Rapid formation of chemical complexity via a modified Biginelli reaction leading to dihydrofuran-2(3H)-one spiro-derivatives of triazolo[1,5-a]pyrimidine
AuthorGümüş, Mustafa Kemal
Gorobets, Nikolay Yu.
Sedash, Yuriy V.
Shishkina, Svitlana V.
Desenko, Sergey M.
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CitationGümüş, M. K., Gorobets, N. Y., Sedash, Y. V., Shishkina, S. V., & Desenko, S. M. (2017). Rapid formation of chemical complexity via a modified Biginelli reaction leading to dihydrofuran-2 (3H)-one spiro-derivatives of triazolo [1, 5-a] pyrimidine. Tetrahedron Letters, 58(35), 3446-3448.
The regio- and stereoselective, catalyst-free multicomponent synthesis of spiro-conjugated dihydrofuran-2(3H)-one/triazolo[1,5-a]pyrimidine derivatives in good to high yields via a Biginelli approach starting from ortho-substituted benzaldehydes, 3-amino-1.2,4-triazole and alpha-acetylbutyrolactone is reported. A plausible reaction mechanism for this transformation is discussed. The obtained heterocycles possess a drug-like conformationally restricted structure with defined stereochemistry and increased stability compared to other products obtained by this mode of the Biginelli reaction.