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
收藏
页码：1357 / 1363
页数：7
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