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Microwave‐assisted synthesis of new regioisomeric 6,7‐dihydroindeno[1,2‐ e ]pyrimido[4,5‐ b ][1,4]diazepin‐5(5a H )‐ones
Author(s) -
Insuasty Braulio,
Orozco Fabián,
Garcia Angélica,
Quiroga Jairo,
Abonia Rodrigo,
Nogueras M.,
Cobo Justo
Publication year - 2008
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.5570450616
Subject(s) - chemistry , reagent , microwave irradiation , aryl , microwave , ring (chemistry) , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , alkyl , physics , quantum mechanics
Novel 11‐amino‐6‐aryl‐6,7‐dihydroindeno[1,2‐ e ] pyrimido[4,5‐ b ][1,4]diazepin‐5(5a H )‐ones 4a‐f were prepared regioselectively by the tricomponent reaction of 4,5,6‐triaminopyrimidine 1, 1,3‐indandione 2 and aromatic aldehydes 3a‐f. The bicomponent approach, using 2,4,5,6‐tetraaminopyrimidine 5 and 2‐aryl‐ideneindandiones 6a‐f as reagents, afforded 9,11‐diamino‐6‐aryl‐6,7‐dihydroindeno[1,2‐ e ]pyrimido[4,5‐ b ]‐[1,4]diazepin‐5(5a H )‐ones 7a‐f in good yields and the regioisomeric 8,10‐diamino derivatives 8a‐c in lower yields. Both, bi‐ and tricomponent approaches were performed by microwave irradiation and all products were fully characterized by detailed NMR measurements.