yongqiang,Liu, Yuxiu,Wang, Qingmin,Wang, Ziwen
supporting information
p. 1994 - 2001
(2020/03/23)

Palladium(ii)-catalyzed vinylic geminal double C-H activation and alkyne annulation reaction: Synthesis of pentafulvenes
The first transition-metal-catalyzed vinylic geminal double C(sp2)-H activation and di-substituted alkyne annulation reaction is reported. This palladium(ii)-catalyzed, amide directed reaction of vinylic compounds with di-substituted alkynes offers an efficient synthetic path to pentafulvenes, which are very important compounds because of their bioactivity and interesting optical properties. A FeCl3-mediated transformation of pentafulvenes to fluorescent cyclopenta[b]quinolines is also developed.
Phukon, Jyotshna,Gogoi, Sanjib
supporting information
p. 1133 - 1136
(2020/02/04)

Ynamide Smiles Rearrangement Triggered by Visible-Light-Mediated Regioselective Ketyl-Ynamide Coupling: Rapid Access to Functionalized Indoles and Isoquinolines
In the past decades, significant advances have been made on radical Smiles rearrangement. However, the eventually formed radical intermediates in these reactions are limited to the amidyl radical, except for the few examples initiated by a N-centered radical. Here, a novel and practical radical Smiles rearrangement triggered by photoredox-catalyzed regioselective ketyl-ynamide coupling is reported, which represents the first radical Smiles rearrangement of ynamides. This method enables facile access to a variety of valuable 2-benzhydrylindoles with broad substrate scope in generally good yields under mild reaction conditions. In addition, this chemistry can also be extended to the divergent synthesis of versatile 3-benzhydrylisoquinolines through a similar ketyl-ynamide coupling and radical Smiles rearrangement, followed by dehydrogenative oxidation. Moreover, such an ynamide Smiles rearrangement initiated by intermolecular photoredox catalysis via addition of external radical sources is also achieved. By control experiments, the reaction was shown to proceed via key ketyl radical and α-imino carbon radical intermediates.
Chen, Yang-Bo,Sun, Zhou,Wang, Ze-Shu,Ye, Long-Wu,Zhang, Hao-Wen,Zhu, Chunyin
supporting information
p. 3636 - 3644
(2020/03/06)

The synthesis of sulfonated 4: H -3,1-benzoxazines via an electro-chemical radical cascade cyclization
A new route for the synthesis of sulfonated 4H-3,1-benzoxazines has been accomplished by electrochemical radical cascade cyclizations of styrenyl amides with sulfonylhydrazines. This process demonstrates a wide substrate scope with diverse functional group compatibility under metal- and external oxidant-free conditions at ambient temperature.
He, Tian-Jun,Huang, Jing-Mei,Zhong, Wei-Qiang
supporting information
p. 2735 - 2738
(2020/03/17)

Palladium-Catalyzed Phosphoryl-Carbamoylation of Alkenes: Construction of Nonbenzylic C(sp3)?P(O)R2 Bonds via C(sp3)?Pd(II)?P(O)R2 Reductive Elimination
We report the first example of palladium-catalyzed phosphoryl-carbamoylation of alkene-tethered carbamoyl chlorides with P(O)H compounds. Both H-phosphinates and secondary phosphine oxides are compatible with this reaction. DPE-Phos was used as ligand to facilitate nonbenzylic C(sp3)?P bonds formations via C(sp3)?Pd(II)?P reductive elimination. By using this protocol, a range of phosphorylated oxindoles and lactams were obtained in moderate to good yields. (Figure presented.).
Chen, Chen,Sun, Wan,Yan, Yan,Yang, Fang,Wang, Yuebo,Zhu, Yan-Ping,Liu, Liying,Zhu, Bolin
supporting information
p. 2970 - 2975
(2020/07/06)

