Syntheses of 3,4- and 1,4-dihydroquinazolines from 2-aminobenzylamine

Autor: Jimena E. Díaz, Silvia Ranieri, Nadia Gruber, Liliana R. Orelli
Jazyk: angličtina
Rok vydání: 2017
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 13, Iss 1, Pp 1470-1477 (2017)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.13.145
Popis: A straightforward strategy for the synthesis of dihydroquinazolines is presented, which allows for the preparation of 3,4- and 1,4-dihydroquinazolines with different substitution patterns from 2-aminobenzylamine (2-ABA) as common precursor. The required functionalization of both amino groups present in 2-ABA was achieved by different routes involving selective N-acylation and cesium carbonate-mediated N-alkylation reactions, avoiding protection/deprotection steps. The heterocycles were efficiently synthesized in short reaction times by microwave-assisted ring closure of the corresponding aminoamides promoted by ethyl polyphosphate (PPE).
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