Synthesis of 2-azido-4-chloro-6-phenylpyrimidine-5-carbaldehyde and its transformations in DMSO

Synthesis of 2-azido-4-chloro-6-phenylpyrimidine-5-carbaldehyde and its transformations in DMSO Full article

Journal

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

Output data

Year: 2024, Volume: 73, Number: 7, Pages: 2014-2022 Pages count : 9 DOI: 10.1007/s11172-024-4321-8

Tags

pyrimidine carbaldehydes; tetrazolo[1,5-a]pyrimidines; 2-azidopiyrimidines; rearrangement; reaction mechanism; 13C isotopic label; azido-tetrazole tautomerism; NMR spectroscopy; X-ray diffraction; the Vilsmeier–Haack reaction

Authors

Aleksandrova N.V. ¹ , Nikolaenkova E.B. ¹ , Gatilov Yu.V. ¹ , Mamatyuk V.I. ¹ , Krivopalov V.P. ¹

Affiliations

1	N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences

2-Azido-4-chloro-6-phenylpyrimidine-5-carbaldehyde was synthesized by the Vilsmeier–Haack reaction. In DMSO, it transforms into 7-oxo-5-phenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carbaldehyde and then undergoes isomerization recyclization into 6-benzoyltetrazolo[1,5-a]pyrimidin-7(4H)-one. The structures of the obtained compounds were determined by NMR spectroscopy and X-ray diffraction.

Aleksandrova N.V. , Nikolaenkova E.B. , Gatilov Y.V. , Mamatyuk V.I. , Krivopalov V.P.
Synthesis of 2-azido-4-chloro-6-phenylpyrimidine-5-carbaldehyde and its transformations in DMSO
Russian Chemical Bulletin. 2024. V.73. N7. P.2014-2022. DOI: 10.1007/s11172-024-4321-8 WOS Scopus

Александрова Н.В. , Николаенкова Е.Б. , Гатилов Ю.В. , Маматюк В.И. , Кривопалов В.П.
СИНТЕЗ 2-АЗИДО-6-ФЕНИЛ-4-ХЛОРПИРИМИДИН-5-КАРБАЛЬДЕГИДА И ЕГО ПРЕВРАЩЕНИЯ В ДМСО
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2024. Т.73. №7. С.2014-2022. РИНЦ

Submitted:	Nov 14, 2023
Accepted:	Dec 14, 2023
Published print:	Aug 31, 2024

Web of science	WOS:001303930000027
Scopus	2-s2.0-85202728786
OpenAlex	W4402095843