Three‐component one‐pot synthesis of pyrimidinone derivatives in fluorous media: Ytterbium bis(perfluorooctanesulfonyl)imide complex catalyzed Biginelli‐type reaction

Abstract

magnified image The condensation of aromatic aldehyde, cyclopentanone, and urea or thiourea in the presence of Ytterbium bis(perfluorooctanesulfonyl)imide complex in perfluorodecalin was used to synthesize a variety of benzylidene heterobicyclic pyrimidinones in excellent yields. J. Heterocyclic Chem., (2009).

A new paradigm for designing ring construction strategies for green organic synthesis: implications for the discovery of multicomponent reactions to build molecules containing a single ring

“…Scheme 10 shows the following literature examples of [3 + 2 + 1] cycloadditions following the traditional mapping (red structure shown in Fig. 9): Biginelli [163–165], Shaabani [166], Martins [167], Khodaei [168], Saxena [169], Zhu [170], Zhu [171], Organ [172], Mizar [173], Schmidt [174], Ramalingan [175], Kappe [176], Hulme [177], Tu [178], Matache [179], Zhang [180], Singh [181], Hong [182], Lei [183], Shaabani [184], Tu [185], Han [186], Fang [187], and Zeng [188]. Scheme 11 shows the following literature examples of [3 + 2 + 1] cycloadditions following novel mappings (blue structures shown in Fig.…”

Synthesis of Dihydropyrimidinones and Thiones by Multicomponent Reactions: Strategies Beyond the Classical Biginelli Reaction

“…Recently, the preparation of DHPMs of type 18 using the three-component reaction of aldehydes, cyclopentanone and ureas/thioureas was also reported to proceed in excellent selectivity and high yield under catalysis by an ytterbium Lewis acid. 34,35 A rather interesting extension of the three-component Biginelli-like reaction using cyclic ketones is the example of steroid 22 that contains a cyclohexanone moiety acting as a monocarbonyl substrate in the reaction with benzaldehyde and thiourea. The DHPMfunctionalized steroid analogue 23 was directly formed under acidic conditions (Scheme 9).…”