Diels-Alder reaction of 2-amino-substituted furans as a method for preparing substituted anilines

A Padwa, M Dimitroff, AG Waterson…

Index: Padwa, Albert; Dimitroff, Martin; Waterson, Alex G.; Wu, Tianhua Journal of Organic Chemistry, 1997 , vol. 62, # 12 p. 4088 - 4096

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Citation Number: 109

Abstract

5-Amino-2-furancarboxylic acid methyl ester undergoes a facile Diels-Alder cycloaddition with a variety of dienophiles to afford ring-opened cycloadducts that are readily dehydrated using BF3⊙ OEt2 to give polysubstituted anilines. In each case, the cycloaddition proceeds with high regioselectivity, with the electron-withdrawing group being located ortho to the amino group. The most favorable FMO interaction is between the HOMO of the furanamine ...