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Synthesis of 2‐aryl‐2,3‐dihydro‐4‐styrylpyrimidodiazepines in the reaction of 4,5,6‐triaminopyrimidine and 2,4,5,6‐tetraaminopyrimidine with diarylidenacetones
Author(s) -
Insuasty Braulio,
Insuasty Henry,
Quiroga Jairo,
Nogueras Manuel,
Sánchez Adolfo,
López M. Dolores
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.5570360418
Subject(s) - chemistry , regioselectivity , aryl , acetic acid , ethanol , catalysis , medicinal chemistry , stereochemistry , computational chemistry , organic chemistry , alkyl
New 6‐amino and 6,8‐diamino‐2‐aryl‐2,3‐dihydro‐4‐styryl‐1 H ‐pyrimido[4,5‐ b ][1,4]diazepines were obtained in the reaction of 2,4,5,6‐tetraaminopyrimidine 1a and 4,5,6‐triaminopyrimidine 1b with one equivalent of the diaryli dene acetones 2 in absolute ethanol with acetic acid as the catalyst. Structure analysis of 6‐amino and 6,8‐diamino‐2‐aryl‐2,3‐dihydro‐4‐styryl‐1 H ‐pyrimido[4,5‐ b ][1,4]diazepines 3a‐i, determined by detailed nmr measurements, reveals a high regioselectivity of this reaction.