Synthesis and Structure of 2-Arylamino-Substituted 4-(Dichloromethylidene)-3-Nitro-4 h -Pyrido[1,2- a ]Pyrimidines
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Synthesis and structure of 2-arylamino-substituted 4-(dichloromethylidene)-3-nitro-4H-pyrido[1,2-a]pyrimidines Irina А. Kolesnik1*, Sergey K. Petkevich1, Peter V. Kurman2, Alexander S. Lyakhov3, Ludmila S. Ivashkevich3, Hongwei Zhou4, Vladimir I. Potkin1 1
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, 13 Surganova St., Minsk 220072, Belarus; e-mail: [email protected] 2 Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, 5/2 Akademika V. F. Kuprevicha St., Minsk 220141, Belarus; e-mail: [email protected] 3 Scientific Research Institute for Physical Chemical Problems, Belarusian State University, 14 Leningradskaya St., Minsk 220006, Belarus; e-mail: [email protected] 4 College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001, China; e-mail: [email protected] Submitted May 12, 2020 Accepted June 19, 2020
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(9), 1187–1192
The reaction of 4-substituted anilines with 3,4,4-trichloro-1,1-bis(3,5-dimethyl-1H-pyrazol-1-yl)-2-nitrobuta-1,3-dienes led to 1-arylamino-3,4,4-trichloro-1-(3,5-dimethyl-1H-pyrazol-1-yl)-2-nitrobuta-1,3-dienes, which under the action of 2-aminopyridines underwent heterocyclization to the corresponding 2-arylamino-substituted 4-(dichloromethylidene)-3-nitro-4H-pyrido[1,2-a]pyrimidines. The molecular structure of 4H-pyrido[1,2-a]pyrimidine containing the (4-ethoxyphenyl)amine substituent at position 2 was determined by X-ray structural analysis. Keywords: arylamine, azole, nitrobutadiene, pyrido[1,2-a]pyrimidine, heterocyclization, nucleophilic substitution.
Pyrido[1,2-a]pyrimidines are among the privileged entities for drug discovery. They are inhibitors of enzymes elastase, reductase, urease, monoamine oxidase, and others which regulate the functioning of living systems in health and disease.1 This causes pyrido[1,2-a]pyrimidines to manifest a wide spectrum of biological action, in particular antiviral, antimicrobial, antitumor, antipsychotic, and antioxidant activity.2 Research on the chemistry of these compounds and the search for effective methods for the synthesis of their new derivatives for the creation of promising pharmaceutical substances remains of steady interest.3 One of the convenient approaches to the construction of the pyrido[1,2-a]pyrimidine system is based on the hetero0009-3122/20/56(9)-1187©2020 Springer Science+Business Media, LLC
cyclization of the available 1,1-bis(1H-benzotriazol-1-yl)3,4,4-trichloro-2-nitrobuta-1,3-diene (1) by the action of 2-aminopyridine (2). As a result of the reaction, 4-(dichloromethylidene)-3-nitro-4H-pyrido[1,2-a]pyrimidine 3 containing a benzotriazole fragment in position 2 of the pyrido[1,2-a]pyrimidine system is formed.4 In the study of the generality of this synthetic approach, we found that the reaction of 2-aminopyridine (2) with 3,4,4-trichloro-1,1-bis(3,5-dimethyl-1H-pyrazol-1-yl)-2-nitrobuta-1,3-diene (4) proceeds differently and leads to the formation of 4-(dichlor
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