Unexpected synthesis of indolo[1,2-c]quinazolines by a sequential Ugi 4CC-Staudinger-aza-Wittig-nucleophilic addition reaction

A new sequential Ugi-Staudinger-aza-Wittig-nucleophilic addition reaction was developed to construct indolo[1,2-c]quinazoline derivatives, starting from the easily accessible 2-azidobenzaldehyde, carboxylic acid, 2-acylaniline and isocyanide. It is noteworthy that this is the first report of the cyc...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2011-03, Vol.9 (5), p.1429-1436
Main Authors: He, Ping, Nie, Yi-Bo, Wu, Jing, Ding, Ming-Wu
Format: Article
Language:English
Subjects:
Aza Compounds - chemistry
Azides - chemistry
Crystallography, X-Ray
Cyclization
Indoles - chemistry
Models, Molecular
Molecular Structure
Quinazolines - chemical synthesis
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Summary:A new sequential Ugi-Staudinger-aza-Wittig-nucleophilic addition reaction was developed to construct indolo[1,2-c]quinazoline derivatives, starting from the easily accessible 2-azidobenzaldehyde, carboxylic acid, 2-acylaniline and isocyanide. It is noteworthy that this is the first report of the cyclization of the Ugi adduct to give a dihydroindole ring system with two quaternary carbon centers, via the nucleophilic addition reaction of the methine group to the carbonyl group.
ISSN:1477-0520
1477-0539
DOI:10.1039/c0ob00855a