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Synthesis 2007(21): 3376-3384
DOI: 10.1055/s-2007-990809
DOI: 10.1055/s-2007-990809
PAPER
© Georg Thieme Verlag Stuttgart · New YorkSynthesis of Methyl 2-Amino-3H-1-benzazepine-4-carboxylates and 2-(Cyanomethyl)-2,3-dihydro-1H-indole-2-carboxylates from Morita-Baylis-Hillman Acetates of 2-(Acylamino)benzaldehydes
Further Information
Received
19 July 2007
Publication Date:
21 September 2007 (online)
Publication History
Publication Date:
21 September 2007 (online)

Abstract
Methyl 2-Amino-3H-1-benzazepine-4-carboxylates or methyl 2-(cyanomethyl)-2,3-dihydro-1H-indole-2-carboxylates were prepared from the reaction of 3-[2-formamido-, 2-acetamido-, or 2-(propanoylamino)phenyl]-substituted methyl 2-(cyanomethyl)propenoates with sodium methoxide in methanol, respectively. The latter were readily obtained from the Morita-Baylis-Hillman reaction of N-protected 2-aminobenzaldehydes with methyl acrylate followed by acetylation and cyanation.
Key words
Morita-Baylis-Hillman - 2-amino-3H-1-benzazepine - dihydroindole - N-protected 2-aminobenzaldehyde - 3-aryl-2-(cyanomethyl)propenoate
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