The role of the carbonyl group in the intermolecular 1, 3-cycloaddition of azido (2-heteroaryl) methanones with activated olefins

P Zanirato

Index: Zanirato, Paolo Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 12 p. 1420 - 1425

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Citation Number: 10

Abstract

Treatment of the azido (2-heteroaryl) methanones 1–5 with methyl (E)-3-pyrrolidinoprop-2- enoate at room temperature yielded the methyl 1, 2, 3-triazolecarboxylate 6 and (2- heteroaryl)(pyrrolidino) methanones 1a–5a via an unusual 1, 3-cycloaddition reaction. Analogous reactions of the azidomethanones 1 and 2 with the dipolarophiles methyl crotonate, methyl propiolate or methyl but-2-ynoate failed. In contrast, the strained 5- ...