Efficient Synthesis of Bicyclo[3.3.1]nonane Systems via Tandem 1,3-Dinucleophilic Addition of 4-Hydroxy-2-quinolinones to Quinolinium Salts

REFERENCES

• Hajdok , S. ; Conrad , J. ; Leutbecher , H. ; Strobel , S. ; Schleid , T. ; Beifuss , U. The Laccase-catalyzed domino reaction between catechols and heterocyclic 1,3-dicarbonyls and the unambiguous structure elucidation of the products by NMR spectroscopy and x-ray crystal structure analysis . J. Org. Chem. 2009 , 74 , 7230 .
   PubMed Web of Science ®Google Scholar
• Arya , K. ; Agarwal , M. Microwave-prompted multigram synthesis, structural determination, and photo-antiproliferative activity of fluorinated 4-hydroxyquinolinones . Bioorg. Med. Chem. Lett. 2007 , 17 , 86 .
   PubMed Web of Science ®Google Scholar
• Mitscher , L. A. Bacterial topoisomerase inhibitors: Quinolone and pyridone antibacterial agents . Chem. Rev. 2005 , 105 , 559 .
   PubMed Web of Science ®Google Scholar
• Afonso , A. ; Weinstein , J. ; Gentles , M. J. Antiviral compounds and antihypertensive compounds. PCT Int. Appl. WO9204327, 1993 .
   Google Scholar
• Morsay , A. M. ; Lerson , P. D. 3′-(Arylmethyl)- and 3′-(aryloxy)-3-phenyl-4-hydroxyquinolin-2(1H)-ones: Orally active antagonists of the glycine site on the NMDA receptor . J. Med. Chem. 1994 , 37 , 1402 .
   PubMed Web of Science ®Google Scholar
• Freeman , G. A. ; Andrews , III , C. W. ; Hopkins , A. L. ; Lowell , G. S. ; Schaller , L. T. ; Cowan , J. R. ; Gonzales , S. S. ; Koszalka , G. W. ; Hazen , R. J. ; Boone , L. R. ; Ferris , R. G. ; Creech , K. L. ; Roberts , G. B. ; Short , S. A. ; Weaver , K. ; Reynolds , D. J. ; Milton , J. ; Ren , J. ; Stuart , D. I. ; Stammers , D. K. ; Chan , J. H. Design of non-nucleoside inhibitors of HIV-1 reverse transcriptase with improved drug resistance properties . J. Med. Chem. 2004 , 47 , 5923 .
   PubMed Web of Science ®Google Scholar
• Smit , R. G. Identification and initial structure–activity relationships of a novel non-peptide quinolone GnRH receptor antagonist . Bioorg. Med. Chem. Lett. 1999 , 9 , 2615 .
   PubMed Web of Science ®Google Scholar
• Watters , W. H. ; Ramachandran , V. N. Synthesis of pyrano[3,2-c]quinolin-5-one alkaloids: Veprisine, 7-dimethylallyloxy-N-methylflindersine, and cis-3,4-dihydroxy-7-methoxy-2,2,6-trimethyl-3,4,5,6-tetrahydro-2H-pyrano[3,2-c]quinolin-5-one. J. Chem. Res., Synop. 1997, 184.
   Web of Science ®Google Scholar
• Naskar , B. ; Saha , P. ; Paira , R. ; Hazra , A. ; Paira , P. ; Mondal , S. ; Maity , A. ; Sahu , K. B. ; Banerjee , S. ; Mondal , N. B. Synthesis of polycyclic fused 2-quinolones in aqueous micellar system . Tetrahedron Lett. 2010 , 51 , 1437 .
   Web of Science ®Google Scholar
• Majumdar , K. C. ; Pal , A. K. ; Taher , A. ; Debnath , P. Highly effective regioselective method for the synthesis of substituted coumarin- and quinolone-annulated heterocycles using a palladium(0)-catalyzed reaction . Synthesis 2007 , 1707 .
   Web of Science ®Google Scholar
• Mishra , J. K. ; Samanta , K. ; Jain , M. ; Dikshit , M. ; Panda , G. Amino acid–based enantiomerically pure 3-substituted benzofused heterocycles: A new class of antithrombotic agents . Bioorg. Med. Chem. Lett. 2010 , 20 , 244 .
   PubMed Web of Science ®Google Scholar
• Seto , S. ; Tanioka , A. ; Ikeda , M. ; Izawa , S. 2-Substituted-4-aryl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,5]oxazocin-5-one as a structurally new NK1 antagonist . Bioorg. Med. Chem. Lett. 2005 , 15 , 1485 .
   PubMed Web of Science ®Google Scholar
• Xu , Y. J. ; Liu , H. ; Pan , W. ; Chen , X. ; Wong , W. C. ; Labelle , M. Improved synthesis of functionalized 5,6-dihydro-pyrimido[4,5-b][1,4]oxazepines . Tetrahedron Lett. 2005 , 46 , 7523 .
   Web of Science ®Google Scholar
• Moghaddam , F. M. ; Mirjafary , Z. ; Saeidian , H. ; Taheri , S. ; Khodabakhshi , M. R. A new and convenient approach to heterotetracyclic benzoxazocines through addition of 1,3-dicarbonyl compounds to quinolinium salts . Tetrahedron Lett. 2010 , 51 , 2704 , and references cited therein .
   Web of Science ®Google Scholar
• Kersten , L. ; Taylor , R. H. ; Felpin , F. X. Synthesis of spiro-pyridones and spiro-quinolones by sequential palladium on carbon-catalyzed allylation and ring-closing metathesis reactions . Tetrahedron Lett. 2009 , 50 , 506 .
   Web of Science ®Google Scholar
• Zhang , S. L. ; Huang , Z. S. ; Li , Y. M. ; Chan , A. S. C. ; Gu , L. Q. Synthesis of zwitterionic 4-hydroxy-2(1H)-quinolinone derivatives . Tetrahedron 2008 , 64 , 4403 .
   Web of Science ®Google Scholar
• Pirrung , M. C. ; Blume , F. Rhodium-mediated dipolar cycloaddition of diazoquinolinediones . J. Org. Chem. 1999 , 64 , 3642 .
   PubMed Web of Science ®Google Scholar
• Diaba , F. ; Houerou , C. L. ; Grignon , M. ; Gerval , P. Organosilicon entry to the regioselective cyanomethylation of quinolinium methiodides . J. Org. Chem. 2000 , 65 , 907 .
   Web of Science ®Google Scholar