Facile Synthesis of 1-Substituted 2-Amino-3-cyanopyrroles: New Synthetic Precursors for 5,6-Unsubstituted Pyrrolo[2,3-d]pyrimidines
作者： Tun-Cheng Chien , Eric A. Meade , Jack M. Hinkley , Leroy B. Townsend
DOI: 10.1021/OL049207D
关键词:
摘要: 1-Benzyl-3-cyanopyrrole-2-carbonyl azide (5) underwent a Curtius rearrangement followed by quenching with alcohols to form the corresponding carbamates (6a−c). The 6a,b were unblocked give desired 2-amino-1-benzyl-3-cyanopyrrole (1a). A more facile procedure was subsequently developed for synthesis of 1-substituted 2-amino-3-cyanopyrroles. N-Substituted aminoacetaldehyde dimethyl acetals (7a−c) condensed malononitrile in presence p-toluenesulfonic acid monohydrate afford 2-amino-3-cyanopyrroles (1a−c).
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