1,3-Dipolar Cycloaddition of Nitrile Imines to 2-Imino-thiazolo[3,2-a]pyrimidin-3-ones: Dipole-Initiated Thiazolone-Imidazolone Rearrangement

The 1,3-dipolar cycloaddition of nitrile imines to thiazolo[3,2-a]pyrimidine imines featuring both endocyclic and exocyclic C═N bonds was first reported. This reaction resulted in the regio- and stereoselective attachment of two dipole moieties, accompanied by peculiar skeletal rearrangements within the thiazolone fragment. Any products of only dipole addition cannot be isolated. The observed reactivity was explained using DFT protocols to investigate the cyclization mechanism of nitrile imines with thiazolo[3,2-a]pyrimidines. © 2025 American Chemical Society

Авторы
Petrova Juliana V. 1, 2 , Fil’Kina Maria E. 1 , Grishin Yuri 1 , Roznyatovsky V.A. 1 , Tafeenko Victor A. 1 , Nechaev Mikhail S. 3 , Ugrak Bogdan I. 4 , Dutova Tatyana Ya 4 , Savin Artemii M. 5 , Boldyrikhin Arsenii Y. 5 , Kukushkin Maxim E. 1 , Beloglazkina Elena K. 1
Journal
Journal of Organic Chemistry
Номер выпуска
42
Язык
English
Страницы
14861-14870
Статус
Published
Ссылка
Внешняя ссылка
DOI
10.1021/ACS.JOC.5C00670
Том
90
Год
2025
Организации
  • 1 Department of Chemistry, Lomonosov Moscow State University, Moscow, Moscow Oblast, Russian Federation
  • 2 RUDN University, Moscow, Moscow Oblast, Russian Federation
  • 3 A.V.Topchiev Institute of Petrochemical Synthesis, RAS, Moscow, Russian Federation
  • 4 N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
  • 5 Saint Petersburg National Research University of Information Technologies, Mechanics and Optics University ITMO, Saint Petersburg, Russian Federation
Ключевые слова
Addition reactions; Cycloaddition; 3-dipolar cycloaddition; Cyclizations; Regio-selective; Stereo-selective; Cyclization; 1 isopropyl n phenyl 1h pyrazole 3 carbohydrazonoyl chloride; 1 isopropyl n' phenyl 1h pyrazole 3 carbohydrazide; 1 methyl n phenyl 1h pyrazole 3 carbohydrazonoyl chloride; 1 methyl n' phenyl 1h pyrazole 3 carbohydrazide; 2 (4 tolylimino) 6,7 dihydro 5h thiazolo[3,2 a]pyrimidin 3(2h) one; 2 [(4 bromophenyl)imino] 6,7 dihydro 5h thiazolo[3,2 a]pyrimidin 3(2h) one; 2 [(4 chlorophenyl)imino] 6,7 dihydro 5h thiazolo[3,2 a]pyrimidin 3(2h) one; 2 [(4 methoxyphenyl)imino] 6,7 dihydro 5h thiazolo[3,2 a]pyrimidin 3(2h) one; 2 [(4 nitrophenyl)imino] 6,7 dihydro 5h thiazolo[3,2 a]pyrimidin 3(2h) one; 3,4,5 trimethoxy n phenylbenzohydrazonoyl chloride; 3,4,5 trimethoxy n' phenylbenzohydrazide; 4 chloro n phenylbenzohydrazonoyl chloride; 4 chloro n' phenylbenzohydrazide; 4 methyl n (4 nitrophenyl)benzohydrazonoyl chloride; 4 methyl n' (4 nitrophenyl)benzohydrazide; 4 nitro n phenylbenzohydrazonoyl chloride; 4 nitro n' phenylbenzohydrazide; carbon; imidazoline derivative; imine; iminothiazolo[3,2 a]pyrimidin 3 one derivative; n (4 nitrophenyl)benzohydrazonoyl chloride; n phenylacetohydrazonoyl chloride; n' (4 nitrophenyl)benzohydrazide; nitrile; nitrogen; ortho xylene; thiazole derivative; triphenylphosphine; unclassified drug; Article; carbon nitrogen bond; density functional theory; diastereoisomer; dipole; drug cytotoxicity; drug synthesis; HCT 116 cell line; human; human cell; stereoselectivity; Wittig reaction; X ray diffraction
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