Synlett 2023; 34(13): 1616-1620
DOI: 10.1055/a-2006-4703
letter

Iodine-Catalyzed One-Pot Multicomponent Synthesis of Pyrrolo/indolo[1,2-a]quinoxalines Substituted with ortho-Carbonyl Alkyl Benzoates/Benzoic Acids via Spirocyclic Ring Opening

Gorle Simhachalam
a   Technology Development Centre, APSL, Dr. Reddy’s Laboratories Ltd., Hyderabad 560049, India
b   Department of Chemistry, GIS, GITAM (Deemed to be University), Visakhapatnam 530045, India
,
L. Vaikunta Rao
b   Department of Chemistry, GIS, GITAM (Deemed to be University), Visakhapatnam 530045, India
,
Dasi Samsonu
c   Department of Chemistry, Andhra University, Visakhapatnam 530003, India
,
Akula Raghunadh
a   Technology Development Centre, APSL, Dr. Reddy’s Laboratories Ltd., Hyderabad 560049, India
› Institutsangaben


Preview

Abstract

An efficient iodine-catalyzed cascade coupling protocol was developed for the synthesis of tetracyclic and pentacyclic pyrrolo[1,2-a]quinoxaline and indolo[1,2-a]quinoxaline derivatives via the iodine-mediated oxidative Pictet–Spengler reaction of 2-(1H-pyrrol-1-yl)aniline or 2-(1H-indol-1-yl)aniline with ninhydrin followed by spirocyclic ring opening with alcohol/water. The target compounds were obtained in good-to-excellent yields with a broad substrate scope.

Supporting Information



Publikationsverlauf

Eingereicht: 05. Dezember 2022

Angenommen nach Revision: 03. Januar 2023

Accepted Manuscript online:
03. Januar 2023

Artikel online veröffentlicht:
31. März 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany