Efficient and Facile Synthesis of 2,4-Diamino-6-arylpyrimidine-5-carbonitrile Under Solvent-Free Conditions

REFERENCES

• Ju , Y. H. ; Varma , R. S. Microwave-assisted cyclocondensation of hydrazine derivatives with alkyl dihalides or ditosylates in aqueous media: Syntheses of pyrazole, pyrazolidine, and phthalazine derivatives . Tetrahedron Lett. 2005 , 46 , 6011 – 6014 .
   Web of Science ®Google Scholar
• Noga , E. J. ; Barthalmus , G. T. ; Mitchell , M. K. Cyclic amines are selective cytotoxic agents for pigmented cells . Cell Biol. Int. Rep. 1986 , 10 , 239 – 247 .
   PubMedGoogle Scholar
• Luzzio , F. A. ; Wlodarczyk , M. T. Preparation of benzoheterocyclic carbaldeydes . Tetrahedron Lett. 2009 , 50 , 580 – 583 .
   Web of Science ®Google Scholar
• Gomez-Contreras , F. ; Navarro , P. Diazapolycyclic compounds, XVI: NMR stereochemical studies on the acid-catalyzed oxirane ring-opening reactions of unsubstituted, 2-methyl- and 2,3-dimethyl-substituted-2,3-epoxy-4a,12a-diaza-1,2,3,4,4a,5,12,12a-octahydronaphthacene-5,12-diones. J. Heterocycl. Chem. 1979, 16, 1035–1040.
   Web of Science ®Google Scholar
• Herav , M. M. ; Baghernejad , B. ; Oskooie , H. A. A novel three-component reaction for the synthesis of N-cyclohexyl-3-aryl-quinoxaline-2-amines . Tetrahedron Lett. 2009 , 50 , 767 – 769 .
   Web of Science ®Google Scholar
• Madapa , S. ; Tusi , Z. ; Mishra , A. ; Srivastava , K. ; Pandey , S. K. ; Tripathi , R. ; Puri , S. K. ; Batra , S. Search for new pharmacophores for antimalarial activity, part II: Synthesis and antimalarial activity of new 6-ureido-4-anilinoquinazolines . Bioorg. Med. Chem. 2009 , 17 , 222 – 234 .
   PubMed Web of Science ®Google Scholar
• Fujiwara , N. ; Nakajima , T. ; Ueda , Y. ; Fujita , H. ; Kawakami , H. Novel piperidinylpyrimidine derivatives as inhibitors of HIV-1 LTR activation . Bioorg. Med. Chem. 2008 , 16 , 9804 – 9816 .
   PubMed Web of Science ®Google Scholar
• Gomez-Contreras , F. ; Lora-Tamayo , M. ; Navarro , P. ; Pardo , M. Diazapolycyclic compounds—XIV: Epoxides from diazaquinone adducts: Synthesis and stereochemical characterization . Tetrahedron 1978 , 34 , 3499 – 3504 .
   Web of Science ®Google Scholar
• Eberbach , W. ; Fritz , H. ; Labe , N. A simple route to furo[3,4-b]furans, compounds with a new diheteropentalene system . Angew. Chem., Int. Ed. 1998 , 27 , 568 – 569 .
   Web of Science ®Google Scholar
• Munro-Leighton , C. ; Delp , S. A. ; Alsop , N. M. ; Blue , E. D. T. ; Gunnoe , B. Anti-Markovnikov hydroamination and hydrothiolation of electron-deficient vinylarenes catalyzed by well-defined monomeric copper(I) amido and thiolate complexes . Chem. Commun. 2008 , 111 – 113 .
   PubMed Web of Science ®Google Scholar
• Azas , N. ; Rathelot , P. ; Djekou , S. ; Delmas , F. ; Gellis , A. ; Di Giorgio , C. ; Vanelle , P. ; Timon-David , P. Antiparasitic activity of highly conjugated pyrimidine-2,4-dione derivatives . Farmaco 2003 , 58 , 1263 – 1270 .
   PubMedGoogle Scholar
• Agarwal , A. ; Srivastava , K. ; Puri , S. K. ; Chauhan , P. M. S. Synthesis of 2,4,6-trisubstituted pyrimidines as antimalarial agents . Bioorg. Med. Chem. 2005 , 13 , 4645 – 4650 .
