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Synthesis of Fused Indolines by Interrupted Fischer Indolization in a Microfluidic Reactor.

ABSTRACT: 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.

SUBMITTER: Duong AT

PROVIDER: S-EPMC6322698 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Synthesis of Fused Indolines by Interrupted Fischer Indolization in a Microfluidic Reactor.

Duong Alexander Tuan-Huy AT Simmons Bryan J BJ Alam Mohammad Parvez MP Campagna Jesus J Garg Neil K NK John Varghese V

Tetrahedron letters 20181219 3

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 ald ...[more]

PMID: 30631216

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