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Microwave-assisted synthesis of new regioisomeric 6,7-dihydroindeno[1,2-e]pyrimido[4,5-b][1,4]diazepin-5(5aH)-ones

✍ Scribed by Braulio Insuasty; Fabián Orozco; Angélica Garcia; Jairo Quiroga; Rodrigo Abonia; M. Nogueras; Justo Cobo

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
232 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

magnified image

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.

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