Synthesis of some 2-aminofurans from cyanoacetone enolate and their rearrangement to 3-cyanopyrroles with ammonia

JF Blount, DL Coffen, DA Katonak

Index: Blount,J.F. et al. Journal of Organic Chemistry, 1978 , vol. 43, p. 3821 - 3824

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Citation Number: 26

Abstract

CN a COOEt a COCH, a CONH, b CONHBU-t a, b, c CONMe, C a and b encountered in the earlier examples. Compound 20 results from cyclization mode c followed by elimination of tert-butylamine from the tetrahedral intermediate. Finally, when the group Rz is a tertiary amide group, ie, dimethylamide, the chemistry reverts to the simple situation in which a single product is formed. Cyclization mode c prevails, and the hydroxyfuran 20 is obtained ...