Issue 25, 2016

Diversity oriented synthesis of β-carbolinone and indolo-pyrazinone analogues based on an Ugi four component reaction and subsequent cyclisation of the resulting indole intermediate

Abstract

A one-pot domino multicomponent reaction for the rapid, integrated and versatile synthesis of highly functionalized β-carbolinones (9a–9ab) and indolo-pyrazinones (10a–10ab) has been established. The reaction involves an Ugi-four component reaction of indole 2-carboxylic acid (1 or 16a–c), aryl or alkyl aldehyde (6a–p), isocyanide (3a–e), and aminoacetaldehyde dimethyl acetal (7) followed by in situ acid-mediated deprotection/activation/electrophilic cyclisation/and aromatisation. The products were obtained from Ugi adducts in good to excellent yield within short periods of 20–30 min at room temperature (35 °C). The potential of the methodology is proved by development of a diverse library of heterocyclic compounds with point and skeletal diversity. Moreover, the synthesis has also been accomplished using N-substituted derivatives of indole 2-carboxylic acid that delivers highly diverse N-substituted β-carbolinone (18a–l) heterocycles of medicinal importance.

Graphical abstract: Diversity oriented synthesis of β-carbolinone and indolo-pyrazinone analogues based on an Ugi four component reaction and subsequent cyclisation of the resulting indole intermediate

Supplementary files

Article information

Article type
Paper
Submitted
18 ⴷⵓⵊ 2015
Accepted
02 ⴱⵕⴰ 2016
First published
03 ⴱⵕⴰ 2016

RSC Adv., 2016,6, 21165-21186

Diversity oriented synthesis of β-carbolinone and indolo-pyrazinone analogues based on an Ugi four component reaction and subsequent cyclisation of the resulting indole intermediate

P. Purohit, A. K. Pandey, B. Kumar and P. M. S. Chauhan, RSC Adv., 2016, 6, 21165 DOI: 10.1039/C5RA27090A

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