Experimental and Computational Studies on Cp*CyRh(III)/KOPiv-Catalyzed Intramolecular Dehydrogenative Cross-Couplings for Building Eight-Membered Sultam/Lactam Frameworks
Described herein is an unusual Cp*CyRh(III)-catalyzed intramolecular site-specific aryl C-H annulation, a highly chemoselective protocol providing direct access to eight-membered sultams/lactams with broad substrate/functional group tolerance. Experimental and computational studies reveal that such a transformation involves a unique PivOH-assisted aryl C-H activation/alkene insertion/β-H elimination/hydrogen-transfer process involving the Rh(III)-hydride species as the active intermediate with the concomitant release of H2 as the major byproduct, thus enabling the developed Cp*CyRh(III) catalysis with redox-neutral and highly atom-economical features.
Li, Liping,Gao, Hui,Sun, Ming,Zhou, Zhi,Yi, Wei
supporting information
p. 5473 - 5478
(2020/07/14)

Organocatalytic Atroposelective Construction of Axially Chiral N-Aryl Benzimidazoles Involving Carbon-Carbon Bond Cleavage
Axially chiral compounds widely occur in natural products, biologically active molecules, ligands, and catalysts, and their efficient and enantioselective synthesis is highly desirable. Herein, we report a novel method for the atroposelective construction of axially chiral N-aryl benzimidazoles with chiral phosphoric acid as the organocatalyst via reaction of N1-(aryl)benzene-1,2-diamines with multicarbonyl compounds. The present method provided the target products in high yields (up to 89percent) with excellent enantioselectivity (up to 98percent ee).
Man, Ningning,Lou, Zhenbang,Li, Yuming,Yang, Haijun,Zhao, Yufen,Fu, Hua
supporting information
p. 6382 - 6387
(2020/09/02)

Mn(III)-Mediated Regioselective 6-endo-trig Radical Cyclization of o-Vinylaryl Isocyanides to Access 2-Functionalized Quinolines
A Mn(III)-mediated radical cyclization reaction of o-vinylaryl isocyanides and arylboronic acids or diphenylphosphine oxides to access various 2-functionalized quinolines under mild conditions was developed. With the introduction of radical stabilizing substituents (e. g. aryl and methyl group) on vinyl group, this reaction provides a regiospecific 6-endo-trig radical cyclization of o-vinylaryl isocyanides, giving a number of structurally unique and biologically potential 2-functionalized quinoline derivatives.
Liu, Yan,Li, Shi-Jun,Chen, Xiao-Lan,Fan, Lu-Lu,Li, Xiao-Yun,Zhu, Shan-Shan,Qu, Ling-Bo,Yu, Bing
p. 688 - 694
(2020/01/02)

Enantioselective Copper-Catalyzed Borylative Cyclization with Cyclic Imides
An enantioselective borylative cyclization cascade utilizing cyclic imides has been developed. We employ a highly enantioselective borylcupration process that includes a 1,2-addition to a cyclic imide. The products contain a valuable hemiaminal and boronate handle for further elaborations within a congested framework. This work demonstrates the utility of cyclic imides as simple precursors to unlock access to sought-after polycyclic indolines. Futhermore, this report highlights the capability to harness reactive catalytic intermediates to exploit otherwise unreactive functional groups.
Whyte, Andrew,Torelli, Alexa,Mirabi, Bijan,Lautens, Mark
supporting information
p. 8373 - 8377
(2019/10/14)

Palladium(II)/Lewis acid cocatalyzed oxidative annulation of 2-alkenylanilines and propargylic esters: An access to benzo[ b]azepines
An attractive approach to valuable yet synthetically challenging benzo[b]azepines was established via palladium(II)/Lewis acid cocatalyzed oxidative [5 + 2] annulation of readily available 2-alkenylanilines and propargylic esters. The protocol features mild reaction conditions and good functional group tolerance, constituting an array of benzo[b]azepines in yields of 30-75%.
Qiao, Hong,Zhang, Shengjun,Li, Kangkang,Cao, Zhengqiang,Zeng, Fanlong
p. 10843 - 10851
(2019/09/12)

