Abstract
A novel and simple one-pot synthesis of 3-substituted 2,5,6,7-tetrahydro-1H-1,4-diazepin-2-ones from 1,2-diaza-1,3-dienes (DDs) and N-unsubstituted aliphatic 1,3-diamines is described. Here we also report a procedure to selectively obtain alkyl 5H-1,4-benzodiazepine-3-carboxylates from the DDs and 2-aminobenzylamine. Both processes occur by means of sequential 1,4-conjugated addition followed by regioselective 7-exo cyclization. The behavior of N-methyl- and N,N'-dimethyl-1,3-diaminopropanes toward the DDs furnished pyrazol-3-ones and bis-α-aminohydrazones, respectively.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkanes / chemistry
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Aza Compounds / chemistry
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Benzodiazepines / analysis
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Benzodiazepines / chemical synthesis*
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Carboxylic Acids / chemistry
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Chemistry, Pharmaceutical / methods*
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Chromatography, Thin Layer
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Cyclization
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Diamines / analysis
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Diamines / chemical synthesis*
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Drug Discovery
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Humans
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Hydrazones / chemical synthesis
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Magnetic Resonance Spectroscopy
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Molecular Mimicry
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Peptides / chemistry
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Psychotropic Drugs / analysis
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Psychotropic Drugs / chemical synthesis*
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Pyrazolones / chemical synthesis
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Stereoisomerism
Substances
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Alkanes
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Aza Compounds
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Carboxylic Acids
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Diamines
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Hydrazones
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Peptides
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Psychotropic Drugs
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Pyrazolones
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Benzodiazepines