α-(Dialkylamino)-α-pyrrolylacetonitriles. A potpourri of useful synthetic transformations

BL Bray, JM Muchowski

Index: Bray, Brian L.; Muchowski, Joseph M. Canadian Journal of Chemistry, 1990 , vol. 68, # 8 p. 1305 - 1308

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Citation Number: 8

Abstract

α-(Dialkylamino)-α-(pyrrol-2-yl) acetonitriles (3) are versatile intermediates that are readily converted into regiochemically pure 2-bromo-6-dialkylamino-1-azafulvenes and 5-bromo-2- acylpyrroles (acyl= CHO, COR). In addition, 3 (R1= H), 4 (R1= H), and the β-substituted compound 9 are transformed easily and under mild conditions, via the corresponding α- methylthio compounds (eg, 7 a), into the methyl pyrrole carboxylates 8 a, 8 b, and 10, ...