65817-54-1Relevant academic research and scientific papers
Synthesis of 1-(2-Aminovinyl)indoles and 1,3′-Biindoles by Reaction of 2,2-Diaryl-Substituted 2 H-Azirines with α-Imino Rh(II) Carbenoids
Khaidarov, Adel R.,Rostovskii, Nikolai V.,Zolotarev, Andrey A.,Khlebnikov, Alexander F.,Novikov, Mikhail S.
, p. 3743 - 3753 (2019/02/14)
An effective and operationally simple method for the preparation of 1-(2-(sulfonamido)vinyl)indoles (SAV-indoles) by the Rh(II)-catalyzed reaction of 2,2-diaryl-2H-azirines with 1-sulfonyl-1,2,3-triazoles has been developed. This method enables the stereo
Modular 2,3-diaryl-2: H -azirine synthesis from ketoxime acetates via Cs2CO3-mediated cyclization
Zhao, Mi-Na,Zhang, Wei,Wang, Xu-Cai,Zhang, Ying,Yang, De-Suo,Guan, Zheng-Hui
, p. 4333 - 4337 (2018/06/21)
A modular 2H-azirine synthesis from ketoxime acetates via Cs2CO3-mediated cyclization has been developed. The reaction utilizes easily available starting materials and provides a general synthetic route to 2,3-diaryl-2H-azirines in good to excellent yields under mild conditions, which is complementary to the conventional approaches for the synthesis of 2H-azirines. A gram-scale reaction was performed to demonstrate the scale-up applicability of this synthetic method. Importantly, 2H-azirines can be efficiently converted to various azaheterocycles.
Synthesis method of azacyclopropene compound
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Paragraph 0018; 0020, (2018/11/04)
The invention discloses a synthesis method of an azacyclopropene compound represented as the formula (II). In the presence of alkali, the compound is prepared through an intramolecularly nucleophiliccyclization reaction to an oxime ester derivative represented in the formula (I); the R1 is selected from C1-C3 alkyl groups, phenyl group, substituted phenyl groups and naphthyl groups, wherein substituent groups in the substituted phenyl groups are selected from halogens, C1-C6 alkyl groups, C1-C6 alkoxyl groups, and cyclohexyl group; the R2 is selected from hydrogen and phenyl group; the R3 isselected from hydrogen, C1-C6 alkyl groups, and halogens. The method has gentle reaction conditions, low production cost, wide application range and high yield, and may be a simple new approach for synthesis of azacyclopropene compounds having medicinal activities.
An unexpected disproportional reaction of 2H-azirines giving (1E,3Z)-2-aza-1,3-dienes and aromatic nitriles in the presence of nickel catalysts
Okamoto, Kazuhiro,Mashida, Ayano,Watanabe, Masahito,Ohe, Kouichi
supporting information; experimental part, p. 3554 - 3556 (2012/06/18)
An unprecedented nickel-catalysed disproportional reaction of 2,3-diaryl-2H-azirines forming azabutadienes and aromatic nitriles was discovered. This reaction involves the cleavage of two bonds of the 2H-azirine framework, which provides a novel type of transformation of 2H-azirines.
Fe(II)-catalyzed amination of aromatic C-H bonds via ring opening of 2 H-azirines: Synthesis of 2,3-disubstituted indoles
Jana, Samaresh,Clements, MacK D.,Sharp, Barry K.,Zheng, Nan
supporting information; experimental part, p. 3736 - 3739 (2010/11/03)
A general method for the synthesis of 2,3-disubstituted indoles is described. The key feature of this method is the amination of aromatic C-H bonds via FeCl2-catalyzed ring opening of 2H-azirines. The method tolerates a variety of functional groups such as Br, F, NO2, OMe, CF3, OTBS, alkenes, and OPiv. The method can also be extended to synthesize azaindoles.
Rh(II)-catalyzed isomerization of 2-aryl-2H-azirines to 2,3-disubstituted indoles
Chiba, Shunsuke,Hattori, Gaku,Narasaka, Koichi
, p. 52 - 53 (2007/10/03)
Various 2,3-disubstituted indoles are synthesized by Rh 2(OCOCF3)4-catalyzed isomerization of 2-aryl-2H-azirines. Copyright
The Neber route to substituted indoles
Taber, Douglass F.,Tian, Weiwei
, p. 1058 - 1059 (2007/10/03)
Two complementary procedures have been developed for the conversion of the oximes of α-aryl ketones to azirines. On heating, the azirines rearrange smoothly to the corresponding indoles. The overall transformation offers a versatile route to indoles, complementary to the Fischer indole synthesis. Copyright
Steady-State and Laser Photolysis Studies of Substituted 2H-Azirines. Spectroscopy, Absolute Rates, and Arrhenius Behavior for the Reaction of Nitrile Ylides with Electron Deficient Olefins
Padwa, Albert,Rosenthal, Robert J.,Dent, William,Filho, Pedro,Turro, Nicholas J.,et al.
, p. 3174 - 3180 (2007/10/02)
The photobehavior of 2,2-diphenyl-3-methyl-2H-azirine (15) and 2-methyl-2,3-diphenyl-2H-azirine (14) was investigated in solution at 298 K.Both azirines undergo ready ring opening on exposure to UV light to give nitrile ylides which can be trapped with me