Cleavage of C-C Bonds for the Synthesis of C2-Substituted Quinolines and Indoles by Catalyst-Controlled Tandem Annulation of 2-Vinylanilines and Alkynoates
The strategy for the synthesis of C2-substituted indoles and quinolines from 2-vinylanilines and alkynoates through C-C bond cleavage is developed. With these general methods, 2-substituted indoles and quinolines can be accessed via tandem Michael addition and cyclization with no requirement of oxidant. This strategy not only provides a method for the synthesis C2-substituted indoles in good yields through the simultaneous cleavage of C=C and C=C bonds under metal-free conditions but also provides a simple method for the generation of the C2-substituted quinolines in moderate yields via Pd-catalyzed C=C bond cleavage.
Ni, Jixiang,Jiang, Yong,An, Zhenyu,Yan, Rulong
supporting information
p. 1534 - 1537
(2018/03/23)

Enantioselective Intramolecular Copper-Catalyzed Borylacylation
An enantioselective copper-catalyzed intramolecular borylacylation is reported. The reaction proceeds through an initial enantioselective borylcupration of the styrene, followed by a nucleophilic attack on the tethered carbamoyl chloride. The products, chiral borylated 3,3-disubstituted oxindoles, were generated in excellent yields and enantioselectivities. The versatile carbon–boron bond provides a platform for a wide array of diversification.
Whyte, Andrew,Burton, Katherine I.,Zhang, Jingli,Lautens, Mark
supporting information
p. 13927 - 13930
(2018/10/02)

Synthesis of 2-Quinolinones via a Hypervalent Iodine(III)-Mediated Intramolecular Decarboxylative Heck-Type Reaction at Room Temperature
A hypervalent iodine(III)-mediated intramolecular decarboxylative Heck-type reaction of 2-vinyl-phenyl oxamic acids has been developed. The unique ring-strain-enabled radical decarboxylation mechanism is preliminarily revealed. This protocol features metal-free reaction conditions and operational simplicity, allowing the lactamization of 2-vinylanilines using a readily accessible carbonyl source and the synthesis of various 2-quinolinones with excellent chemoselectivity at room temperature.
Fan, Huaqiang,Pan, Peng,Zhang, Yongqiang,Wang, Wei
supporting information
p. 7929 - 7932
(2019/01/04)

Water-Soluble Hypervalent Iodine(III) Having an I-N Bond. A Reagent for the Synthesis of Indoles
A readily accessible and bench-stable water-soluble hypervalent iodine(III) reagent (phenyliodonio)sulfamate (PISA) with an I-N bond was synthesized, and its structure was characterized by X-ray crystallography. With PISA, various indoles were synthesized via C-H amination of 2-alkenylanilines involving an aryl migration/intramolecular cyclization cascade with excellent regioselectivity in aqueous CH3CN. Notably, using this new method as the key step, not only two drug molecules, indometacin and zidometacin, but also another bioactive molecule, pravadoline, were synthesized.
Xia, Hai-Dong,Zhang, Yan-Dong,Wang, Yan-Hui,Zhang, Chi
p. 4052 - 4056
(2018/07/15)

Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles
A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline. (Figure presented.).
Zhao, Chun-Yang,Li, Kun,Pang, Yu,Li, Jia-Qing,Liang, Cui,Su, Gui-Fa,Mo, Dong-Liang
supporting information
p. 1919 - 1925
(2018/03/28)

Visible-Light Photocatalytic Decarboxylative Alkyl Radical Addition Cascade for Synthesis of Benzazepine Derivatives
A visible-light photocatalytic decarboxylative alkyl radical addition cascade reaction of acrylamide-tethered styrenes for the synthesis of benzazepine derivatives is described. This protocol features broad substrate scope, excellent functional group tolerance, and mild reaction conditions, affording the seven-membered rings in good yields. This method was also applied for efficient grafting of the benzazepine scaffold into the pharmaceutically active ursolic acid scaffold.
Zhao, Yu,Chen, Jia-Rong,Xiao, Wen-Jing
supporting information
p. 224 - 227
(2018/01/17)

Base-catalyzed thio-lactamization of 2-(1-arylvinyl)anilines with CS2 for the synthesis of quinoline-2-thiones
Here we show that the base-catalyzed thio-lactamization of 2-(1-arylvinyl)anilines with CS2 is a powerful methodology to synthesize quinoline-2-thiones. This thio-lactamization uses inexpensive and versatile 2-(1-arylvinyl)anilines, which are easily available from the reaction of amines and alkynes. Compared to the known strategy in the literature, this method features the advantages like a short synthesis step and easily available starting materials.
Wang, Tong-Lin,Liu, Xiao-Jun,Huo, Cong-De,Wang, Xi-Cun,Quan, Zheng-Jun
supporting information
p. 499 - 502
(2018/01/19)

