A Simple and efficient Synthesis of 3,4-Dihydropyrimidin-2-Ones catalysed by Amidosulfonic Acid †

A general and practical route for the synthesis of dihydropyrimidines by the one-pot cyclocondensation of aldehydes, β-ketoesters and urea is described using NH2SO3H as catalyst. Yields and selectivities are significantly better than under classical Biginelli reaction conditions.

[1]  S. Carloni,et al.  A revision of the Biginelli reaction under solid acid catalysis. Solvent-free synthesis of dihydropyrimidines over montmorillonite KSF , 1999 .

[2]  E. Hu,et al.  Unprecedented Catalytic Three Component One-Pot Condensation Reaction: An Efficient Synthesis of 5-Alkoxycarbonyl- 4-aryl-3,4-dihydropyrimidin-2(1H)-ones , 1998 .

[3]  C. Kappe.  A Reexamination of the Mechanism of the Biginelli Dihydropyrimidine Synthesis. Support for an N-Acyliminium Ion Intermediate(1). , 1997, The Journal of organic chemistry.

[4]  P. Wipf,et al.  Fluorous Synthesis: Fluorous Protocols for the Ugi and Biginelli Multicomponent Condensations. , 1997, The Journal of organic chemistry.

[5]  C. Kappe,et al.  Conformational analysis of 4-aryl-dihydropyrimidine calcium channel modulators. A comparison of ab initio, semiempirical and X-ray crystallographic studies , 1997 .

[6]  P. Wipf,et al.  Fluorous Synthesis: A Fluorous-Phase Strategy for Improving Separation Efficiency in Organic Synthesis , 1997, Science.

[7]  Graz,et al.  SYNTHESIS AND AROMATIZATION OF DIHYDROPYRIMIDINES STRUCTURALLY RELATED TO CALCIUM CHANNEL MODULATORS OF THE NIFEDIPINE-TYPE , 1997 .

[8]  P. Wipf,et al.  A SOLID PHASE PROTOCOL OF THE BIGINELLI DIHYDROPYRIMIDINE SYNTHESIS SUITABLE FOR COMBINATORIAL CHEMISTRY , 1995 .

[9]  C. Kappe.  100 years of the biginelli dihydropyrimidine synthesis , 1993 .

[10]  S. Moreland,et al.  Dihydropyrimidine calcium channel blockers. 4. Basic 3-substituted-4-aryl-1,4-dihydropyrimidine-5-carboxylic acid esters. Potent antihypertensive agents. , 1992, Journal of medicinal chemistry.

[11]  A Hedberg,et al.  Dihydropyrimidine calcium channel blockers. 3. 3-Carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid esters as orally effective antihypertensive agents. , 1991, Journal of medicinal chemistry.

[12]  G. Rovnyak,et al.  Substituted 1,4-dihydropyrimidines. 3. Synthesis of selectively functionalized 2-hetero-1,4-dihydropyrimidines , 1989 .

[13]  K. Atwal,et al.  Synthesis of substituted 1,2,3,4-tetrahydro-6-methyl-2-oxo-5-pyrimidinecarboxylic acid esters: the Biginelli condensation revisited , 1987 .

[14]  M. Malley,et al.  Synthesis of substituted 1,2,3,4-tetrahydro-6-methyl-2-thioxo-5-pyrimidinecarboxylic acid esters , 1987 .

[15]  K. Folkers,et al.  Researches on Pyrimidines. CXXXIII. Some Reactions and Derivatives of 2-Keto-4-phenyl-5-carbethoxy-6-methyl-1,2,3,4-tetrahydropyrimidine , 1933 .

[16]  H. Harwood,et al.  RESEARCHES ON PYRIMIDINES. CXXX. SYNTHESIS OF 2-KETO-1,2,3,4-TETRAHYDROPYRIMIDINES , 1932 .