One‐Pot Synthesis of 4,6‐Diaryl‐2‐oxo‐1,2‐dihydropyridine‐3‐carbonitriles via Three‐Component Cyclocondensation under Solvent‐Free Conditions

References

• Anastas , P. and Williamson , T. 1998 . Green Chemistry: Frontiers in Benign Chemical Synthesis and Procedures London : Oxford Science Publications .
   Google Scholar
• Cave , G. W. V. , Raston , C. L. and Scott , J. L. 2001 . Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility . Chem. Commun. , : 2159
   PubMed Web of Science ®Google Scholar
• Sheldon , R. A. 1997 . As estimated by determination of E‐factor . Chem. Ind. , : 12
   Google Scholar
• Montgomery , J. 2000 . Nickel-catalysted cyclizations, couplings, and cycloadditions involving three reactive components . Acc. Chem. Res. , 33 : 467
   PubMed Web of Science ®Google Scholar
• Sabitha , G. , Kiran Kumar Reddy , G. S. , Rsddy , K. B. and Yadav , J. S. 2003 . Vanadium (III) chloride catalyzed biginelli condensation:solution phase library generation of dihydropyrimidin-(2H)-ones . Tetrahedron Lett. , 44 : 6497
   Web of Science ®Google Scholar
• Labrie , P. 2003 . NiCl2 and NiCl2=6H2O: A very useful mild lewis acid in organic synthesis . Synlett , : 279
   Web of Science ®Google Scholar
• Varala , R. , Alam , M. M. and Adapa , S. R. 2003 . Bismuth triflate catalyzed one-pot synthesis of 3.4-dihydropyrimidin-2(1H)-ones: an improced protocol for the biginelli reaction . Synlett , : 67
   Google Scholar
• Dondoni , A. , Massi , A. , Minghini , E. , Sabbatini , S. and Bertolasi , V. 2003 . Model studies toward the synthesis of dihydropyrimidinyl and pyridyl-amino acids via three-component biginelli and hantzsch cyclocondensations . J. Org. Chem. , 68 : 6172
   PubMed Web of Science ®Google Scholar
• Hanselmann , R. , Zhou , J. C. , Ma , P. and Confalone , P. N. 2003 . Synthesis of cyclic and acyclic-amino acids via chelation-controlled 1,3-dipolar cycloaddition . J. Org. Chem. , 68 : 8739
   PubMed Web of Science ®Google Scholar
• Nair , V. , Mathai , S. and Varma , R. L. 2004 . The three-component reaction of dicarbomethoxycarbene, aldehydes, and nitrostyrenes: a stereoselective synthesis of substituted tetrahydrofurans . J. Org. Chem. , 69 : 1413
   PubMed Web of Science ®Google Scholar
• Gao , X. and Hall , D. G. H. 2003 . 3-Boronoacrolein as an exceptional heterodiene in the highly enantio- and diastereoselective Cr(III)-catalyzed three-component [4+2]/allylboration . J. Am. Chem. Soc. , 125 : 9308
   PubMed Web of Science ®Google Scholar
• Tanaka , T. and Toda , F. 2000 . Solvent-free organic synthesis . Chem. Rev. , 100 : 1025
   PubMed Web of Science ®Google Scholar
• Cave , G. W. V. and Raston , C. L. 2000 . Toward benign syntheses of pyridines involving sequential solvent free aldol and Michael addition reactions . J. Chem. Soc., Chem. Commun. , : 2199
   Google Scholar
• Shinobu , W. and Hitomi , S. 2003 . Calcite and fluorite as catalyst for the Knövenagel condensation of malononitrile and methyl cyanoacetate under solvent-free conditions . Tertahedron Lett. , 44 : 399
   Web of Science ®Google Scholar
• Liu , X. X. and Shen , Z. X. 2006 . Highly chemoselective synthesis of 1,2,3,4,5-pentasub-stituted cyclohexanols under solvent-free condition . Tetrahedron Lett. , 47 : 5623
   Web of Science ®Google Scholar
• Liu , W. Y. , Xu , Q. H. , Liang , Y. M. , Chen , B. H. , Liu , W. M. and Ma , Y. X. 2001 . Preparation of ferrocenyl mono-and dienone derivatives through aldol condensation of 1.1′-diacetylferrocene with aromatic aldehydes in dry conditions . J. Organom. Chem. , 637–639 : 719
   Web of Science ®Google Scholar
• Kaupp , G. , Naimi‐Jamal , M. R. and Schmeyers , J. 2003 . Solvent-free konenenagel condensations and michial additions in the solid state and in the melt with guantitative yield . Tetrahedron , 59 : 3753
   Web of Science ®Google Scholar
• Zolfigol , M. A. and Safaiee , M. 2004 . Synthesis of 1,4-dihydropyridines under solvent-free conditions . Synth. Lett. , 5 : 827
   Google Scholar
• Shaabani , A. , Bazgir , A. and Teimour , F. 2003 . Ammonium chloride-catalyzed one-pot synthesis of 3.4-dihydropynidin-2(1H)-ones under solvent conditions . Tetrahedron Lett. , 44 : 857
   Web of Science ®Google Scholar
• Jones , T. H. and Blum , M. S. 1983 . Alkaloids: Chemical and Biological Perspectives Edited by: Pelletier , S. W. Vol. 1 , 33 New York : Wiley .
