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Synthesis and Structure Elucidation of New Regioisomeric 2‐Alkylamino‐6‐aryl‐8,9‐dihydropyrimido[4,5‐ b ][1,4]diazepin‐4(7 H )‐ones
Author(s) -
Insuasty Braulio,
Orozco Fabián,
Quiroga Jairo,
Abonía Rodrigo,
Nogueras Manuel,
Cobo Justo
Publication year - 2014
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.1778
Subject(s) - chemistry , microwave irradiation , aryl , irradiation , combinatorial chemistry , proton nmr , medicinal chemistry , stereochemistry , organic chemistry , alkyl , catalysis , physics , nuclear physics
Novel 2‐Alkylamino‐6‐aryl‐8,9‐dihydropyrimido[4,5‐ b ][1,4]diazepin‐4(7 H )‐ones 5a , 5b , 5c , 5d , 5e , 5f , 5g , 5h , 5i , 5j , 5k , 5l , 5m , 5n , 5o were prepared regioselectively by the reaction of 2‐alkylamino‐5,6‐diaminopyrimidin‐4(3 H )‐ones 3a , 3b , 3c and dimethylamino propiophenones (Mannich bases) 4a , 4b , 4c , 4d , 4e , 4f . The combination of conventional heating and microwave irradiation approaches provided the possibility of working with both stable and sensitive diaminopyrimidines by controlling parameters such as reaction rates, temperature, and power of irradiation. All products were fully characterized by detailed NMR measurements.