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

Edward E. Korshin; Leila A. Sabirova; Yakov A. Levin

doi:10.1055/s-0032-1316802

Synthesis, Table of Contents

Synthesis 2012; 44(22): 3512-3522
DOI: 10.1055/s-0032-1316802

paper

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

Edward E. Korshin*

^aDepartment of Organic Chemistry, the Weizmann Institute of Science, Rehovot 76100, Israel Fax: +972(8)9344142 Email: edward.korshin@weizmann.ac.il

^bArbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, 8 Arbuzov Str., Kazan 420088, Russian Federation

,

Leila A. Sabirova

^bArbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, 8 Arbuzov Str., Kazan 420088, Russian Federation

,

Yakov A. Levin

^bArbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, 8 Arbuzov Str., Kazan 420088, Russian Federation

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Abstract

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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.

Key words

nitrogen heterocycles - imidazole - cyclization - oxidation - dehydrogenation - heterogeneous catalysis

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References

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