DMF as an amine source: iron-catalyzed cyclization of 2H-azirines to imidazoles

被引：1

作者：

Zhao, Mi-Na ^{[1
]}

Yang, Zi-Mo ^{[2
]}

Li, Lian-Qing ^{[1
]}

机构：

[1] Shaanxi Xueqian Normal Univ, Coll Chem & Chem Engn, Xian 710100, Shaanxi, Peoples R China

[2] Baoji Univ Arts & Sci, Coll Chem & Chem Engn, Shaanxi Key Lab Phytochem, Baoji 721013, Shaanxi, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2024年 / 60卷 / 14期

基金：

中国国家自然科学基金;

关键词：

CYCLOADDITION; ACCESS; CHLORIDES; PYRROLES;

D O I：

10.1039/d3cc06147g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel method has been developed for the synthesis of 1-methyl4,5-diaryl-1H-imidazoles through Fe(II)-catalyzed cyclization of 2H-azirines and N,N-dimethylformamide (DMF) as an amine source. This transformation involves the cleavage of C-N and C=N double bonds and the construction of new C-N and C=N double bonds. The reaction has readily available starting materials, a wide range of substrates and mild reaction conditions. In addition, the reaction also facilitated the convenient synthesis of 1-methyl-2,4,5-triaryl1H-imidazoles.

引用

页码：1904 / 1907

页数：4

共 50 条

[21] Conical intersections and photoreactions of 2H-azirines
Bornemann, C
Klessinger, M
CHEMICAL PHYSICS, 2000, 259 (2-3) : 263 - 271
[22] 3-Phosphorylated 2H-azirines
D. V. Lyamenkova
N. B. Viktorov
A. V. Dogadina
Russian Journal of General Chemistry, 2015, 85 : 500 - 501
[23] RETRACTION: Iron-Catalyzed Three-Component Reaction: Synthesis of Fluoroalkylated 2H-Azirines (Retraction Article) (Retraction of 10.1038/S41467-018-07985-2)
Ramkumar, Nagarajan
Van Meervelt, Luc
Van der Eycken, Erik V.
ORGANIC LETTERS, 2019, 21 (03) : 850 - 850
[24] Activated 2H-azirines as dienophiles and electrophiles
Gilchrist, TL
ALDRICHIMICA ACTA, 2001, 34 (02) : 51 - 55
[25] Recent approaches to the synthesis of 2H-azirines
Ramkumar, Nagarajan
Voskressensky, Leonid G.
Sharma, Upendra K.
Van der Eycken, Erik V.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2019, 55 (09) : 795 - 801
[26] A novel approach to substituted 2H-azirines
Katritzky, AR
Wang, MY
Wilkerson, CR
Yang, HF
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23): : 9105 - 9108
[27] A GENERAL SYNTHESIS OF 2H-AZIRINES FROM OLEFINS . FUSED AZIRINES
HASSNER, A
FOWLER, FW
TETRAHEDRON LETTERS, 1967, (16) : 1545 - &
[28] THERMAL-REACTIONS OF 2H-AZIRINES
TANIGUCHI, H
ISOMURA, K
TANAKA, T
HETEROCYCLES, 1977, 6 (9-10) : 1563 - 1568
[29] Copper-Promoted Oxidative Cyclization/Migration of Enaminone for Synthesis of Functionalized 2H-Azirines
Yang, Kun
Duan, Xiyan
Li, Junbo
Liu, Pu
Guo, Xuming
Li, Jun
Zhou, Huiyun
Liu, Ning
Liu, Jianwei
Wang, Shuangshuang
Li, Huixian
Du, Yazhen
Ma, Junying
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (04) : 1040 - 1045
[30] UNUSUAL REACTION BY PHOTOLYSIS OF 2H-AZIRINES
HIRAKAWA, K
ISOMURA, K
TANIGUCHI, H
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1979, (APR): : 444 - 444

← 1 2 3 4 5 →