cas 612-64-6, N-NITROSO-N-ETHYLANILINE | Articles data

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One-Pot Tandem ortho-Naphthoquinone-Catalyzed Aerobic Nitrosation of N-Alkylanilines and Rh(III)-Catalyzed C-H Functionalization Sequence to Indole and Aniline Derivatives
The nitroso group served as a traceless directing group for the C-H functionalization of N-alkylanilines, ultimately removed after functioning either as an internal oxidant or under subsequent reducing conditions. The unique ability of o-NQ catalysts to aerobically oxidize the N-alkylanilines without using solvents and stoichiometric amounts of oxidants has rendered the new opportunity to develop the telescoped catalyst systems without a need for directly handling the hazardous N-nitroso compounds.
Si, Tengda,Kim, Hun Young,Oh, Kyungsoo
p. 1152 - 1163
(2021/01/14)

Rhodium-catalyzed tandem acylmethylation/annulation ofN-nitrosoanilines with sulfoxonium ylides for the synthesis of substituted indazoleN-oxides
An atom-economical protocol for synthesizing indazoleN-oxides from readily availableN-nitrosoanilines and sulfoxonium ylides through the rhodium(iii)-catalyzed C-H activation and cyclization reaction is described here. This protocol employs nitroso as a traceless directing group. The transformation features powerful reactivity, tolerates various functional groups, and proceeds with moderate to good yields under an ambient atmosphere, providing a straightforward approach to access structurally diverse and valuable indazoleN-oxide derivatives. Importantly, this new annulation process represents a hitherto unobserved reactivity pattern for theN-nitroso group.
Cui, Xin-F,Huang, Guo-Sh
supporting information
p. 4014 - 4018
(2020/06/09)

Rh(iii)-catalyzed, hydrazine-directed C-H functionalization with 1-alkynylcyclobutanols: A new strategy for 1: H -indazoles
Rh(iii)-catalyzed coupling of phenylhydrazines with 1-alkynylcyclobutanols was realized through a hydrazine-directed C-H functionalization pathway. This [4+1] annulation, based on the cleavage of a Csp-Csp triple bond in alkynylcyclobutanol, provides a new pathway to prepare diverse 1H-indazoles under mild reaction conditions. This journal is
Zhang, Lei,Chen, Junyu,Chen, Xiahe,Zheng, Xiangyun,Zhou, Jian,Zhong, Tianshuo,Chen, Zhiwei,Yang, Yun-Fang,Jiang, Xinpeng,She, Yuan-Bin,Yu, Chuanming
supporting information
p. 7415 - 7418
(2020/07/15)

Rhodium(iii)-catalyzed indole synthesis at room temperature using the transient oxidizing directing group strategy
Rh-catalyzed reactions of N-alkyl anilines with internal alkynes at room temperature have been developed using an in situ generated N-nitroso group as a transient oxidizing directing group. Due to mild reaction conditions, this method enabled synthesis of a broad range of N-alkyl indoles, including even two indole-based medicinal compounds. Our work disclosed the feasibility of the transient oxidizing directing group strategy in C-H functionalization reactions, which possesses the potential to enhance overall step-economy and impart new reactivity patterns to substrates.
Shang, Yaping,Jonnada, Krishna,Yedage, Subhash Laxman,Tu, Hua,Zhang, Xiaofeng,Lou, Xin,Huang, Shijun,Su, Weiping
supporting information
p. 9547 - 9550
(2019/08/15)

Cp?Rh(iii) catalyzed: Ortho -halogenation of N -nitrosoanilines by solvent-controlled regioselective C-H functionalization
We present a novel, efficient, and regioselective method for the rhodium-catalyzed direct C-H ortho-halogenation of anilines that involves a removable N-nitroso directing group. This method featured mild reaction conditions, wide substrate scope, good functional group tolerance and satisfactory yields. To maintain the high ortho-regioselectivity and conversion, increasing the steric hindrance of the solvent was critical. Preliminary mechanistic studies suggest that C-H activation may be involved in the rate-determining step.
Peng, Qiujun,Hu, Jian,Huo, Jiyou,Yuan, Hongshun,Xu, Lanting,Pan, Xianhua
supporting information
p. 4471 - 4481
(2018/06/29)

