Synthesis of 2H-pyrrolo[3,4-C]quinoline via an Aldol/Van Leusen/Staudinger/aza-Wittig sequence

被引：6

作者：

Shi, Yu-Qing ^{[1
]}

Liao, Li-De ^{[1
]}

He, Ping ^{[1
,2
,4
]}

Hu, Yang-Gen ^{[3
,4
]}

Cheng, Hua ^{[1
]}

Wang, Song ^{[2
]}

Wu, Jun-Jun ^{[1
]}

机构：

[1] Coll Chem Engn & Food Sci, Xiangyang, Peoples R China

[2] Hubei Univ Arts & Sci, Hubei Key Lab Low Dimens Optoelect Mat & Device, Xiangyang, Peoples R China

[3] Hubei Univ Med, Hubei Key Lab Wudang Local Chinese Med Res, Shiyan, Peoples R China

[4] Hubei Univ Med, Taihe Hosp, Dept Pharm, Shiyan, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2016年 / 46卷 / 16期

基金：

中国国家自然科学基金;

关键词：

Aldol; van Leusen; Staudinger; aza-Wittig reaction; 2-azidobenzaldehyde; 2H-pyrrolo[3; 4-c]quinolones; pyrrole; ONE-POT SYNTHESIS; EFFICIENT SYNTHESIS; MULTICOMPONENT REACTIONS; TOSYLMETHYL ISOCYANIDE; FACILE SYNTHESIS; PLAKINIDINE D; DERIVATIVES; 1,5-ELECTROCYCLIZATION; IMIDAZOLES; ALKALOIDS;

D O I：

10.1080/00397911.2016.1204462

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An aldol/van Leusen/Staudinger/aza-Wittig reaction for the preparation of the derivatives of 2H-pyrrolo[3,4-c]quinolines from 2-azidobenzaldehyde, acetyl compounds, and tosylmethyl isocyanide was developed. The process involves an aldol condensation of 2-azidobenzaldehyde with acetyl compound in base, a van Leusen reaction to form the key pyrrole intermediates, and then a Staudinger and intramolecular aza-Wittig reaction occurred with the addition of triphenylphosphine to complete the formation of pyrrolo[3,4-c]quinoline ring in high yields. [GRAPHICS] .

引用

页码：1357 / 1363

页数：7

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