Base-controlled chemoselectivity reaction of vinylanilines with isothiocyanates for synthesis of quinolino-2-thione and 2-aminoquinoline derivatives
Here, we report a base-controlled chemo-selective reaction of vinylanilines with alkyl/aryl isothiocyanates to afford quinolino-2-thione and 2-aminoquinoline derivatives. The quinolino-2-thiones could be obtained in high yields in the presence of Et3N. Particularly interesting is that the reaction could produce the 2-aminoquinolines in the presence of K3PO4 with high selectivity.
Zhang, Xi,Wang, Tong-Lin,Huo, Cong-De,Wang, Xi-Cun,Quan, Zheng-Jun
supporting information
p. 3114 - 3117
(2018/03/28)

Direct Electrophilic C?H Alkynylation of Unprotected 2-Vinylanilines
Unprotected aromatic amines can be used as directing groups in metal-catalyzed C?H alkynylations of alkenes. By using low amounts of an IrIIIcatalyst in combination with alkynylbenziodoxolones as electrophilic alkyne-transfer reagents, highly desirable 1,3-enynes were isolated in excellent yields of up to 98 % with Z stereoselectivity. A broad substrate scope as well as the high synthetic utility of the 1,3-enynes render this new method an efficient approach for the synthesis of five- and six-membered heterocycles. Further derivatizations of the 1,3-enynes to highly substituted quinolines through AuI- and N-bromosuccinimide-mediated exo-dig cyclizations were demonstrated.
Caspers, Lucien D.,Finkbeiner, Peter,Nachtsheim, Boris J.
supporting information
p. 2748 - 2752
(2017/03/08)

NH2-directed C-H alkenylation of 2-vinylanilines with vinylbenziodoxolones
The first directing-group-mediated C-H alkenylation with alkenyl-λ3-iodanes as electrophilic alkene-transfer reagents has been developed. The application of free aromatic amines as challenging but synthetically valuable directing groups in combination with an IrIII catalyst enabled the synthesis of highly desirable 1, 3- dienes in excellent yields of up to 98% with high to perfect (Z, E) stereoselectivity. A broad substrate scope and further synthetic modifications are demonstrated.
Boelke, Andreas,Caspers, Lucien D.,Nachtsheim, Boris J.
supporting information
p. 5344 - 5347
(2017/11/07)

Synthesis of Indoles from 2-Vinylanilines with PIFA or TFA and Quinones
The cyclizations involved in the synthesis of different indoles from 2-vinylanilines with PIFA {[bis(trifluoroacetoxy)iodo]benzene} and quinones have been developed under mild conditions. Various substituents on 2-vinylanilines induced good compatibility and gave the desired products in moderate to good yields.
Wu, Mingzhong,Yan, Rulong
supporting information
p. 729 - 733
(2017/03/21)

Tert -Butyl nitrite (TBN) as the N atom source for the synthesis of substituted cinnolines with 2-vinylanilines and a relevant mechanism was studied
A green method to synthesize cinnolines by 6π electrocyclic reaction with alkenyl amines and TBN has been developed. TBN plays a dual role both as a nitrogen atom source and an oxidant in this procedure. Relevant mechanism experiments reveal that the reaction proceeds through electrocyclic reaction and with diazo hydroxide as a key intermediate.
Pang, Xiaobo,Zhao, Lianbiao,Zhou, Dagang,He, Ping Yong,An, Zhenyu,Ni, Ji Xiang,Yan, Rulong
supporting information
p. 6318 - 6322
(2017/08/10)

