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

作者：Kathiravan Subban; Vijayarajan Devannah; Raghunathan Raghavachary^*

来源：Tetrahedron Letters, 2010, 51(23): 3065-3070.

DOI：10.1016/j.tetlet.2010.04.017

• Pyrrolizidines
• Indolizidines
• 1,3-Dipolar cycloaddition
• Azomethine ylides
• Baylis-Hillman adduct

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 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.

• 出版日期2010-6-9