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A General and Scalable Synthesis of Polysubstituted Indoles.

ABSTRACT: A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies.

SUBMITTER: Tejedor D

PROVIDER: S-EPMC7730962 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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A General and Scalable Synthesis of Polysubstituted Indoles.

Tejedor David D Diana-Rivero Raquel R García-Tellado Fernando F

Molecules (Basel, Switzerland) 20201128 23

A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies. ...[more]

PMID: 33260745

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