Synthesis of Biscoumarins from 4-Hydroxycoumarin and Aromatic Aldehydes—A Comparative Assessment of Percentage Yield Under Thermal and Microwave-Assisted Conditions

REFERENCES

• Overmann , R. S. ; Stahmann , M. A. ; Heubner , C. F. ; Sullivan , W. R. ; Spero , L. ; Doherty , D. G. ; Ikawa , M. ; Graf , L. ; Roseman , S. ; Link , K. P. Studies on the hemorrhagic sweet clover disease, 13: Anticoagulant activity and structure in the 4-hydroxycoumarin group . J. Biol. Chem. 1944 , 153 , 5 – 24 .
   Google Scholar
• Kostava , I. ; Manolov , I. ; Nicolova , I. ; Konstantonov , S. ; Karaivanova , M. New lanthanide complexes of 4-methyl-7-hydroxycoumarin and their pharmacological activity . Eur. J. Med. Chem. 2001 , 36 ( 4 ), 339 – 347 .
   PubMed Web of Science ®Google Scholar
• Chohan , Z. H. ; Shaikh , A. U. ; Rauf , A. ; Supuran , C. T. Antibacterial, antifungal and cytotoxic properties of novel N-substituted sulfonamides from 4-hydroxycoumarin . J. Enzym. Inhib. Med. Chem. 2006 , 21 ( 6 ), 741 – 748 .
   PubMed Web of Science ®Google Scholar
• Jung , J. C. ; Lee , J. H. ; Oh , S. ; Lee J. G. : Park , O. S. Synthesis and antitumor activity of 4-hydroxycoumarin derivatives . Bioorg. Med. Chem. Lett. 2004 , 14 ( 22 ), 5527 – 5531 .
   PubMed Web of Science ®Google Scholar
• Zhao , H. ; Neamati , N. ; Hong , H. ; Mazumder , A. ; Wang , S. ; Sunder , S. ; Milne , G. W. A. ; Pommier , Y. ; Burke , T. R. Coumarin-based inhibitors of HIV integrase . J. Med. Chem. 1997 , 40 ( 2 ), 242 – 249 .
   PubMed Web of Science ®Google Scholar
• Singer , L. A. ; Kong , N. P. Vinyl radicals: Stereoselectivity in hydrogen atom transfer to equilibrated isomeric vinyl radicals . J. Am. Chem. Soc. 1966 , 88 ( 22 ), 5213 .
   Web of Science ®Google Scholar
• Bhat , A. N. ; Jain , B. D. Analytical applications of 3-acetyl-4-hydroxycoumarin—II: Spectrophotometric determination of iron . Talanta 1960 , 5 ( 3–4 ), 271 – 275 .
   Google Scholar
• Appendino , G. ; Cravotto , G. ; Tagliapietra , S. ; Ferraro , S. ; Nano , G. M. ; Palmisano , G. The chemistry of coumarin derivatives, part 3: Synthesis of 3-alkyl-4- hydroxycoumarins by reductive fragmentation of 3,3-dihydroxybis[coumarins] . Helv. Chim. Acta 1991 , 74 ( 7 ), 1451 – 1458 .
   Google Scholar
• Manolov , I. ; Moessmer , C. M. ; Danchev , N. D. Synthesis, structure, toxicological and pharmacological investigations of 4-hydroxycoumarin derivatives. Eur. J. Med. Chem. 2006, 41(7), 882–890.
   PubMed Web of Science ®Google Scholar
• Murray , R. D. H. ; Mendez , J. ; Brown , S. A. The Natural Coumarins: Occurrence, Chemistry and Biochemistry ; Wiley & Sons : Chichester , 1982 .
   Google Scholar
• Lehmann , J. Thrombosis treatment and prevention with methylene-bis-(hydroxycoumarin) . The Lancet 1943 , 241 ( 6246 ), 611 – 613 .
   Google Scholar
• Heubner , C. F. ; Sullivan , W. R. ; Stahmann , M. A. ; Link , K. P. Studies on 4-hydroxycoumarin, III: Dehydration of the aldehyde condensation products . J. Am. Chem. Soc. 1943 , 65 ( 12 ), 2292 – 2296 .
   Google Scholar
• Khan , K. M. ; Iqbal , S. ; Lodhi , M. A. ; Maharvi , G. M. ; Zia-u-Allah ; Choudhary , M. I. ; Rahman , A. U. ; Perveen , S. Biscoumarin: New class of urease inhibitors: Economical synthesis and activity . Bioorg. Med. Chem. 2004 , 12 ( 8 ), 1963 – 1968 .
   PubMed Web of Science ®Google Scholar
• Kidwai , M. ; Bansal , V. ; Mothsra , P. ; Saxena , S. ; Somvanshi , R. K. ; Dey , S. ; Singh , T. P. Molecular iodine: A versatile catalyst for the synthesis of bis(4-hydroxycoumarin) methanes in water . J. Mol. Catalys A: Chem. 2007 , 268 ( 1–2 ), 76 – 81 .
   Google Scholar
• Lidstrom , P. ; Tierney , J. ; Wathey , B. ; Westman , J. Microwave assisted organic synthesis—a review . Tetrahedron 2001 , 57 ( 45 ), 9225 – 9283 .
   Web of Science ®Google Scholar
• (a) Perreux , L. ; Loupy , A. A tentative rationalization of microwave effects in organic synthesis according to the reaction medium and mechanistic considerations . Tetrahedron 2001 , 57 , 9199 – 9223 ; (b) Gabriel , C. ; Gabriel , S. ; Grant , E. H. ; Halstead , B. S. J. ; Mingos , D. M. P. Dielectric parameters relevant to microwave dielectric heating . Chem. Soc. Rev. 1998 , 27 , 213 – 223 .
   Web of Science ®Google Scholar
• Baghurst , D. R. ; Mingos , D. M. P. Superheating effects associated with microwave dielectric heating . J. Chem. Soc., Chem. Commun. 1992 , 674 – 677 .
   Google Scholar