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

ABSTRACT: 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).

SUBMITTER: Diaz JE 

PROVIDER: S-EPMC5550820 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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

Díaz Jimena E JE   Ranieri Silvia S   Gruber Nadia N   Orelli Liliana R LR  

Beilstein journal of organic chemistry 20170727

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 <i>N-</i>acylation and cesium carbonate-mediated <i>N-</i>alkylation reactions, avoiding protection/deprotection steps. The heterocycles  ...[more]

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