[4+1+1] Annulations of α-Bromo Carbonyls and 1-Azadienes toward Fused Benzoazaheterocycles

被引：44

作者：

Zeng, Rong ^{[1
]}

Shan, Changyu ^{[1
]}

Liu, Ming ^{[1
]}

Jiang, Kun ^{[1
]}

Ye, Ying ^{[1
]}

Liu, Tian-Yu ^{[1
]}

Chen, Ying-Chun ^{[1
,2
]}

机构：

[1] Third Mil Med Univ, Coll Pharm, Chongqing 400038, Peoples R China

[2] Sichuan Univ, Dept Med Chem, West China Sch Pharm, Chengdu 610041, Sichuan, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 07期

关键词：

AMMONIUM YLIDES; ORGANOCATALYTIC CYCLOPROPANATION; MEDIATED CYCLOPROPANATION; 3-EXO-TET CYCLIZATION; LEAVING GROUP; HETEROCYCLES; 1,3-DIHALOPROPANES; CYCLOADDITION; CONSTRUCTION; PYRIDINES;

D O I：

10.1021/acs.orglett.9b00598

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unexpected [4 + 1 + 1] annulation between alpha-bromo carbonyls and 1-azadienes, derived from 2-methylenebenzofuran-3(2H)-ones or 2-methylenebenzo[b]thiophene-3(2H)-ones, has been observed in the presence of DABCO and Cs2CO3. These reactions stand in contrast to the common [4 + 1] cyclization reactions of azadienes with the related sulfonium ylides. A range of fused benzofuro[3,2-b]pyridines and benzo[4,5]thieno[3,2-b]pyridines have been efficiently constructed in fair to excellent yields.

引用

页码：2312 / 2316

页数：5

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