Synthesis, X-ray and DFT studies of 6-halo-3-(hydroxymethyl)cinnolin-4(1H)-ones

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作   者：

Anastasia A. Babushkina;  Vladimir N. Mikhaylov;  Alexander S. Novikov;  Viktor N. Sorokoumov;  Maxim A. Gureev;  Mariya A. Kryukova;  Alexander O. Shpakov;  Irina A. Balova; 

作者机构：

Saint Petersburg State University;  Moscow 119991;  Research Center "Digital Biodesign and Personalized Healthcare";  Institute of Chemistry;  Russian Academy of Sciences;  44 Toreza Ave.;  Russia;  Saint Petersburg 199034;  8-2 Trubetskaya St.;  Saint Petersburg 194223;  Sechenov Institute of Evolutionary Biology and Biochemistry;  I. M. Sechenov First Moscow State Medical University;  7/9 Universitetskaya Embankment; 

关键词：

cinnolines;  Richter cyclization;  cross coupling;  tyrosine phosphatase 1В inhibitors;  bifurcated bonds;  DFT calculations; 

期刊名称：

Химия гетероциклических соединений: Всесоюз. науч. теорет. журн.

i s s n：

0132-6244

年卷期：

2022 年 58 卷 8/9 期

页   码：

432-437

页   码：

摘   要：

The Richter cyclization was used for the synthesis of 6-halo-3-(hydroxymethyl)cinnolin-4(1H)-ones. X-ray analysis revealed that these compounds exist as dimers in their crystal state, wherein two molecules are linked by intermolecular double and bifurcated hydrogen bonds that can explain their low solubility. Theoretical study of bifurcated hydrogen bonds responsible for the dimerization was carried out by DFT calculations as well as by topological analysis of the electron density distribution within the framework of Bader's theory.