Copper-catalyzed tandem aerobic oxidative cyclization for the ynthesis of polysubstituted quinolines via C(sp3)/C(sp2)-H bond functionalization
One-pot Cu-catalyzed tandem aerobic oxidative cyclization for the synthesis of quinolines from 2-vinylanilines/ 2-arylanilines and 2-methylquinolines via C(sp3)-H/C(sp2)- H bond functionalization has been developed. Dioxygen as an ideal oxidant has been employed for this transformation. The substrates bearing various functional groups perform well in this process and generate the desired products in moderate to good yields.
Pang, Xiaobo,Wu, Mingzhong,Ni, Jixiang,Zhang, Fuming,Lan, Jingfeng,Chen, Baohua,Yan, Rulong
p. 10110 - 10120
(2018/05/31)

Copper-mediated intramolecular aza-Wacker-type cyclization of 2-alkenylanilines toward 3-aryl indoles
A copper-mediated intramolecular aza-Wacker-type cyclization was developed for the direct and efficient synthesis of 3-aryl indoles using 2-alkenylanilines in moderate to good yields with good functional group compatibility. This strategy shows the high efficiency, operational simplicity as well as broad substrate scope.
Yang, Rui,Yu, Jin-Tao,Sun, Song,Zheng, Qingheng,Cheng, Jiang
supporting information
p. 445 - 448
(2017/01/11)

Lactamization of sp2C?H Bonds with CO2: Transition-Metal-Free and Redox-Neutral
The first direct use of carbon dioxide in the lactamization of alkenyl and heteroaryl C?H bonds to synthesize important 2-quinolinones and polyheterocycles in moderate to excellent yields is reported. Carbon dioxide, a nontoxic, inexpensive, and readily available greenhouse gas, acts as an ideal carbonyl source. Importantly, this transition-metal-free and redox-neutral process is eco-friendly and desirable for the pharmaceutical industry. Moreover, these reactions feature a broad substrate scope, good functional group tolerance, facile scalability, and easy product derivatization.
Zhang, Zhen,Liao, Li-Li,Yan, Si-Shun,Wang, Lei,He, Yun-Qi,Ye, Jian-Heng,Li, Jing,Zhi, Yong-Gang,Yu, Da-Gang
supporting information
p. 7068 - 7072
(2016/07/06)

Br?nsted Acid-Catalyzed Synthesis of N-Arylindoles from 2-Vinylanilines and Quinones
In the presence of a quinone, Br?nsted acid-catalyzed intramolecular C?N bond formation of o-vinylanilines by electrophilic cyclization was developed, giving the corresponding N-arylindoles in good to high yields. The reaction worked well for o-vinylanilines with terminal and internal C=C double bonds.
Zhang, Han-Ming,Gao, Zhong-Hua,Yi, Liang,Ye, Song
supporting information
p. 2671 - 2674
(2016/10/11)

Beyond a Protecting Reagent: DMAP-Catalyzed Cyclization of Boc-Anhydride with 2-Alkenylanilines
A novel rapid synthesis of quinolines from 2-alkenylanilines has been described; the reaction involves an unexpected DMAP-catalyzed cyclization of 2-alkenylanilines with di-tert-butyl dicarbonate (Boc2O, 2.0 equiv), and a series of tert-butyl quinolin-2-yl carbonate with various functional groups have been synthesized in good yields under mild conditions. Furthermore, the tert-butyl quinolin-2-yl carbonate can be easily converted into corresponding quinolinones and 2-(pseudo)haloquinolines.
Huang, Ya-Nan,Li, Yin-Long,Li, Jian,Deng, Jun
p. 4645 - 4653
(2016/07/06)

Copper-catalyzed trifluoromethylation of alkenes: Synthesis of trifluoromethylated benzoxazines
A simple base and ligand free copper catalyzed method for the construction of trifluoromethylated benzoxazines has been developed by using Umemoto's reagent. It involves the oxidative difunctionalization of alkenes through tandem C-O and C-CF3 bond formations. Furthermore, synthesized benzoxazines were selectively converted into trifluoromethylated allylic and (E)-vinylic benzamides by the treatment of KOtBu and CH3Li, respectively.
Jana, Sadhan,Ashokan, Athira,Kumar, Shailesh,Verma, Ajay,Kumar, Sangit
supporting information
p. 8411 - 8415
(2015/08/06)