   Google Scholar
• Fodor , G. B. and Colasanti , B. 1985 . Alkaloids: Chemical and Biological Perspectives Edited by: Pelletier , S. W. Vol. 3 , 1 New York : Wiley .
   Google Scholar
• Strunz , G. M. and Findlay , J. A. 1985 . The Alkaloids Edited by: Brossi , A. Vol. 26 , 89 Orlando : Academic Press .
   Google Scholar
• Daly , J. W. J. 1998 . Nat. Prod. , 61 : 162
   PubMed Web of Science ®Google Scholar
• Plunkett , A. O. 1994 . Pyrrole, pyrrolidine, pyridine, piperidine, and azepine alkaloids . Nat. Prod. Rep. , 11 : 581
   PubMed Web of Science ®Google Scholar
• Balasubramanian , M. and Keay , J. G. 1996 . Comprehensive Heterocyclic Chemistry II Edited by: Katritzky , A. R. , Rees , C. W. and Scriven , E. F. V. Vol. 5 , 245 Pergamon Press .
   Google Scholar
• Rubiralta , M. , Giralt , E. and Diez , A. 1991 . Piperidine: Structure, Preparation, Reactivity, and Synthetic Applications of Piperidine and Its Derivatives Amsterdam : Elsevier .
   Google Scholar
• Freeman , F. 1969 . Chemistry of malononitrile . Chem. Rev. , 5 : 591
   Web of Science ®Google Scholar
• Rastogi , R. R. , Kumar , A. , Ila , H. and Junjappa , H. 1978 . Reaction of -oxo- and -cyano-ketene SS-acetals with cyanoacetamide: a new general method for substituted and fused 4-alkylthio-3-cyano-2(1H)-pyridones and formation of novel pyridones through base-induced rearrangements . J. Chem. Soc., Perkins Trans. 1 , 6 : 549
   Google Scholar
• Otto , H. H. and Schmelz , H. 1982 . Reactions of (hydroxymethylene)tetralone with derivatives of cyanoacetic acid . Arch. Pharm. , 315 : 526
   Web of Science ®Google Scholar
• Aggarwal , V. , Singh , G. , Ila , H. and Junjappa , H. 1982 . Reaction of α-ketoketene S,N-acetals with cyanoacetamide: A new general method for substituted and fused 4-(N-alkylamino-, N-arylamino-, or N-morpholino)-3-cyano-2(1H)-pyridones . Synthesis , : 214
   Web of Science ®Google Scholar
• Alberola , A. , Andrés , C. , González‐Ortega , A. , Pedrosa , R. and Vicente , M. 1987 . The reaction of β-aminoenones with substituted acetonitriles. regiospecific synthesis of 2(1H)-pyridones . J. Heterocycl. Chem. , 24 : 709
   Web of Science ®Google Scholar
• Purkayastha , M. L. , Bhat , L. , Ila , H. and Junjappa , H. 1995 . 4-Alkoxy-3-cyano-2(1H)-pyridones and 5-alkoxyisoxazoles and their aryl substituted and snnulated derivatives from acylketene O,S-acetals . Synthesis , : 641
   Web of Science ®Google Scholar
• Krstic , V. , Misic‐Vukovic , M. and Radojkovic‐Velickovic , M. 1991 . Synthesis and identification of isomeric 4(6)-methyl-6(4)-(substituted phenyl)-3-cyano-2-pyridones . J. Chem. Res. Syno. , : 82
   Web of Science ®Google Scholar
• Lorente , A. , Cosme , A. , Coronada , P. and Soto , J. L. 1988 . Synthesis of 4,6-diaryl-2-cyanoimin- opiperidines from N-cyanocinnamamidines . Synthesis , : 739
   Google Scholar
