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Synthesis 2018; 50(18): 3723-3730
DOI: 10.1055/s-0037-1610439
paper
© Georg Thieme Verlag Stuttgart · New York

Regioselective Synthesis of Dihydro-1H-furo[b]indol-1-ones and Their Carbanionic Reactivity

Supriti Jana
Department of Chemistry, Indian Institute of Technology Kharagpur, 721302 India, Email: dmal@chem.iitkgp.ernet.in
,
Mausumi Bandyopadhyay
Department of Chemistry, Indian Institute of Technology Kharagpur, 721302 India, Email: dmal@chem.iitkgp.ernet.in
,
Dipakranjan Mal  *
Department of Chemistry, Indian Institute of Technology Kharagpur, 721302 India, Email: dmal@chem.iitkgp.ernet.in
› Author AffiliationsWe gratefully acknowledge the Council of Science & Industrial Research, New Delhi, India for financial support. S.J. is thankful to IIT KHARAGPUR for her research fellowship and contingency grant. We are also thankful to the DST-FIST for financial support for establishing an NMR facility.
Further Information

Publication History

Received: 23 April 2018

Accepted after revision: 28 May 2018

Publication Date:
10 July 2018 (online)

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Abstract

A general synthesis of 3,4-dihydro-1H-furo[b]indol-1-ones, representing a furanone-fused pyrrole unit, has been developed. The dehydrohalogenative cyclization of 4-aminofuranones was achieved by reaction with Pd(OAc)2 and DABCO in DMF. The corresponding N-protected indolones undergo alkylation at C3.

Key words

γ-lactone-fused heterocycles - furoindolones - regioselectivity - carbanions

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610439.
  • Supporting Information
 

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