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Communication | Special issue | Vol 10, No. 1, 1978, pp.261-264
Published online, 1st January, 1970
DOI: 10.3987/S-1978-01-0261
Reaction of β-Aminocrotonamides with α-Haloketones and α-Hydroxyketones

Tetsuzo Kato,* Takuo Chiba, Masaki Noda, and Makoto Sasaki

*Pharmaceutical Institute, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan


Reaction of bromoacetophenone (4) with β-aminocrotonamide (1) and β-aminocrotonanilide (2) gave 2-methyl-5-phenylpyrrole-3-carboxamide (6) and 2-methyl-5-phenylpyrrole-3-carboxanilide (7), respectively. Similarly, 2-chlorocyclohexanone (5) reacted with (1), (2) and β-amino-(N-methyl)crotonamide (3) to give 2-methyl-4,5,6,7-tetrahydroindole-3-carboxamide derivatives (8, 9 and 10).
Reactions of α-hydroxyketones such as benzoin (11) and acetoin (12) with (1), (2) and (3) afforded 2-methylpyrrole-3-carboxamide derivatives (13 - 18).