Palladium-catalyzed direct coupling of 2-vinylanilines and isocyanides: An efficient synthesis of 2-aminoquinolines
Palladium-catalyzed oxidative coupling of 2-vinylanilines and isocyanides constitutes a direct, facile, and efficient approach to 2-aminoquinolines. The procedure, employing palladium acetate and silver carbonate, is attractive in terms of assembly efficiency, functional group tolerance, and operational simplicity. A variety of 2-aminoquinolines were prepared in good to excellent yields.
Wang, Lijie,Ferguson, Jamie,Zeng, Fanlong
supporting information
p. 11486 - 11491
(2015/12/04)

Synthesis of substituted γ-lactam via Pd(0)-catalyzed cyclization of alkene-tethered carbamoyl chloride
Pd(0)-catalyzed carboiodonation of but-3-enylcarbamic chloride has been developed with NaI as additive, which provides a ready access to substituted γ-lactam bearing an alkyl iodide group. This reaction features alkyl iodide reductive elimination as a key step in catalytic cycle, indicating the crucial role of additive NaI.
Chen, Chen,Hu, Jian,Su, Jianhua,Tong, Xiaofeng
supporting information
p. 3229 - 3231
(2014/06/09)

One-pot ring-closing metathesis/1,3-dipolar cycloaddition through assisted tandem ruthenium catalysis: Synthesis of a dye with isoindolo[2,1-a]quinoline structure
The one-pot tandem reaction of N-alkyl-N-allyl-2-vinylaniline derivatives with benzo- or naphthoquinones and a ruthenium-alkylidene catalyst leads to isoindolo[2,1-a]quinolines in a variety of colors, which can be altered by exchanging the substituent on the core heterocycle (see scheme). This reaction offers a new synthetic method for π-conjugated small molecules from simple aniline derivatives. Copyright
Arisawa, Mitsuhiro,Fujii, Yuki,Kato, Hiroshige,Fukuda, Hayato,Matsumoto, Takashi,Ito, Mika,Abe, Hiroshi,Ito, Yoshihiro,Shuto, Satoshi
supporting information
p. 1003 - 1007
(2013/03/13)

Amides as precursors of imidoyl radicals in cyclisation reactions
Amides have been successfully used as precursors of imidoyl radicals for radical cyclisation. The amides have been converted to imidoyl selanides via reaction with phosgene to yield imidoyl chlorides followed by reaction with potassium phenylselanide. Imidoyl selanides were reacted with tributyltin hydride (Bu3SnH) as the radical mediator with triethylborane or AIBN as initiators to yield imidoyl radicals for cyclisation reactions. Imidoyl radicals have been cyclised onto alkenes to yield 2,3-substituted-indoles and -quinolines and also onto pyrroles and indoles to give bi- and tricyclic heteroarenes.
Bowman, W. Russell,Fletcher, Anthony J.,Pedersen, Jan M.,Lovell, Peter J.,Elsegood, Mark R.J.,Hernández López, Elena,McKee, Vickie,Potts, Graeme B.S.
p. 191 - 203
(2007/10/03)

Novel formation of indoles and 3,1-benzoxazines from o-alkenylanilides and dimethyl(methylthio)sulfonium trifluoromethanesulfonate
The reaction of dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST) with o-allylphenol gave 2-methylthiomethyl-2,3-dihydrobenzofuran in 97% yield. The reaction of DMTST with N-tosyl-o-isopropenylanilide followed by the addition of aq sodium carbonate afforded N-tosyl-3-methylindole in 88% yield, whereas N-tosyl-o-vinylanilide afforded N-tosylindoline in 85% yield.
Okuma, Kentaro,Yasuda, Takumi,Takeshita, Itsuki,Shioji, Kosei,Yokomori, Yoshinobu
p. 8250 - 8254
(2008/02/08)

