Synthesis of New Derivatives Benzo[4′,5′]imidazo[2′,1′:6,1]pyrido[2,3-d]pyrimidine
- Authors: Harutyunyan A.A.1,2, Gukasyan G.T.1, Panosyan H.A.2, Tamazyan R.A.2, Ayvazyan A.G.2, Grigoryan A.S.2, Danagulyan G.G1,2
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Affiliations:
- Russian-Armenian (Slavic) University
- Scientific Technological Center of Organic and Pharmaceutical Chemistry
- Issue: Vol 55, No 11 (2019)
- Pages: 1698-1703
- Section: Article
- URL: https://journal-vniispk.ru/1070-4280/article/view/221359
- DOI: https://doi.org/10.1134/S1070428019110095
- ID: 221359
Cite item
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.
Keywords
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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