One-Pot Synthesis of 4-Aminoquinazolines by Hexamethyldisilazane-Mediated Reaction of Quinazolin-4(3H)-ones with Amines

REFERENCES

• Hori , M. ; Iemura , R. ; Hara , H. ; Ozaki , A. ; Sukamoto , T. ; Ohtaka , H. Novel 4-phenoxy-2-(1-piperazinyl)quinazolines as potent anticonvulsive and antihypoxic agents . Chem. Pharm. Bull. 1990 , 38 , 681 .
   PubMed Web of Science ®Google Scholar
• Havera , H. J. ; Vidrio , H. J. Derivatives of 1,3-disubstituted 2,4(1H,3H)-quinazolinediones as possible peripheral vasodilators or antihypertensive agents . J. Med. Chem. 1979 , 22 , 1548 .
   PubMed Web of Science ®Google Scholar
• Chao , Q. ; Deng , L. ; Shih , H. ; Leoni , L. M. ; Genini , D. ; Carson , D. A. ; Cottam , H. B. Substituted isoquinolines and quinazolines as potential antiinflammatory agents: Synthesis and biological evaluation of inhibitors of tumor necrosis factor α . J. Med. Chem. 1999 , 42 , 3860 .
   PubMed Web of Science ®Google Scholar
• Kung , P. P. ; Casper , M. D. ; Cook , K. L. ; Wilson-Lingardo , L. ; Risen , L. M. ; Vickers , T. A. ; Ranken , R. ; Blyn , L. B. ; Wyatt , J. R. ; Cook , P. D. ; Ecker , D. J. Structure–activity relationships of novel 2-substituted quinazoline antibacterial agents. J. Med. Chem. 1999, 42, 4705.
   PubMed Web of Science ®Google Scholar
• Liverton , N. J. ; Armstrong , D. J. ; Claremon , D. A. ; Remy , D. C. ; Bardwin , J. J. ; Lynch , R. J. ; Zhang , G. ; Gould , R. J. Nonpeptide glycoprotein IIb/IIIa inhibitors: Substituted quinazolinediones and quinazolinones as potent fibrinogen receptor antagonists . Bioorg. Med. Chem. Lett. 1998 , 8 , 483 .
   PubMed Web of Science ®Google Scholar
• Brunton , S. A. ; Stibbard , J. H. A. ; Rubin , L. L. ; Kruse , L. I. ; Guicherit , O. M. ; Boyd , E. A. ; Price , S. Potent inhibitors of the hedgehog signaling pathway . J. Med. Chem. 2008 , 51 , 1108 .
   PubMed Web of Science ®Google Scholar
• Li , J. J. ; Nahra , J. ; Johnson , A. R. ; Bunker , A. ; O'Brien , P. ; Yue , W. S. ; Ortwine , D. F. ; Man , C. F. ; Baragi , V. ; Kilgore , K. ; Dyer , R. D. ; Han , H. K. Quinazolinones and pyrido[3,4-d]pyrimidin-4-ones as orally active and specific matrix metalloproteinase-13 inhibitors for the treatment of osteoarthritis . J. Med. Chem. 2008 , 51 , 835 .
   PubMed Web of Science ®Google Scholar
• Liu , L. T. ; Yuan , T. T. ; Liu , H. H. ; Chena , S. F. ; Wub , Y. T. Synthesis and biological evaluation of substituted 6-alkynyl-4-anilinoquinazoline derivatives as potent EGFR inhibitors . Bioorg. Med. Chem. Lett. 2007 , 17 , 6373 .
   PubMed Web of Science ®Google Scholar
• Mortlock , A. A. ; Foote , K. M. ; Heron , N. M. ; Jung , F. H. ; Pasquet , G. ; Lohmann , J. J. M. ; Warin , N. ; Renaud , F. ; De Savi , C. ; Roberts , N. J. ; Johnson , T. ; Dousson , C. B. ; Hill , G. B. ; Perkins , D. ; Hatter , G. ; Wilkinson , R. W. ; Wedge , S. R. ; Heaton , S. P. ; Odedra , R. ; Keen , N. J. ; Crafter , C. ; Brown , E. ; Thompson , K. ; Brightwell , S. ; Khatri , L. ; Brady , M. C. ; Kearney , S. ; McKillop , D. ; Rhead , S. ; Parry , T. ; Green , S. Discovery, synthesis, and in vivo activity of a new class of pyrazoloquinazolines as selective inhibitors of Aurora B kinase . J. Med. Chem. 2007 , 50 , 2213 .
   PubMed Web of Science ®Google Scholar
• Rewcastle , G. W. ; Palmer , B. D. ; Bridges , A. J. ; Showalter , H. D. H. ; Sun , L. ; Nelson , J. ; McMichael , A. ; Kraker , A. J. ; Fry , D. W. ; Denny , W. A. Tyrosine kinase inhibitors, 9: Synthesis and evaluation of fused tricyclic quinazoline analogues as ATP site inhibitors of the tyrosine kinase activity of the epidermal growth factor receptor . J. Med. Chem. 1996 , 39 , 918 .
