Tungstophosphoric Acid–Catalyzed Imino-Diels–Alder Reaction: An Efficient One-Pot Synthesis of Pyrano- and Furanoquinoline Derivatives

REFERENCES

• Johnson , J. V. ; Rauckman , B. S. ; Beccanari , P. D. ; Roth , B. 2,4-Diamino-5-benzylpyrimidines and analogs as antibacterial agents, 12: 1,2-Dihydroquinolylmethyl analogs with high activity and specificity for bacterial dihydrofolate reductase . J. Med. Chem. 1989 , 32 , 1942 .
   PubMed Web of Science ®Google Scholar
• Yamada , N. ; Kadowaki , S. ; Takahashi , K. ; Umeza , K. MY-1250, a major metabolite of the anti-allergic drug repirinast, induces phosphorylation of a 78-kD a protein in rat mast cells . Biochem. Pharmacol. 1992 , 44 , 1211 .
   PubMed Web of Science ®Google Scholar
• Wood , E. ; Crosby , R. M. ; Dickerson , S. ; Frye , S. V. ; Griffin , R. ; Hunter , R. ; Jung , D. K. ; McDonald , O. B. ; McNutt , R. ; Mahony , W. B. ; Peel , M. R. ; Ray , J. A prodrug approach to the design of cRaf1 kinase anhibitors with improved cellular activity. Anti-Cancer Drug Des. 2001, 16, 1.
   PubMedGoogle Scholar
• Ramesh , M. ; Mohan , P. S. ; Shanmugam , P. A convenient synthesis of flindersine, atanine, and their analogues . Tetrahedron 1984 , 40 , 4041 .
   Web of Science ®Google Scholar
• Quraishi , M. A. ; Thakur , V. R. ; Dhawan , S. N. Synthesis of 6-(4-chlor phenyl)-7H-indeno[2,1-C] quinolines and their biological activity . Indian J. Chem. 1989 , 28B , 891 .
   Google Scholar
• Boger , D. L. ; Weinreb , S. M. Hetero-Diels–Alder Methodology in Organic Synthesis ; Academic Press: San Diego, 1987; Chaps. 2 and 9 .
   Google Scholar
• Weinreb , S. M . In Comprehensive Organic Synthesis ; B. M. Trost , and I. Fleming (Eds.); Pergamon, Oxford, 1991; vol. 5, p. 401 .
   Google Scholar
• Babu , G. ; Perumal , P. T. Convenient synthesis of pyrano[3,2-c] quinolines and indeno[2,1-c] quinolines by imino Diels–Alder reaction . Tetrahedron Lett. 1998 , 39 , 3225 .
   Web of Science ®Google Scholar
• Ma , Y. ; Qian , C. ; Xie , M. ; Sun , J. Lanthanide chloride–catalyzed imino Diels–Alder reaction one-pot synthesis of pyrano[3,2-c]-and furo[3,2-c] quinolines . J. Org. Chem. 1999 , 64 , 6462 .
   Web of Science ®Google Scholar
• Yadav , J. S. ; Reddy , B. V. S. ; Srinivas , R. ; Madhuri , C. ; Ramalingam , T. Lithium perchlorate/diethylether–catalyzed aza-Diels–Alder reaction: An expeditious synthesis of pyrano, indeno quinolines and phenanthridines . Synlett 2001 , 240 .
   Google Scholar
• Yadav , J. S. ; Reddy , B. V. S. ; Sunitha , V. ; Reddy , K. S. Novel use of Selectfluor for the synthesis of cis-fused pyrano- and furanotetrahydroquinolines . Adv. Synth. Catal. 2003 , 345 , 1203 .
   Google Scholar
• Zhou , Z. ; Xu , F. ; Han , X. ; Zhou , J. ; Shen , Q. Stereoselective synthesis of pyrano[3,2-c]- and furano[3,2-c]quinolines: Samarium diiodide–catalyzed one-pot aza-Diels–Alder reactions . Eur. J. Org. Chem. 2007 , 5265 .
   Google Scholar
• Das , B. ; Reddy , K. R. ; Ramu , R. ; Thirupathi , P. ; Ravikanth , B. Iodine as an efficient catalyst for one-pot multicomponent synthesis of β-acetamido ketones . Synlett 2006 , 1756 .
   Web of Science ®Google Scholar
• Das , B. ; Reddy , V. S. ; Tehseen , F. ; Krishnaiah , M. Catalyst-free highly regio- and stereo-selective ring opening of epoxides and aziridines with sodium azide using poly(ethylene glycol) as an efficient reaction medium . Synthesis 2007 , 666 .
   Google Scholar
• Das , B. ; Krishnaiah , M. ; Balasubramanyam , P. ; Veeranjaneyulu , B. ; Kumar , D. N. A remarkably simple N-formylation of anilines using polyethylene glycol . Tetrahedron Lett. 2008 , 49 , 2225 .
   Web of Science ®Google Scholar
• Pizzio , L. R. ; Cáceres , C. V. ; Blanco , M. N. Acid catalysts prepared by impregnation of tungstophospohoric acid solutions on different supports . Appl. Catal. A. 1998 , 167 , 283 .
   Web of Science ®Google Scholar
• Soeda , H. ; Okuhara , T. ; Misono , M. Selective alkylation of p-xylene with 2-methylpropene by 12-tungstophosphoric acid . Chem. Lett. 1994 , 909 .
   Google Scholar
• Kozhevnikov , I. V. Heteropoly acids and related compounds as catalysts for fine chemical synthesis. Catal. Rev. Sci. Eng. 1995 , 37 , 311 .
   Web of Science ®Google Scholar
• Part 176 in the series “Studies on novel synthetic methodologies.”
   Google Scholar