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Haloacetylated enol ethers. 13 . Synthesis of N ‐[1‐aryl(alkyl)‐3‐oxo‐4,4,4‐trichloro‐1‐buten‐1‐yl]‐ o ‐phenylenediamines and 2‐trichloromethyl‐4‐aryl‐3 H ‐1,5‐benzodiazepines
Author(s) -
Bonacorso Helio Gauze,
Bittencourt Sandra R. T.,
Wastowski Arci D.,
Wentz Alexandre P.,
Zanatta Nilo,
Martins Marcos A. P.
Publication year - 1999
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570360108
Subject(s) - chemistry , aryl , alkyl , enol , medicinal chemistry , intramolecular force , condensation , organic chemistry , stereochemistry , catalysis , physics , thermodynamics
The synthesis and isolation of the intermediates N ‐[1‐aryl(alkyl)‐3‐oxo‐4,4,4‐trichloro‐1‐buten‐1‐yl]‐ o ‐phenylenediamines 2a‐f and the corresponding 2‐trichloromethyl‐4‐aryl‐3 H ‐1,5‐benzodiazepines 3c‐g or benzimidazoles 4a‐b derivatives obtained from the intramolecular cyclization of 2a‐f or from direct cyclo‐condensation reaction of β‐alkoxyvinyl trichloromethyl ketones 1a‐g with o ‐phenylenediamine, is reported. Depending of the structure of the β‐alkoxyvinyl trichloromethyl ketones or the N ‐[1‐aryl(alkyl)‐3‐oxo‐4,4,4‐trichloro‐buten‐1‐yl]‐ o ‐phenylenediamines and the reactions conditions, benzimidazoles or 3 H ‐1,5‐benzodiazepines were obtained.