   PubMed Web of Science ®Google Scholar
• Barlaam , B. ; Ballard , P. ; Bradbury , R. H. ; Ducray , R. ; Germain , H. ; Hickinson , D. M. ; Hudson , K. ; Kettle , J. G. ; Klinowska , T. ; Magnien , F. ; Ogilvie , D. J. ; Olivier , A. ; Pearson , S. E. ; Scott , J. S. ; Suleman , A. ; Trigwell , C. B. ; Vautier , M. ; Whittaker , R. D. ; Wood , R. A new series of neutral 5-substituted 4-anilinoquinazolines as potent, orally active inhibitors of erbB2 receptor tyrosine kinase . Bioorg. Med. Chem. Lett. 2008 , 18 , 674 .
   PubMed Web of Science ®Google Scholar
• Luth , A. ; Lowe , W. Syntheses of 4-(indole-3-yl)quinazolinese—A new class of epidermal growth factor receptor tyrosine kinase inhibitors . Eur. J. Med. Chem. 2008 , 43 , 1478 .
   PubMed Web of Science ®Google Scholar
• Barker , A. J. ; Gibson , K. H. ; Grundy , W. ; Godfrey , A. A. ; Barlow , J. J. ; Healy , M. P. ; Woodburn , J. R. ; Ashton , S. E. ; Curry , B. J. ; Scarlett , L. ; Henthorn , L. ; Richards , L. Studies leading to the identification of ZD1839 (Iressa™): An orally active, selective epidermal growth factor receptor tyrosine kinase inhibitor targeted to the treatment of cancer . Bioorg. Med. Chem. Lett. 2001 , 11 , 1911 .
   PubMed Web of Science ®Google Scholar
• Zhang , Y. D. ; Xu , C. L. ; Houghten , R. A. ; Yu , Y. P. Scaffold approach for solid-phase synthesis of 2,3-disubstituted 8-arylamino-3H-imidazo[4,5-g]quinazolines . J. Comb. Chem. 2007 , 9 , 9 .
   PubMedGoogle Scholar
• Wan , Z. K. ; Wacharasindhu , S. ; Binnun , E. ; Mansour , T. An efficient direct amination of cyclic amides and cyclic ureas . Org. Lett. 2006 , 8 , 2425 .
   PubMed Web of Science ®Google Scholar
• Wan , Z. K. ; Wacharasindhu , S. ; Levins , C. G. ; Lin , M. ; Tabei , K. ; Mansour , T. S. The scope and mechanism of phosphonium-mediated SNAr reactions in heterocyclic amides and ureas . J. Org. Chem. 2007 , 72 , 10194 .
   PubMed Web of Science ®Google Scholar
• Singer , R. A. ; Dore , M. Practical amination of nitropyridones by silylation. Org. Process Res. Dev. 2008, 12, 1261.
   Google Scholar
• Vorbruggen , H. Simple amination of aromatic hydroxy-nitrogen heterocycles . Angew. Chem., Int. Ed. Engl. 1972 , 11 , 305 .
   Google Scholar
• Vorbruggen , H. ; Krolikiewicz , K. Amination, III: Trimethylsilanol as leaving group, V: Silylation–amination of hydroxy N-heterocycles . Chem. Ber. 1984 , 117 , 1523 .
   Google Scholar
• Nishikawa , S. ; Kumazawa , Z. ; Kashimura , N. ; Maki , S. ; Nishikimi , Y. Sythesis and cytokinin activity of 4- and 2,4-substituted pyrido[3,4-d]pyrimidines . Agric. Biol Chem. 1986 , 50 , 495 .
   Google Scholar
• Mitidieri-Costanza , A. ; Sleiter , G. The reaction of 5-methyl-4-phenoxyquinazoline with piperidine in isooctane: Further evidence for steric inhibition of bifunctional catalysis . J. Prakt. Chem. 1985 , 327 , 865 .
   Google Scholar
• Gulevskaya , A. V. ; Maes , B. U. W. ; Meyers , C. ; Herrebout , W. A. ; van der Veken , B. J. C–N bond formation by the oxidative alkylamination of azines: Comparison of AgPy2MnO4 versus KMnO4 as oxidant . Eur. J. Org. Chem. 2006 , 5305 .
   Google Scholar
• Breza , N. ; Pato , J. ; Orfi , L. ; Hegymegi-Barakonyi , B. ; Banhegyi , P. ; Varkondi , E. ; Borbely , G. ; Petak , I. ; Keri , G. Synthesis and characterization of novel quinazoline type inhibitors for mutant and wild-type EGFR and RICK kinases . J. Recept. Sig. Transd. 2008 , 28 , 361 .
   Web of Science ®Google Scholar
• Hou , T. J. ; Zhu , L. L. ; Chen , L. R. ; Xu , X. J. Mapping the binding site of a large set of quinazoline type EGF-R inhibitors using molecular field analyses and molecular docking studies . J. Chem. Inf. Comput. Sci. 2003 , 43 , 273 .
   PubMedGoogle Scholar
• Kurteva , V. B. ; Zlatanova , V. N. ; Dimitrov , V. D. Solvent-free synthesis of a series of differently N-substituted 4-amino-2-methylquinazolines under microwave irradiation . Arkivoc 2006 , 1 , 46 .
   Google Scholar
• Lee , Y. B. ; Ahn , C. H. Quinazoline derivatives and therapeutic use thereof. U.S. Patent Appl. 0187231, 2007 .
   Google Scholar
• Shen , Z. L. ; Hong , Y. M. ; He , X. F. ; Mo , W. M. ; Hu , B. X. ; Sun , N. ; Hu , X. Q. Switching the chemoselectivity in the amination of 4-chloroquinazolines with aminopyrazoles . Org. Lett. 2010 , 12 , 552 .
   Google Scholar