1,2,4-Triazines and Calcium Carbide in the Catalyst-Free Synthesis of 2,3,6-Trisubstituted Pyridines and Their D-, 13 C-, and Doubly D2 -13 C2 -Labeled Analogues

Vladimir V Voronin; Mikhail V Polynski; Maria S Ledovskaya

doi:10.1002/asia.202300781

1,2,4-Triazines and Calcium Carbide in the Catalyst-Free Synthesis of 2,3,6-Trisubstituted Pyridines and Their D-, ¹³ C-, and Doubly D₂ -¹³ C₂ -Labeled Analogues

Chem Asian J. 2023 Dec 1;18(23):e202300781. doi: 10.1002/asia.202300781. Epub 2023 Nov 2.

Authors

Vladimir V Voronin¹, Mikhail V Polynski^{1

2}, Maria S Ledovskaya¹

Affiliations

¹ Saint Petersburg State University, Institute of Chemistry, Universitetsky Prospect 26, Saint Petersburg, 198504, Russia.
² Current address: National University of Singapore, Department of Chemical and Biomolecular Engineering, 4 Engineering Drive 4, Singapore, 117585, Singapore.

PMID: 37843978
DOI: 10.1002/asia.202300781

Abstract

A novel synthetic approach to 2,3,6-trisubstituted pyridines, their 4,5-dideuterated derivatives, 4,5-¹³ C₂ - and doubly-labeled D₂ -¹³ C₂ -pyridines has been developed using catalyst-free [4+2] cycloaddition of 1,2,4-triazines and in situ generated acetylene or labeled acetylene. Calcium carbide and water or deuterium oxide were used for the in situ generation of acetylene and dideuteroacetylene. Calcium carbide-¹³ C₂ in the mixture with water or deuterium oxide was applied as ¹³ C₂ -acetylene and D₂ -¹³ C₂ -acetylene source.

Keywords: alkynes; carbides; cycloaddition; isotopic labeling; nitrogen heterocycles.

Abstract

Grants and funding