A Facile Synthesis of Functionalized 1,2,6,7-Tetrahydroimidazo[1,5-c]pyrimidine-3,5-diones

REFERENCES

• Kinel , F. A. ; Romo , J. ; Rosenkrauz , G. ; Sondkeimer , F. The constituents of Casimiroa edulis llave et lex, part I: The seed . J. Chem. Soc. 1956 , 4163 – 4169 .
   Web of Science ®Google Scholar
• Sondheimer , F. ; Melera , A. ; Kincl , F. A. Generalized polymerization mechanism of multi-vinyl monomers: Bicyclo- and tricyclo-intramolecular propagation . J. Am. Chem. Soc. 1961 , 83 , 2022 – 2023 .
   Google Scholar
• Siddigi , S. M. ; Melman , N. ; Olah , M. E. ; Jain , R. ; Evans , R. ; Glashofer , M. ; Radget , W. ; Cohen , L. A. ; Daly , J. W. ; Stiles , G. L. ; Jacobson , U. A. Survey of nonxanthine derivatives as adenosine receptor ligands. Nucleosides Nucleotides 1996, 15, 693–717.
   Google Scholar
• Yoshida , O. ; Yasukata , T. ; Sumino , Y. ; Munekage , T. ; Narukawa , Y. ; Nishitani , Y. Novel semi-synthetic glycopeptide antibiotics active against methicillin-resistant staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE): Doubly-modified water-soluble derivatives of chloroorienticin B . Bioorg. Med. Chem. Lett. 2002 , 12 , 3027 – 3031 .
   PubMed Web of Science ®Google Scholar
• Arcari , G. ; Bernardi , L. ; Cimaschi , R. ; Falconi , G. ; Luini , F. ; Scarponi , U. Anti-ulcer and antisecretory activity of selected imidazopiperidines . Arz. Forsch. 1984 , 34 , 1467 – 1471 .
   Google Scholar
• Nordlander , E. ; Zhivich , A. B. ; Koldobskii , G. I. ; Dubinskii , M. Yu. Synthesis of 4-(2-bromoethyl)-1-methylimidazole . Russ. J. Org. Chem. 1996 , 32 , 1825 – 1826 .
   Google Scholar
• Narayanan , S. ; Vangapandu , S. ; Jain , R. Regiospecific synthesis of 2,3-disubstituted-histidines and histamines . Bioorg. Med. Chem. Lett. 1996 , 11 , 1133 – 1136 .
   Google Scholar
• Quattropani , A. ; Dorbais , J. ; Covini , D. ; Desforges , G. ; Rueckle , T. Thiazole derivatives and use thereof. WO Patent 2006/125805(A1), 2006; http://www.espacenet.com.
   Google Scholar
• Breitfelder , S. ; Maier , U. ; Hoenke , C. ; Joergensen , A. ; Pautsch , A. ; Brandl , T. ; Grauert , M. ; Hoffmann , M. ; Scheuerer , S. ; Erb , K. ; Pieper , M. ; Pragst , I. Thiazolyl-dihydro-cyclopentapyrazole. US Patent 2007/238730, 2007; http://www.espacenet.com.
   Google Scholar
• Brandl , T. ; Maier , U. ; Hoenke , C. ; Joergensen , A. T. ; Pautsch , A. ; Breitfelder , S. ; Grauert , M. ; Hoffmann , M. ; Scheuerer , S. ; Erb , K. ; Pieper , M. ; Pragst , I. Thiazolyl-dihydro-chinazoline. US Patent 2007/238746, 2007; http://www.espacenet.com.
   Google Scholar
• Maier , U. ; Grauert , M. ; Hoffmann , M. ; Hoenke , C. ; Joergensen , A. T. ; Pautsch , A. ; Brandl , T. ; Breitfelder , S. ; Scheuerer , S. ; Erb , K. ; Pieper , M. ; Pragst , I. Thiazolyl-dihydro-indazole. US Patent 2007/259855, 2007; http://www.espacenet.com.
   Google Scholar
• Borchers , A. ; Schunack , W. H2-Antihistaminika, 19: Mitt: Synthese und H2-antihistaminishe Wirkung N α -substituier Histamine . Arch. Pharm. 1984 , 317 , 455 – 459 .
   Google Scholar
• Jairam , R. ; Potvin , P. G. Zinc dication inclusion complexes of endodentate tripodands as carbonic anhydrase-inspired artitocial esterases . J. Org. Chem. 1992 , 57 , 4136 – 4141 .
   Web of Science ®Google Scholar
• Schlögl , W. ; Woidich , H. Uber die Cyclisierung von Histidinderivaten . Monatsh. Chem. 1956 , 87 , 679 – 694 .
   Google Scholar
• Chivikas , C. J. ; Hodres , J. C. Phenacyl-directed alkylation of imidazols: A new regiospecific synthesis of 3-substituted L-histidines . J. Org. Chem. 1987 , 52 , 3591 – 3954 .
   Web of Science ®Google Scholar
• Lebed' , P. S. ; Kos , P. O. ; Polovinko , V. V. ; Tolmachev , A. A. ; Vovk , M. V. Synthesis of new polyfunctional 5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidin-5-ones by the aza-Wittig reaction followed by intramolecular cyclization and 1,3-prototropic shift . Russ. J. Org. Chem. 2009 , 45 , 921 – 927 .
   Web of Science ®Google Scholar
• Saha , S. ; Seth , S. ; Moorthy , J. N. Functionalized praline with double hydrogen bounding potential: Highly enantioselective Michael addition of carbonyl compounds to β-nitrostyrene in brine . Tetrahedron Lett. 2010 , 51 , 5281 – 5286 .
   Web of Science ®Google Scholar
• Page , D. ; Nguyen , N. ; Bernard , S. ; Coupol , M. ; Cosselin , M. ; Lepage , J. ; Adam , L. ; Brown , W. New scaffolds in the development of Mu opioid-receptor ligands . Bioorg. Med. Chem. Lett. 2003 , 13 , 1585 – 1590 .
   PubMed Web of Science ®Google Scholar
• Choong , I. C. ; Lew , W. ; Lee , D. ; Phom , P. ; Burgett , M. N. ; Lom , J. W. ; Wiesmann , C. ; Luong , T. N. ; Fahr , B. ; Delan , W. L. ; McDowell , R. S. ; Allen , D. A. ; Erlanson , D. A. ; Gordon , E. M. ; O'Brien , T. Identification of potent and selective small-molecule inhibitors of caspase-3 through the use of extended tethering and structure-based drug design . J. Med. Chem. 2002 , 45 , 5005 – 5022 .
   PubMed Web of Science ®Google Scholar
• Maduskuie , T. P. Uracyl derivatives as inhibitors of TNF-alpha converting enzyme (TACE) and matrix methaloproteinases. US Patent 2003/229081(A1), 2003; http://www.espacenet.com.
   Google Scholar
• George , T. ; Tahilramani , R. ; Mehta , D. V. Condensed heterocycles from 5-ethoxycarbonyl-6-methyltetrahydropyrimidine-2-ones . Synthesis 1975 , 405 – 407 .
   Web of Science ®Google Scholar
• Cotarca , L. ; Delogu , P. ; Nardelli , A. ; Unji , V. Bis(trichloromethyl)carbonate in organic synthesis . Synthesis 1996 , 553 – 576 .
   Web of Science ®Google Scholar