Journal
RSC ADVANCES
Volume 6, Issue 25, Pages 21165-21186Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ra27090a
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Funding
- CSIR, New Delhi for Senior Research Fellowships (SRF)
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A one-pot domino multicomponent reaction for the rapid, integrated and versatile synthesis of highly functionalized beta-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 acidmediated 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 degrees 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 beta-carbolinone (18a-l) heterocycles of medicinal importance.
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