• Rastogi , R. R. , Kumar , A. , Iia , H. and Junjappa , H. 1978 . Reaction of α-oxoketene SS-acetals with N-alkylcyanoacetamides: a new general method for substituted and fused 2,7-dialkyl-8-amino-5-cyano-2,7-naphth- yridine-1,6(2H,7H)-diones . J. Chem. Soc. Perkin Trans. 1 , : 554
   Google Scholar
• Alberola , A. , Calvo , L. A. , Ortega , A. J. , Rurz , M. C. S. and Yustos , Pedro . 1999 . Regioselective synthesis of 2(1H)-pyridinones from β-aminoenones and malononitrile. reaction mechanism . J. Org. Chem. , 64 : 9493
   Web of Science ®Google Scholar
• Li , W. W. , Chen , Y. and Lam , Y. L. 2004 . A facile solid-phase synthesis of 3,4,6-trisubstituted-2-pyridones using sodium benzenesulfinate as a traceless linker . Tetrahedron Lett. , 45 : 6545
   Web of Science ®Google Scholar
• Dave , C. G. , Shah , D. A. and Agrawal , Y. K. 2004 . A simple and convenient synthesis of 4,6-disubstituted-3-cyanopyridin-2(1H)-ones under solvent-free microwave conditions . Indian J. Chem., Sec. B , 43B : 885
   Google Scholar
• Kandeel , K. A. , Vernon , J. M. , Dransfield , T. A. , Fouli , F. A. and Youssef , A. S. A. 1990 . Reactions of malononitrile with acetylenic esters and ketones . J. Chem. Res. Syno. , : 276
   Web of Science ®Google Scholar
• Soto , J. L. , Seoane , C. and Mansilla , A. M. 1981 . A simple one-step synthesis of 2-pyridones from benzylidenacetophenones . Org. Prep. Proced. Int. , 13 : 331
   Web of Science ®Google Scholar
• Kuthan , J. , Nesv‐adba , P. , Popl , M. and Fahnrich , J. 1979 . Some 3-cyano-4,6-diaryl- 2-pyridones with luminescent properties . Coll. Czech. Chem. Commun. , 44 : 2409
   Google Scholar
• Kambe , S. , Saito , K. , Sakurai , A. and Hayashi , T. 1977 . A convenient method for the preparation of 2-pyridone derivatives . Synthesis , : 841
   Web of Science ®Google Scholar
• Rong , L. C. , Li , X. Y. , Wang , H. Y. , Shi , D. Q. and Tu , S. 2006 . An efficient and facile synthesis of 2-amino-4,6-diarylbenzene-1,3-dicarbonitrile and 1,2-dihydro-2-oxo-4,6-diarylpyridine-3-carbonitrile under solvent-free conditions . Chem. Lett. , 10 : 1314
   Web of Science ®Google Scholar
• Rong , L. C. , Li , X. Y. , Wang , H. Y. , Shi , D. Q. , Tu , S. J. and Zhuang , Q. Y. 2006 . Efficient synthesis of tetrahydrobenzo[b] pyrans under solvent-free conditions at room temperature . Synth. Commun. , 36 : 2363
   Web of Science ®Google Scholar
• Rong , L. C. , Li , X. Y. , Wang , H. Y. , Shi , D. Q. , Tu , S. J. and Zhuang , Q. Y. 2006 . Efficient green procedure for the Knoevenagel Condensation under solvent-free conditions . Synth. Commun. , 36 : 2407
   Web of Science ®Google Scholar
• Rong , L. C. , Li , X. Y. , Yao , C. S. , Wang , H. Y. and Shi , D. Q. 2006 . 2-[1-(3,4-Dichlorophenyl)-3-oxo-3-phenylpropyl]-3,4-dihydro-2H-naphthalen-1-one . Acta Crys. , E62 : o35
   Google Scholar
• Rong , L. C. , Li , X. Y. , Wang , H. Y. , Yao , C. S. and Shi , D. Q. 2006 . 2-Amino-5,6,7,8-tetrahydro-4-p-tolylnaphthalene-1,3-dicarbonitrile . Acta Crys. , E62 : o3004
   Google Scholar