   PubMed Web of Science ®Google Scholar
• Johar , M. ; Manning , T. ; Kunimoto , D. Y. ; Kumar , R. Synthesis and in vitro anti-mycobacterial activity of 5-substituted pyrimidine nucleosides . Bioorg. Med. Chem. 2005 , 13 , 6663 – 6671 .
   PubMed Web of Science ®Google Scholar
• (a) Gompper , R. ; Mair , H.-J. ; Polborn , K. Synthesis of oligo(diazaphenyls): Tailor-made fluorescent heteroaromatics and pathways to nanostructures . Synthesis 1997 , 696 – 718 ; (b) Kanbara , T. ; Kushida , T. ; Saito , N. ; Kuwajima , I. ; Kubota , K. ; Yamamoto , T. Preparation and properties of highly electron-accepting poly(pyrimidine-2,5-diyl) . Chem. Lett. 1992 , 583 – 584 .
   Web of Science ®Google Scholar
• (a) Hanan , G. S. ; Vilkmer , D. ; Schubert , U. S. ; Lehn , J.-M. ; Baum , G. ; Fenske , D. Coordination arrays: Tetranuclear cobalt(II) complexes with [2 × 2]-grid structure . Angew. Chem., Int. Ed. 1997 , 36 , 1842 – 1844 ; (b) Bassani , D. M. ; Lehn , J.-M. ; Baum , G. ; Fenske , D. Designed self-generation of an extended helical structure from an achiral polyheterocylic strand . Angew. Chem., Int. Ed. 1997 , 36 , 1845 – 1847 .
   Web of Science ®Google Scholar
• Wong , K. T. ; Hung , T.-S. ; Lin , Y. ; Wu , C.-C. ; Lee , G.-H. ; Peng , S.-M. ; Chou , C. H. ; Su , Y. O. Suzuki coupling approach for the synthesis of phenylene-pyrimidine alternating oligomers for blue light-emitting material . Org. Lett. 2002 , 4 , 513 – 516 .
   PubMed Web of Science ®Google Scholar
• (a) Harriman , A. ; Ziessel , R. Building photoactive molecular-scale wires . Coord. Chem. Rev. 1998 , 171 , 331 – 339 ; (b) Harriman , A. ; Ziessel , R. Making photoactive molecular-scale wires . Chem. Commun. 1996 , 1707 – 1716 .
   Web of Science ®Google Scholar
• (a) Tanaka , T. ; Toda , F. Solvent-free organic synthesis . Chem. Rev. 2000 , 100 , 1025 – 1074 ; (b) Cave , G. W. V. ; Raston , C. L. Toward benign syntheses of pyridines involving sequential solvent free aldol and Michael addition reactions . Chem. Commun. 2000 , 2199 – 2200 ; (c) Babak Kaboudin , B. ; Karimi , M. A new, efficient, and simple method for the one-pot synthesis of a-acetoxyphosphonates from aldehydes under solvent-free conditions . Bioorg. Med. Chem. Lett. 2006 , 16 , 5324 – 5327 ; (d) Liang , B. ; Wang , X. T. ; Wang , J. X. ; Du , Z. Y. New three-component cyclocondensation reaction: Microwave-assisted one-pot synthesis of 5-unsubstituted-3,4-dihydropyrimidin-2(1H)-ones under solvent-free conditions . Tetrahedron , 2007 , 63 , 1981 – 1986 .
   PubMed Web of Science ®Google Scholar
• (a) Rong , L. C. ; Han , H. X. ; Wang , S. H. ; Zhuang , Q. Y. Efficient synthesis of polysubstituted pyridine under solvent-free conditions without using any catalysts . Synth. Commun. 2008 , 38 , 1808 – 1814 ; (b) Rong , L. C. ; Wang , H. Y. ; Shi , J. W. ; Yang , F. ; Yao , H. ; Tu , S. J. ; Shi , D. Q. An efficient and facile procedure for the synthesis of 4,6-diaryl-2(1H)-pyridones under solvent-free conditions . J. Heterocycl. Chem. 2007 , 44 , 1505 – 1508 ; (c) Rong , L. C. ; Han , H. X. ; Jiang , H. ; Tu , S. J. Efficient NaOH-catalyzed reaction of aromatic aldehyde, cyclic ketones, and malononitrile under solvent-free conditions using a grinding method . Synth. Commun. 2008 , 38 , 3030 – 3842 .
   Web of Science ®Google Scholar