Boric Acid–Catalyzed One-Pot Access to 7-Aryl-benzopyrano[4,3-b] benzopyran-6,8-diones Under Aqueous Micellar Conditions

REFERENCES

• Ganem , B. Strategies for innovation in multicomponent reaction design . Acc. Chem. Res. 2009 , 42 , 463 – 472 .
   PubMed Web of Science ®Google Scholar
• Breinbauer , R. ; Vetter , I. R. ; Waldmann , H. From protein domains to drug candidates—natural products as guiding principles in the design and synthesis of compound libraries . Angew. Chem., Int. Ed. 2002 , 41 , 2878 – 2890 .
   Web of Science ®Google Scholar
• Liao , Y. ; Hu , Y. ; Wu , J. ; Zhu , Q. ; Donovan , M. ; Fathi , R. ; Yang , Z. Diversity-oriented synthesis and branching reaction pathway to generate natural product-like compounds . Curr. Med. Chem. 2003 , 10 , 2285 – 2316 .
   PubMed Web of Science ®Google Scholar
• Pirrung , M. C. ; Das Sharma , K. Aqueous medium effects on multi-component reactions . Tetrahedron 2005 , 61 , 11456 – 11472 .
   Web of Science ®Google Scholar
• Tang , Y. ; Oppenheimer , J. ; Song , Z. ; You , L. ; Zhang , X. ; Hsung , R. P. Strategies and approaches for constructing 1-oxadecalins . Tetrahedron 2006 , 62 , 10785 – 10813 , and references cited therein .
   Web of Science ®Google Scholar
• Kumar , S. ; Hernandez , D. ; Hoa , B. ; Lee , Y. ; Yang , J. S. ; McCurdy , A. Synthesis, photochromic properties, and light-controlled metal complexation of a naphthopyran derivative. Org. Lett. 2008, 10, 3761–3764.
   PubMed Web of Science ®Google Scholar
• Hamdi , N. ; Puerta , M. C. ; Valerga , P. Synthesis, structure, antimicrobial, and antioxidant investigations of dicoumarol and related compounds . Eur. J. Med. Chem. 2008 , 43 , 2541 – 2548 .
   PubMed Web of Science ®Google Scholar
• Stanchev , S. ; Momekov , G. ; Jensen , F. ; Manolov , I. Synthesis, computational study, and cytotoxic activity of new 4-hydroxycoumarin derivatives . Eur. J. Med. Chem. 2008 , 43 , 694 – 706 .
   PubMed Web of Science ®Google Scholar
• Khurana , J. M. ; Nand , B. ; Saluja , P. DBU: A highly efficient catalyst for one-pot synthesis of substituted 3,4-dihydropyrano[3,2-c]chromenes, dihydropyrano[4,3-b]pyranes, 2-amino-4H-benzo[h]chromenes, and 2-amino-4H benzo[g]chromenes in aqueous medium . Tetrahedron 2010 , 66 , 5637 – 5641 .
   Web of Science ®Google Scholar
• Heravi , M. M. ; Sadjadi , S. ; Haj , N. M. ; Oskooie , H. A. ; Bamoharram , F. F. Role of various heteropolyacids in the reaction of 4-hydroxycoumarin, aldehydes, and ethylcyanoacetate . Catal. Commun. 2009 , 10 , 1643 – 1646 .
   Web of Science ®Google Scholar
• Gong , K. ; Wang , H. ; Luo , J. ; Liu , Z.-L. One-pot synthesis of polyfunctionalized pyrans catalyzed by basic ionic liquid in aqueous media . J. Heterocycl. Chem. 2009 , 46 , 1145 – 1150 .
   Web of Science ®Google Scholar
• Khurana , J. M. ; Kumar , S. Tetrabutylammonium bromide (TBAB): A neutral and efficient catalyst for the synthesis of biscoumarin and 3,4-dihydropyrano[c]chromene derivatives in water and solvent-free conditions . Tetrahedron Lett. 2009 , 50 , 4125 – 4127 .
   Web of Science ®Google Scholar
• Chen , Z. ; Zhu , Q. ; Su , W. A novel sulfonic acid–functionalized ionic liquid–catalyzed multicomponent synthesis of 10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-dione derivatives in water . Tetrahedron Lett. 2011 , 52 , 2601 – 2604 .
   Web of Science ®Google Scholar
• Liang , B. ; Kalidindi , S. ; Proco , J. A. ; Stephenson , C. R. Multicomponent reaction discovery: Three-component synthesis of spirooxindoles . Org. Lett. 2010 , 12 , 572 – 575 .
   PubMed Web of Science ®Google Scholar
• Ganguly , N. C. ; Barik , S. K. A facile efficient mild deprotection protocol of 1,3-dithianes and 1,3-dithiolanes with 30% hydrogen peroxide and iodine catalyst in aqueous micellar system . Synthesis 2009 , 1393 – 1399 .
   Web of Science ®Google Scholar
• Ganguly , N. C. ; Roy , S. ; Mondal , P. ; Saha , R. An efficient one-pot organocatalytic synthesis of 9-(1H-indol-3-yl)-xanthen-4-(9H)-ones under mild aqueous micellar conditions . Tetrahedron Lett. 2012 , 53 , 7067 – 7071 .
   Web of Science ®Google Scholar
• Cotton , F. A. ; Wilkinson , G. ; Murillo , C. A. ; Bochmann , M. Advanced Inorganic Chemistry, , 6th ed. ; Wiley-Interscience : New York , 1999 .
   Google Scholar
• Tu , S. ; Fang , F. ; Miao , C. ; Jiang , H. ; Feng , Y. ; Shi , D. ; Wang , X. One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using boric acid as catalyst . Tetrahedron Lett. 2003 , 44 , 6153 – 6155 .
   Web of Science ®Google Scholar
• Mukhopadhyay , C. ; Datta , A. ; Butcher , R. J. Highly efficient one-pot, three-component Mannich reaction catalysed by boric acid and glycerol in water with major syn diastereoselectivity . Tetrahedron Lett. 2009 , 50 , 4246 – 4250 .
   Web of Science ®Google Scholar
• Manabe , K. ; Mori , Y. ; Wakabayashi , T. ; Nagayama , S. ; Kobayashi , S. Organic synthesis inside particles in water: Lewis acid-surfactant-combined catalysts for organic reactions in water using colloidal dispersions as reaction media . J. Am. Chem. Soc. 2000 , 122 , 7202 – 7207 .
   Web of Science ®Google Scholar