Synthesis of New Derivatives Benzo[4′,5′]imidazo[2′,1′:6,1]pyrido[2,3-d]pyrimidine


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Abstract

The reactions of 4-methyl- and (RS)-4,6-dimethyl-2-phenyl-5,6-dihydrobenzo[4′,5′]imidazo-[2′,1′:6,1]pyrido[2,3-d]pyrimidines and 4-methyl-5,6-dihydrobenzo[4′,5′]imidazo[2′,1:6,l]pyrido[2,3-d]pyrimi-din-2-ol with aromatic and heterocyclic aldehydes under various experimental conditions were studied. It was shown that the reaction with aldehydes upon boiling in acetic anhydride involves exclusively the 6-methylene group in the a-position to the benzimidazole fragment of the tetracycle and is accompanied by a 1,3-prototropic shift, which results in the formation of 6-aryl(hetaryl)methyl-4-methyl derivatives. The 4-methyl group in the substituted 2-phenyl(hydroxy)derivatives of 5,6-dihydrobenzo[4′,5′]imidazo[2′,1′:6,1]pyrido[2,3-d]pyrimidines reacts with aldehydes only under fusion conditions in the presence of ZnCl2. The structure of the synthesized compounds was confirmed by one- and two-dimensional (NOESY) 1H NMR spectroscopy and XRD analysis.

About the authors

A. A. Harutyunyan

Russian-Armenian (Slavic) University; Scientific Technological Center of Organic and Pharmaceutical Chemistry

Author for correspondence.
Email: harutyunyan.arthur@yahoo.com
Armenia, ul. Hovsep Emin 123, Yerevan, 0051; pr. Azatutyan 26, Yerevan, 0014

G. T. Gukasyan

Russian-Armenian (Slavic) University

Email: harutyunyan.arthur@yahoo.com
Armenia, ul. Hovsep Emin 123, Yerevan, 0051

H. A. Panosyan

Scientific Technological Center of Organic and Pharmaceutical Chemistry

Email: harutyunyan.arthur@yahoo.com
Armenia, pr. Azatutyan 26, Yerevan, 0014

R. A. Tamazyan

Scientific Technological Center of Organic and Pharmaceutical Chemistry

Email: harutyunyan.arthur@yahoo.com
Armenia, pr. Azatutyan 26, Yerevan, 0014

A. G. Ayvazyan

Scientific Technological Center of Organic and Pharmaceutical Chemistry

Email: harutyunyan.arthur@yahoo.com
Armenia, pr. Azatutyan 26, Yerevan, 0014

A. S. Grigoryan

Scientific Technological Center of Organic and Pharmaceutical Chemistry

Email: harutyunyan.arthur@yahoo.com
Armenia, pr. Azatutyan 26, Yerevan, 0014

G. G Danagulyan

Russian-Armenian (Slavic) University; Scientific Technological Center of Organic and Pharmaceutical Chemistry

Email: harutyunyan.arthur@yahoo.com
Armenia, ul. Hovsep Emin 123, Yerevan, 0051; pr. Azatutyan 26, Yerevan, 0014

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