N-Isocyanodialkylamines generated in situ for the Joullié–Ugi reaction with indolenines
N-Isocyanodialkylamines are rare isocyanide surrogates for the Ugi-type reactions. To avoid problems with instability and the obnoxious smell of these reagents, we optimized and employed a convenient protocol for in situ dehydration of N,N-dialkyl-N′-formyl hydrazines to give the respective N-isocyanodialkylamines which were utilized in the reaction with indolenines and acetic acid. The reaction was demonstrated to give modest to excellent yields of products incorporating the N-isocyanodialkylamine but not the carboxylic acid component.
Golubev, Pavel,Krasavin, Mikhail
supporting information
p. 3532 - 3536
(2018/08/29)

Rhodium(III)-Catalyzed Directed C?H Amidation of N-Nitrosoanilines and Subsequent Formation of 1,2-Disubstituted Benzimidazoles
An efficient rhodium-catalyzed direct C?H amidation of N-nitrosoanilines with 1,4,2-dioxazol-5-ones as amidating agents has been developed. This method featured mild reaction conditions, a wide substrate scope and satisfactory yields. Besides, the amidated products could be readily converted to pharmaceutically valuable 1,2-disubstituted benzimidazoles via an HCl-mediated deprotection/cyclization process in one pot.
Chen, Yanyu,Zhang, Rong,Peng, Qiujun,Xu, Lanting,Pan, XianHua
supporting information
p. 2804 - 2808
(2017/10/20)

An efficient synthesis of: N -nitrosamines under solvent, metal and acid free conditions using tert -butyl nitrite
Synthesis of various N-nitroso compounds from secondary amines is reported using tert-butyl nitrite (TBN) under solvent free conditions. Broad substrate scope, metal and acid free conditions, easy isolation procedure and excellent yields are few important features of this methodology. The acid labile protecting groups such as tert-butyldimethylsilyl (TBDMS) and tert-butyloxycarbonyl (Boc) as well as sensitive functional groups such as phenols, olefins and alkynes are found to be stable under the standard reaction conditions. Besides N-nitrosation, TBN is also found to be an efficient reagent in few other transformations including aryl hydrazines to aryl azides and primary amides to carboxylic acids under mild conditions.
Chaudhary, Priyanka,Gupta, Surabhi,Muniyappan, Nalluchamy,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
supporting information
p. 2323 - 2330
(2016/05/19)

Palladium-catalyzed ortho-acylation of N-Nitrosoanilines with α-oxocarboxylic acids: A convenient method to synthesize N-Nitroso ketones and indazoles
An efficient and mild protocol for regioselective synthesis of N-Nitroso aryl ketones by palladium-catalyzed direct acylation of arenes using N-Nitroso as directing groups is described. This reaction proceeded smoothly and could tolerate a variety of functional groups. Moreover, this chemistry offers a convenient access to a range of indazoles.
Zhang, Liang,Wang, Zhe,Guo, Peiyu,Sun, Wei,Li, Ya-Min,Sun, Meng,Hua, Chengwen
supporting information
p. 2511 - 2514
(2016/05/24)

Copper(II)-catalyzed oxidative N-nitrosation of secondary and tertiary amines with nitromethane under an oxygen atmosphere
The combination of a catalytic amount of Cu(OTf)2 and less than a stoichiometric amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) under an O2 atmosphere effectively promoted the N-nitrosation of both secondary aromatic/aliphatic amines and tertiary aromatic amines with nitromethane (CH3NO2) leading to the preparation of N-nitrosamine derivatives.
Sakai, Norio,Sasaki, Minoru,Ogiwara, Yohei
supporting information
p. 11638 - 11641
(2015/07/15)

Palladium-catalyzed oxidative C-H bond acylation of N-nitrosoanilines with toluene derivatives: A traceless approach to synthesize N-alkyl-2-aminobenzophenones
A palladium-catalyzed cascade cross-coupling of N-nitroso-anilines and toluene derivatives for the direct synthesis of N-alkyl-2-aminobenzophenones is described. N-nitroso groups in anilines can act as the traceless directing groups while toluene derivatives can serve as effective acyl precursors under mild reaction conditions.
Wu, Yinuo,Feng, Ling-Jun,Lu, Xiao,Kwong, Fuk Yee,Luo, Hai-Bin
supporting information
p. 15352 - 15354
(2015/01/08)

