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Multicomponent Domino Process to Oxa-bridged Polyheterocycles and Pyrrolopyridines, Structural Diversity Derived from Work-up Procedure by Rocio Gámez-Montaño; Eduardo González-Zamora; Pierre Potier; Jieping Zhu is a Chemistry article available to read on EtoBox.

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AbstractÐNovel three-component domino processes to polyheterocycles are developed. Reaction of an allylamine (3), an aldehyde (4) and an a-isocyanoacetamide (5) in methanol at room temperature provides an ef®cient access to oxa-bridged tricycle (1) as a single diastereoisomer. In this one-pot process, one C±N, one C±O and three C±C bonds are formed with concomitant creation of ®ve asymmetric centers. While isolable, the oxa-bridged tricycles (1) can be cleanly in-situ fragmented to pyrrolopyridines (2) under acidic conditions (tri ̄uoroacetic acid, 2788C), providing thus an unusual work-up derived structural diversity. The operational simplicity and excellent chemical yield make these novel heterocycle syntheses valuable in diversity-oriented high throughput synthesis.

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Author

Rocio Gámez-Montaño; Eduardo González-Zamora; Pierre Potier; Jieping Zhu

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

2002

Language

EN

Field

Chemistry (Physical Sciences)