Tetrahedron

Synthesis of novel bicyclic nitrogen heterocycles by the intramolecular dipolar cycloaddition reaction of nitrones with allenes and alkynes

A Padwa, M Meske, Z Ni

Index: Padwa, Albert; Meske, Michael; Ni, Zhijie Tetrahedron, 1995 , vol. 51, # 1 p. 89 - 106

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Citation Number: 43

Abstract

A study of the intramolecular dipolar cycloaddition reactions of a series of allenyl and alkynyl nitrones has been carried out. Phenylhydroxylamine readily reacts with o-(1, 2- propadienyloxy) benzaldehyde to give a dioxaazabicyclo [3.2. 1] octene. The intramolecular 3+ 2-cycloaddition of 2-(1, 2-propynyloxy) benzaldehyde and N-methylhydroxylamine was also studied. In this case, the major cycloadduct formed was identified as 4-methyl-2, 5- ...