Rhodium(III)-catalyzed N-nitroso-directed C-H addition to ethyl 2-oxoacetate for cycloaddition/fragmentation synthesis of indazoles
RhIII-catalyzed N-nitroso-directed C-H addition to ethyl 2-oxoacetate allows subsequent construction of indazoles, a privileged heterocycle scaffold in synthetic chemistry, through the exploitation of reactivity between the directing group and installed group. The formal [2+2] cycloaddition/fragmentation reaction pathway identified herein, a unique reactivity pattern hitherto elusive for the N-nitroso group, emphasizes the importance of forward reactivity analysis in the development of useful C-H functionalization-based synthetic tools. The synthetic utility of the protocol is demonstrated with the synthesis of a tri-cyclic-fused ring system. The diversity of covalent linkages available for the nitroso group should enable the extension of the genre of reactivity reported herein to the synthesis of other types of heterocycles.
Chen, Jinsen,Chen, Pei,Song, Chao,Zhu, Jin
supporting information
p. 14245 - 14249
(2015/02/05)

Traceless directing strategy: Efficient synthesis of N-alkyl indoles via redox-neutral C-H activation
A general protocol for the synthesis of N-alkyl indoles has been developed via a redox neutral C-H activation strategy using a traceless nitroso directing group. A broad scope of substituted N-alkyl indoles has been prepared in good to excellent yields using a very simple Rh catalyst system in the absence of an external oxidant or any other additive. Good to excellent regioselectivity has been achieved for asymmetrically disubstituted acetylenes.
Wang, Chengming,Huang, Yong
supporting information
p. 5294 - 5297
(2013/11/06)

Iodide-catalyzed synthesis of N-nitrosamines via C-N cleavage of nitromethane
An iodide-catalyzed process to synthesize N-nitrosamines has been developed using TBHP as the oxidant. The mild catalytic system succeeded in cleaving the carbon-nitrogen bond in nitromethane. This methodology uses commercially available, inexpensive catalysts and oxidants and has a wide substrate scope and operational simplicity.
Zhang, Jie,Jiang, Jiewen,Li, Yuling,Wan, Xiaobing
p. 11366 - 11372
(2013/12/04)

Rhodium(III)-catalyzed N-nitroso-directed C-H olefination of arenes. High-yield, versatile coupling under mild conditions
N-Nitroso compounds are a versatile class of organic structures that allow expedient access to a diversity of synthetically useful architectures through demonstrated reactivities. We report herein the development of a Rh(III)-catalyzed N-nitroso-directed
Liu, Baoqing,Fan, Yang,Gao, Yang,Sun, Chao,Xu, Cheng,Zhu, Jin
supporting information
p. 468 - 473
(2013/02/23)

Nitromethane with IBX/TBAF as a nitrosating agent: Synthesis of nitrosamines from secondary or tertiary amines under mild conditions
Aliphatic or aromatic N,N-disubstituted nitrosamine was generated in fair to excellent yield from the reaction of a secondary or tertiary amine with o-iodoxybenzoic acid (IBX) or o-iodosylbenzoic acid (IBA)/R4NX (X = halide) and nitromethane. The product yield was strongly influenced by both the halide of R4NX and iodanes. IBX gave a higher yield than IBA, while the halides follow F- > Cl- > Br- ～ I-. Nitrous acid formed in situ from nitromethane and IBX (or IBA)/halides is likely responsible for the observed reaction.
Potturi, Hima K.,Gurung, Ras K.,Hou, Yuqing
experimental part
p. 626 - 631
(2012/02/16)

NOVEL HYDRAZINO-CYCLOBUT-3-ENE-1, 2-DIONE DERIVATIVES AS CXCR2 ANTAGONISTS
The present invention relates to novel hydrazino-cyclobut-3-ene-1,2-dione compounds of Formula (I) as selective CXCR2 antagonists, pharmaceutical compositions containing the novel compounds, as well as methods for treating or preventing chemokine mediated
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Page/Page column 33-34

(2010/09/03)

Design, synthesis, and evaluation of novel 3-amino-4-hydrazine-cyclobut-3-ene-1,2-diones as potent and selective CXCR2 chemokine receptor antagonists
We describe herein a novel series of 3-amino-4-hydrazine-cyclobut-3-ene-1,2-diones as potent and selective inhibitors against the CXCR2 chemokine receptor and IL-8-mediated chemotaxis of a CXCR2-expressing cell line. Furthermore, these alkyl-hydrazine series inhibitors such as 5b demonstrated acceptable metabolic stability when incubated in human and rat microsomes.
Liu, Shilan,Liu, Yinhui,Wang, Hongmei,Ding, YiLi,Wu, Hao,Dong, Jingchao,Wong, Angela,Chen, Shu-Hui,Li, Ge,Chan, Manuel,Sawyer, Nicole,Gervais, Francois G.,Henault, Martin,Kargman, Stacia,Bedard, Leanne L.,Han, Yongxin,Friesen, Rick,Lobell, Robert B.,Stout, David M.
scheme or table
p. 5741 - 5745
(2010/04/30)

