Synthesis Of Pyrimidinone Derivatives Research Articles

ChemInform Abstract: Broensted Acidic Ionic Liquid as an Efficient and Reusable Catalyst for One‐Pot, Three‐Component Synthesis of Pyrimidinone Derivatives via Biginelli‐Type Reaction under Solvent‐Free Conditions.

AbstractThe first report on the use of a Broensted acidic ionic liquid for the synthesis of pyrimidine derivatives (IV) (20 examples) via a Biginelli‐type reaction is given.

An efficient and environmentally friendly procedure for synthesis of pyrimidinone derivatives by use of a Biginelli-type reaction

A Biginelli-type three-component reaction involving cyclopentanone, aromatic aldehyde, and urea or thiourea for preparation of pyrimidinone derivatives under neat conditions is described. This condensation reaction can also take place smoothly in the presence of vitamin B1 in EtOH at 80 °C in good yield. The procedure is simple, high-yielding, time-saving, and environment friendly.

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).

Tandem sigmatropic shifts in [4 + 2] cycloaddition reactions of 1,3-diazabuta-1,3-dienes with butadienylketene: synthesis of pyrimidinone derivatives

The reactions of 4-dialkylamino substituted 1,3-diazabuta-1,3-dienes 1 with butadienylketene 2, are shown to undergo [4 + 2] cycloadditions to yield 5-(buta-1′,3′-dienyl)pyrimidinone 4 and tandem [1,5]H and [1,5]SCH3 shifts are shown to accompany the [4 + 2] cycloaddition reactions of 4-dialkylamino-4-methylthio substituted 1,3-diazabuta-1,3-dienes 5 with 2. The regioselective reactions of N-arylamino-1,3-diazabuta-1,3-dienes 11 and 14 with butadienylketene 2 are reported to yield 5-(buta-1′,3′-dienyl)-2-dialkylaminopyrimidin-4(3H)-one 13 and a mixture of 5-(buta-1′,3′-dienyl)-2-methylthiopyrimidin-4(3H)-one 17, 2-methylthio-5-[1′-(N-phenylamino)but-2′-enyl]pyrimidin-4(3H)-one 19 and 2-methylthio-5-[3′-(N-phenylamino)but-1′-enyl]pyrimidin-4(3H)-one 20, respectively. Tandem [1,5]H, [1,3]NHPh and [1,5]NHPh shifts are involved in the formation of pyrimidinones 19 and 20. The Diels–Alder reactions of the 5-dienylpyrimidinones with dimethyl acetylenedicarboxylate (DMAD) and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) yielded corresponding cycloadducts.