Rapid formation of chemical complexity via a modified Biginelli reaction leading to dihydrofuran-2(3H)-one spiro-derivatives of triazolo[1,5-a]pyrimidine
Yükleniyor...
Tarih
2017
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Pergamon-Elsevier Science Ltd
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
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.
Açıklama
The work was supported by Artvin Coruh University research project (BAP-2012.F19.02.23) and Mevlana Exchange Program (MEV-2016-027).
Anahtar Kelimeler
Modified Biginelli reaction, Clean synthesis, Multicomponent reaction, Dihydrofuran-2(3H)-one, Triazolo[1,5-a]pyrimidine, Spiro-compounds
Kaynak
Tetrahedron Letters
WoS Q Değeri
Q3
Scopus Q Değeri
Q3
Cilt
58
Sayı
35
Künye
Gümüş, 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.
