Switchable Multicomponent Cyclization Reactions to Access Fluoroalkylated Dihydropyrimidines and Pyrimidines under Solvent‐Free Conditions

• Published in: Chinese journal of chemistry Vol. 42; no. 12; pp. 1394 - 1398
• Main Authors: Zuo, Wanqing, Zhu, Zhizhen, Cheng, Yu, Zuo, Lingling, Geng, Xiao, Li, Zhifang, Wang, Lei
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY‐VCH Verlag GmbH & Co. KGaA 15.06.2024; Wiley Subscription Services, Inc
• Subjects: Amidines; Chemical reactions; Enaminones; Environmental chemistry; Fluorine chemistry; Heterocycles; Hydrates; Multicomponent reactions; Pyrimidines; Solvents
• ISSN: 1001-604X; 1614-7065
• DOI: 10.1002/cjoc.202300725

Comprehensive Summary The development of switchable solvent‐free multicomponent reactions to build high‐value‐added products is an important demand for organic synthesis. Herein, we detailed the successful implementation of a switchable strategy for the construction of diverse 4‐fluoroalkyl‐1,4‐dihydropyrimidines and 4‐fluoroalkyl‐pyrimidines via a solvent/additive‐free [3 + 2 + 1] annulation, starting from readily available enamines, trifluoroacetaldehyde hydrate or 1‐ethoxy‐2,2‐difluoroethanol and amidines hydrochloride. This reaction conforms to the concept of green synthesis, and provides a new avenue to access valuable fluorinated heterocycles. A switchable strategy for the construction of diverse 4‐fluoroalkyl‐1,4‐dihydropyrimidines and 4‐fluoroalkyl‐pyrimidines via a solvent/additive‐free [3 + 2 + 1] annulation, starting from readily available enamines, trifluoroacetaldehyde hydrate or 1‐ethoxy‐2,2‐difluoroethanol and amidines hydrochloride has been developed.