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Rapid formation of chemical complexity via a modified Biginelli reaction leading to dihydrofuran-2(3H)-one spiro-derivatives of triazolo[1,5-a]pyrimidine
(Pergamon-Elsevier Science Ltd, 2017) Gümüş, Mustafa Kemal; Gorobets, Nikolay Yu.; Sedash, Yuriy V.; Shishkina, Svitlana V.; Desenko, Sergey M.
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.