Transition metal free synthesis of 2,4,6-trisubstituted pyrimidines via Cope-type hydroamination of 1,4-diarylbuta-1,3-diynes

We have developed an efficient and transition metal free methodology for the synthesis of 2,4,6-trisubstituted pyrimidines by the Cope-type hydroamination reaction of 1,4-diarylbuta-1,3-diynes with amidines in DMSO solvent.

[1]  J. Camp,et al.  Platinum-catalysed synthesis of trichloroamidines , 2013 .

[2]  J. Camp,et al.  Methods for the Direct Synthesis of Benzoxazoles from Halogenated Nitriles in Alcoholic Solvents , 2013 .

[3]  Jihui Li,et al.  Copper-catalyzed oxidative diamination of terminal alkynes by amidines: synthesis of 1,2,4-trisubstituted imidazoles. , 2013, Organic letters.

[4]  Xiaoqiang Yu,et al.  Synthesis of 3,5-disubstituted pyrazoles via Cope-type hydroamination of 1,3-dialkynes. , 2013, The Journal of organic chemistry.

[5]  B. Trofimov,et al.  A one-pot approach to Δ2-isoxazolines from ketones and arylacetylenes. , 2013, Organic letters.

[6]  H. Gérard,et al.  Stereoselective and catalytic access to β-enaminones: an entry to pyrimidines. , 2012, The Journal of organic chemistry.

[7]  Xiaoqiang Yu,et al.  Synthesis of 3,5-disubstituted isoxazoles via Cope-type hydroamination of 1,3-dialkynes. , 2012, Organic letters.

[8]  J. Lyssikatos,et al.  Access to Saturated Fused PyrimidineDerivatives via a Flexible N-Vinyl TertiaryEnamide Synthesis , 2011 .

[9]  P. Jessop,et al.  A synthesis of acetamidines. , 2011, The Journal of organic chemistry.

[10]  J. Camp,et al.  Synthesis of highly substituted pyrroles via nucleophilic catalysis. , 2010, The Journal of organic chemistry.

[11]  B. Trofimov,et al.  A domino reaction of alpha,beta-acetylenic gamma-hydroxy nitriles with arenecarboxylic acids: an unexpected facile shortcut to 4-cyano-3(2H)-furanones. , 2010, Organic letters.

[12]  M. D. Hill,et al.  Synthesis of densely substituted pyrimidine derivatives. , 2009, The Journal of organic chemistry.

[13]  T. Konakahara,et al.  An unprecedented approach to 4,5-disubstituted pyrimidine derivatives by a ZnCl(2)-catalyzed three-component coupling reaction. , 2009, Organic letters.

[14]  André M. Beauchemin,et al.  Intermolecular cope-type hydroamination of alkenes and alkynes. , 2008, Angewandte Chemie.

[15]  André M. Beauchemin,et al.  Intermolecular Cope-type hydroamination of alkynes using hydrazines. , 2008, Chemical communications.

[16]  M. D. Hill,et al.  Single-step synthesis of pyrimidine derivatives. , 2006, Journal of the American Chemical Society.

[17]  Rakesh Kumar,et al.  Synthesis and in vitro anti-mycobacterial activity of 5-substituted pyrimidine nucleosides. , 2005, Bioorganic & medicinal chemistry.

[18]  K. Srivastava,et al.  Synthesis of 2,4,6-trisubstituted pyrimidines as antimalarial agents. , 2005, Bioorganic & medicinal chemistry.

[19]  D. Yamazaki,et al.  Pyrimidine-core extended pi-systems: general synthesis and interesting fluorescent properties. , 2004, Journal of the American Chemical Society.

[20]  G. Clavier,et al.  A selective synthesis of 2-([2,2]paracyclophan-5-yl)pyrrole from 5-acetyl[2,2]paracyclophane via the Trofimov reaction , 2004 .

[21]  S. Peng,et al.  Suzuki coupling approach for the synthesis of phenylene-pyrimidine alternating oligomers for blue light-emitting material. , 2002, Organic letters.

[22]  P. Zhichkin,et al.  ChemInform Abstract: A General Procedure for the Synthesis of 2-Substituted Pyrimidine-5-carboxylic Esters. , 2002 .

[23]  J. G. Vries,et al.  Platinum catalysed hydrolytic amidation of unactivated nitriles , 2000 .

[24]  A. Harriman,et al.  Building photoactive molecular-scale wires , 1998 .

[25]  A. Harriman,et al.  Making photoactive molecular-scale wires , 1996 .

[26]  T. Culbertson Synthesis of 5,6-dihydroxy-2-phenyl-4-pyrimidinecarboxylic acid, methyl ester, a corrected structure , 1979 .