Tetrahedron

X= Y-ZH Compounds as potential 1, 3-dipoles. Part 30. Cycloaddition of arylidene imines of α-amino esters to acetylenic dipolarophiles and pyrrole forming …

R Grigg, HQN Gunaratne, J Kemp

Index: Grigg, Ronald; Gunaratne, H. Q. Nimal; Kemp, James Tetrahedron, 1990 , vol. 46, # 18 p. 6467 - 6482

Full Text: HTML

Citation Number: 21

Abstract

Arylidene imines of α-amino esters undergo cycloaddition to ethyl phenylpropiolate, methyl propiolate and dimethyl acetylenedicarboxylate (ADE) on heating in toluene (110° C) or o- xylene (135-145° C). The reactions proceed via stereospecific azomethine ylide formation and give single 3-pyrroline cycloadducts in moderate to good yield. Reaction of certain of the imines with 2 mol. of ADE leads to a pyrroles formed by rearrangement. The ...