Selective N-nitrosation of amines, N-alkylamides and N-alkylureas by N2O4 supported on cross-linked polyvinylpyrrolidone (PVP-N2O4)
N2O4 was supported on the cross-linked polyvinylpyrrolidone (PVP) to afford a solid, stable and recyclable nitrosating agent. This reagent shows excellent selectivity for N-nitrosation of dialkyl amines in the presence of diaryl-, arylalkyl-, trialkylamines and also for secondary amides in dichloromethane at room temperature under mild and heterogeneous conditions. Also N-nitroso-N-alkyl amides can be selectively prepared in the presence of primary amides and N-phenylamides under similar reaction conditions. Selective N-nitrosation or dealkylation and N-nitrosation of tertiary amines can also be performed by this reagent.
Iranpoor, Nasser,Firouzabadi, Habib,Pourali, Ali-Reza
p. 1591 - 1597
(2007/10/03)

Transnitrosation by N-aryl-N-nitrosoureas; NO-carrying O-nitrosoisourea
Transfer of nitroso groups, so-called transnitrosation, from aromatic N-nitroso compounds such as N-nitrosoureas, N-nitrosamides and N-nitrosamines, to aromatic amines or ureas was observed under non-acidic conditions at room temperature. Sterically hindered 3,3-dibenzyl-1-(4-tolyl)-1-nitrosourea (1a) rapidly nitrosates indoline, N-alkylanilines or 3-methyl-1-(4-tolyl)urea to give their N-nitroso derivatives. In the case of N,N-dimethylanilines, nitrosative demethylation occurs to give N-methyl-N-nitrosanilines. The transnitrosation is accelerated by electron-releasing groups on the nitroso acceptors, N-alkylanilines. The transnitrosation mechanism is considered to be as follows: N-nitrosourea (1) thermally decomposes to nitric oxide and ureidyl radical followed by formation of an O-nitrosoisourea intermediate (10), which acts as an NO-carrying agent and nitrosates anilines or ureas.
Tanno,Sueyoshi,Miyata
p. 1760 - 1767
(2007/10/02)

N-Dealkylation-N-nitrosation of Tertiary Aromatic Amines by n-Butyl Nitrite
N,N-Dialkyl aromatic amines with a variety of ring substituents are N-dealkylated and N-nitrosated efficiently by n-butyl nitrite/ammonium chloride/water at reflux temperature.Ring nitrosation was never observed, but minor amounts of m- and p-nitro amines and/or nitrosamines were formed in some cases.Ring nitration is rather a reaction of the initial substrate than a process occurring on formed nitrosamines.The leaving propensities of the initial N-substituents to yield nitrosamines were in the order benzyl >> methyl >> alkyl.Key Words: Nitrosamines; N-Dealkylation; N-Nitrosation; C-Nitration; Alkyl nitrite.
Verardo, Giancarlo,Giumanini, Angelo G.,Strazzolini, Paolo
p. 7845 - 7852
(2007/10/02)

Unusual Rate-limiting Proton Transfer in the Acid-catalysed Reactions of N-Nitroso Compounds
For both N-methyl-N-nitrosoaniline and N-nitrosodiphenylamine, the catalytic effect of halide ion, thiocyanate ion, and thiourea in the denitrosation reaction in acid solution disappears at high nucleophile concentrations.This suggests a change to an earlier rate-limiting step.The data, including the variation of rate constant with acidity, are quantitatively in accord with a reaction mechanism involving protonation of the nitosamine followed by nucleophilic attack, either stage being rate limiting, depending on the reactivity and concentration of the nucleophile.The kinetic solvent isotope effect kH2O/kD2O decreases from 1.59 at 0.43M-thiourea to 0.71 at 0.015M-thiourea, which is consistent with a change from general acid catalysis at high to specific hydrogen ion catalysis at low .Substituent effects at the amino-nitrogen atom and also in the 4-position of a phenyl substituent are very amall, the largest effect being a three-fold reduction in rate constant effected by a 4-NO2 group.These results are in accord with the known dipolar nature of nitrosamines.There is a close analogy between this system and the acid-catalysed cleavage reaction of carbamate derivatives.A similar mechanism is proposed involving a pre-association of the reactants forming a hydrogen-bonded intermediate.
Al-Kaabi, Sharifa S.,Hallett, Geoffrey,Meyer, Thomas A.,Williams, D. Lyn H.
p. 1803 - 1808
(2007/10/02)