Synthesis 2012; 44(22): 3512-3522
DOI: 10.1055/s-0032-1316802
paper
© Georg Thieme Verlag Stuttgart · New York

An Expedient Synthesis of 5-Substituted Imidazo[1,2-c]quinazolines

Edward E. Korshin*
a  Department of Organic Chemistry, the Weizmann Institute of Science, Rehovot 76100, Israel   Fax: +972(8)9344142   eMail: edward.korshin@weizmann.ac.il
b  Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, 8 Arbuzov Str., Kazan 420088, Russian Federation
,
Leila A. Sabirova
b  Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, 8 Arbuzov Str., Kazan 420088, Russian Federation
,
Yakov A. Levin
b  Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, 8 Arbuzov Str., Kazan 420088, Russian Federation
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Publikationsverlauf

Received: 02. August 2012

Accepted after revision: 21. September 2012

Publikationsdatum:
17. Oktober 2012 (online)


Abstract

An efficient three-step synthesis of 5-substituted 2,3-dihydroimidazo[1,2-c]quinazolines and imidazo[1,2-c]quinazolines was elaborated. 2-(2-Aminophenyl)-4,5-dihydro-1H-imidazole, prepared by phosphorus pentasulfide catalyzed condensation of 2-aminobenzonitrile with ethylenediamine, smoothly reacted with aldehydes to give the corresponding 2,3,5,6-tetrahydroimidazo[1,2-c]quinazolines. The CH–NH fragments of the latter were subjected to selective oxidative dehydrogenation with one equivalent of potassium permanganate on silica gel to give 2,3-dihydroimidazo[1,2-c]quinazolines. With two equivalents of potassium permanganate on silica gel, a one-pot exhaustive dehydrogenation to imidazo[1,2-c]quinazolines was accomplished.

 
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