Synthesis of fused indolines by interrupted Fischer indolization in a microfluidic reactor

被引：2

作者：

Duong, Alexander Tuan-Huy ^{[1
]}

Simmons, Bryan J. ^{[2
]}

Alam, Mohammad Parvez ^{[1
,3
]}

Campagna, Jesus ^{[1
]}

Garg, Neil K. ^{[2
]}

John, Varghese ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Drug Discovery Lab, Dept Neurol, Mary S Easton Ctr Alzheimers Dis Res, Los Angeles, CA 90095 USA

[2] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

[3] Harvard Med Sch, Dept Genet, Boston, MA USA

来源：

TETRAHEDRON LETTERS | 2019年 / 60卷 / 03期

基金：

美国国家科学基金会;

关键词：

Flow chemistry; Interrupted Fischer indolization; Microfluidic reactor; (Aza)indoline; Latent aldehyde; FLOW CHEMISTRY; GREENER;

D O I：

10.1016/j.tetlet.2018.12.045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This study describes our development of a microfluidic reaction scheme for the synthesis of fused indoline ring systems found in several bioactive compounds. We have utilized a continuous-flow microfluidic reactor for the reaction of hydrazines with latent aldehydes through the interrupted Fischer indolization reaction to form fused indoline and azaindoline products. We have identified optimal conditions and evaluated the scope of this microfluidic reaction using various hydrazine and latent aldehyde surrogates. This green chemistry approach can be of general utility to rapidly produce indoline scaffolds and intermediates in a continuous manner. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：322 / 326

页数：5

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