4.4 Article

Rapid formation of chemical complexity via a modified Biginelli reaction leading to dihydrofuran-2(3H)-one spiro-derivatives of triazolo[1,5-a]pyrimidine

Journal

TETRAHEDRON LETTERS
Volume 58, Issue 35, Pages 3446-3448

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2017.07.071

Keywords

Modified Biginelli reaction; Clean synthesis; Multicomponent reaction; Dihydrofuran-2(3H)-one; Triazolo[1,5-a]pyrimidine; Spiro-compounds

Funding

  1. Artvin Coruh University research project [BAP-2012.F19.02.23]
  2. Mevlana Exchange Program [MEV-2016-027]

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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. (C) 2017 Elsevier Ltd. All rights reserved.

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