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Novel synthesis of naphtho[2,1-b]pyrano pyrrolizidines and indolizidines through intramolecular 1,3-dipolar cycloaddition reaction

✍ Scribed by Subban Kathiravan; Devannah Vijayarajan; Raghavachary Raghunathan

Book ID: 104097707
Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 888 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.04.017

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✦ Synopsis

A facile synthesis of a series of naphtho[2,1-b]pyrano pyrrolizidines and indolizidines was accomplished in good yields in a one-pot reaction through intramolecular 1,3-dipolar cycloaddition of azomethine ylides with Baylis-Hillman adducts as dipolarophiles. The protocol is applicable to a wide variety of photochromic and biologically active napthopyrano products. The regio and stereochemical outcome of the cycloaddition reaction was ascertained by X-ray crystallographic study of some of the products.

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