An Efficient Synthesis of 2,4-Disubstituted Quinolines by Electrophile-Mediated Cyclization Reactions of 2-Isocyanostyrene Derivatives
A novel quinoline synthesis starting with 2-isocyanostyrene derivatives is described. The treatment of 2-isocyanostyrene derivatives with aldehydes (or acetone) in the presence of a catalytic amount of diethyl ether-boron trifluoride afforded quinoline derivatives carrying a 1-hydroxyalkyl substituent at the 2-position. The use of acetaldehyde diethyl acetal or phenyloxirane as an electrophile under the same conditions gave the corresponding quinoline derivatives, carrying the 1-ethoxyethyl or 2-hydroxy-2-phenylethyl substituent at the 2-position, respectively. 2-Isocyanostyrene derivatives reacted with N,N-dimethyliminium salts without any catalyst to give 2-(1-dimethylaminoalkyl)quinolines.
Kobayashi, Kazuhiro,Takagoshi, Kenichi,Kondo, Shizuka,Morikawa, Osamu,Konishi, Hisatoshi
p. 553 - 559
(2007/10/03)

Intramolecular cyclization reactions of unsaturated amino Fischer chromium carbenes forming indoles and quinolines
A thermally induced intramolecular annulation reaction of N-(2-alkenylphenyl)amino substituted Fischer chromium carbenes has been extensively examined. The carbene complexes were prepared in moderate to good yields by reaction of 2-aminostyrenes with intermediately formed acyloxy substituted carbenes. Upon heating, the thermally labile carbenes decomposed producing indoles and quinolines as the major products. The product distribution was found to be highly dependent on the substitution pattern and electronic properties of the starting material, and on the solvent used.
S?derberg, Bj?rn C. G.,Shriver, James A.,Cooper, Seth H.,Shrout, Timothy L.,Helton, E. Scott,Austin, Lucinda R.,Odens, Herman H.,Hearn, Brian R.,Jones, Paula C.,Kouadio, Tiara N.,Ngi, Tan H.,Baswell, Rachel,Caprara, H. John,Meritt, Mark D.,Mai, Than T.
p. 8775 - 8791
(2007/10/03)

Novel approach to isoindolo[2,1-a]quinolines
An N-acyliminium ion approach towards the synthesis of isoindolo [2,1- a]quinolines by an intramolecular process is described.
Pigeon, Pascal,Decroix, Bernard
p. 2507 - 2516
(2007/10/03)

The reaction of N-phenylsulfonimidoyl chloride with trimethylsilylethene. A new route to 2-alkenylanilines
N-Phenylsulfonimidoyl chloride reacts with trimethylsilylethene in the presence of aluminum chloride to give two product benzothiazines, one of which has been desilylated. The silylated benzothiazine can be deprotonated and alkylated, sometimes with very high diastereocontrol. Upon treatment with fluoride, these silylated benzothiazines undergo desilylation with concomitant cleavage of the carbon-sulfur bond to give 2- alkenylsulfinanilides which can be hydrolyzed to the corresponding anilines.
Harmata, Michael,Kahraman, Mehmet,Jones, Darin E.,Pavri, Neville,Weatherwax, Susan E.
p. 9995 - 10006
(2007/10/03)

A general, regioselective synthesis of 2-alkenylanilines
Reduction of selected 2,1-benzothiazines with sodium amalgam leads to the formation of 2-alkenylanilines in high yield. The benzothiazines are readily available from the reaction of N-phenyl-S-(p-tolyl)sulfonimidoyl chloride with alkynes in the presence of aluminum chloride. The sulfonimidoyl chloride is derived from aniline, and the process described herein thus constitutes a high-yielding, regioselective functionalization of aniline.
Harmata,Kahraman
p. 713 - 716
(2007/10/02)

Pyrolyses of o-Alkoxy- and o-Alkylthio-N-Allylanilines and of Some Related O- and S-Allyl Compounds
The o-substituted allyl compounds (1)-(12) have been pyrolysed in order to generate aminyl, phenoxyl, and thiophenoxyl radicals with adjacent substituents.In all cases, products are formed by intramolecular hydrogen transfer from the substituent to the radical centre.This process may be followed by rearrangement to give an aldehyde, by heteroatom extrusion to give an alkene, or by ring formation to give five-membered ring heterocycles (Scheme 1, routes A, B1, and B2 respectively.The distribution of products formed by each route is dependent both on the nature of the o-substituent, and on the nature of the initial radical.
Cadogan, J. I. G.,Hickson, Clare L.,McNab, Hamish
p. 1885 - 1890
(2007/10/02)