First Synthesis of 3-Glycopyranosyl-1,2,4-Triazines and Some Cycloadditions Thereof

Autor:	Éva Bokor, Attila Ferenczi, Mahir Hashimov, Éva Juhász-Tóth, Zsófia Götz, Alshimaa Ibrahim Zaki, László Somsák
Jazyk:	angličtina
Rok vydání:	2022
Předmět:	C-glycosyl compound 1 2 4-triazine amidrazone IEDDA pyridine Organic chemistry QD241-441
Zdroj:	Molecules, Vol 27, Iss 22, p 7801 (2022)
Druh dokumentu:	article
ISSN:	1420-3049
DOI:	10.3390/molecules27227801
Popis:	C-glycopyranosyl derivatives of six-membered heterocycles are scarcely represented in the chemical literature and the title 3-glycopyranosyl-1,2,4-triazines are completely unknown. In this paper, the first synthesis of this compound class is accomplished by the cyclocondensation of C-glycosyl formamidrazones and 1,2-dicarbonyl derivatives. In addition, the synthesis of C-glycopyranosyl 1,2,4-triazin-5(4H)-ones was also carried out by the transformation of the above formamidrazones with α-keto-carboxylic esters. Inverse electron demand Diels–Alder reactions of 3-glycopyranosyl-1,2,4-triazines with a bicyclononyne derivative yielded the corresponding annulated 2-glycopyranosyl pyridines.
Databáze:	Directory of Open Access Journals
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