由2,4-戊二烯腈和异腈类化合物发散合成2,3-二氢-1H-吡咯、3-烷基-1H-吡咯和3-烯基-1H-吡咯。

Divergent synthesis of 2,3-dihydro-1H-pyrroles, 3-alkyl-1H-pyrroles and 3-alkenyl-1H-pyrroles from 2,4-pentadienenitriles and isocyanides.

作者信息

Xin Xiaoqing, Liu Xu, Zhang Dingyuan, Zhang Rui, Liang Yongjiu, Han Fushe, Dong Dewen

机构信息

Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, P. R. China.

出版信息

Org Biomol Chem. 2014 Aug 7;12(29):5477-83. doi: 10.1039/c4ob00912f.

DOI:10.1039/c4ob00912f

PMID:24943054

Abstract

An efficient and divergent one-pot synthesis of 2,3-dihydro-1H-pyrroles, 3-alkyl-1H-pyrroles and 3-alkenyl-1H-pyrroles from readily accessible 2,4-pentadienenitriles with isocyanide based on reaction condition selection has been described. The reaction of 2,4-pentadienenitriles with ethyl isocyanoacetate undergoes a formal [2 + 3] annulation either to generate 2,3-dihydro-1H-pyrroles in the presence of DBU (0.3 equiv.) in EtOH at room temperature or to give 3-alkyl-1H-pyrroles in the presence of DBU (2.0 equiv.) in EtOH under reflux. Moreover, the 2,3-dihydro-1H-pyrroles could be converted to 3-alkenyl-1H-pyrroles with DDQ as an oxidant.

摘要

本文描述了一种高效、多样的一锅法合成方法，该方法基于反应条件的选择，使用异腈从易于获得的2,4-戊二烯腈合成2,3-二氢-1H-吡咯、3-烷基-1H-吡咯和3-烯基-1H-吡咯。2,4-戊二烯腈与异氰基乙酸乙酯的反应通过形式上的[2 + 3]环化反应进行，在室温下于乙醇中，在DBU（0.3当量）存在下生成2,3-二氢-1H-吡咯；或在回流条件下于乙醇中，在DBU（2.0当量）存在下生成3-烷基-1H-吡咯。此外，以DDQ作为氧化剂，2,3-二氢-1H-吡咯可转化为3-烯基-1H-吡咯。