Bismuth(III) Chloride–Mediated, Efficient, Solvent-Free, MWI-Enhanced Doebner Condensation for the Synthesis of (E)-Cinnamic Acids

REFERENCES

• Thoemel , F. ; Hoffmann , W. ; Degner , D. Use of etherified p-hydroxycinnamic acid esters as sunscreens . Eur. Pat. Appl. EP 44,976, February 3 , 1982 .
   Google Scholar
• Gou , D.-M. ; Liu , Y.-C. ; Chen , C.-S. A practical chemoenzymic synthesis of the taxol C-13 side chain N-benzoyl-(2R,3S)-3-phenylisoserine . J. Org. Chem. 1993 , 58 , 1287 .
   Web of Science ®Google Scholar
• Koo , J. ; Fish , M. S. ; Walker , G. N. ; Blake , 2,3-Dimethoxycinnamic acid . J. Org. Synth. Coll. 1963 , 4 , 327 .
   Google Scholar
• (a) Jackson , J. G. ; Kenner , J. The reactivity of the double bond in coumarins and related α β-unsaturated carbonyl compounds, part I: Addition of cyanoacetamide to coumarins . J. Chem. Soc. 1928 , 166 ; (b) Walling , C. ; Walfstirm , K. Derivatives of piperazine, XXI: Synthesis of piperazine and C-substituted piperazines . J. Am. Chem. Soc. 1947 , 69 , 854 .
   Google Scholar
• Claisen , L. Zur Darstellung der zimmtsäure und ihrer homologen . Chem. Ber. 1890 , 23 , 976 ; (b) Marvel , C. S. ; King , W. O. Ethyl cinnamate . Org. Synth. Coll. 1941 , 1 , 252 .
   Google Scholar
• Johnson , A. L. Synthesis of the three isomeric ortho-substituted phenylthienyl benzoic acids . J. Org. Chem. 1976 , 41 , 1320 .
   Web of Science ®Google Scholar
• Patil , V. J. ; Mavers , U. Wittig reactions in the presence of silica gel . Tetrahedron Lett. 1996 , 37 , 1281 ; (b) Schiemenz , G. P. ; Thobe , J. Aromatische phosphine mit substituenten zweiter ordnung, III: Eine neue variante der Wittig-Reaktion . Chem. Ber. 1966 , 99 , 2663 .
   Web of Science ®Google Scholar
• Gruber , A. S. ; Pozebon , D. ; Monteiro , A. L. ; Dupont , J. On the use of phosphine-free PdCl2(SEt2)2 complex as catalyst precursor for the Heck reaction . Tetrahedron Lett. 2001 , 42 , 7345 .
   Web of Science ®Google Scholar
• (a) Baruah , B. ; Prajapati , D. ; Baruah , A. ; Sandhu , J. S. BiCl3/CdCl3-catalysed Michael addition of 1,3-dicarbonyl compounds under microwave irradiations. Tetrahedron Lett. 1997, 38, 1449; (b) Borah , H. N. ; Prajapati , D. ; Sandhu , J. S. ; Ghosh , A. C. Bismuth(III)chloride–zinc–promoted selective reduction of aromatic nitro compounds to azoxy compounds. Tetrahedron Lett. 1994, 35, 3167; (c) Boruah , A. ; Baruah , B. ; Prajapati , D. ; Sandhu , J. S. Bi+3-catalysed regeneration of carbonyl compounds from hydrazones under microwave irradiations. Synlett 1997, 1251; (d) Thakur , A. J. ; Boruah , A. ; Prajapati , D. ; Sandhu , J. S. Microwave-induced bismuth trichloride–catalysed Beckmann rearrangement of oximes. Synth. Commun. 2000, 30, 2105; (e) Wada , M. ; Ohki , H. ; Akiba , K. Y. A Grignard-type addition of allyl unit to aldehydes by using bismuth and bismuth salt. Bull. Chem. Soc. Jpn. 1990, 63, 1738; (f) Suzuki , H. ; Ikegami , T. ; Matano , Y. Bismuth in organic transformations. Synthesis 1997, 249; (g) Vidal , S. Bismuth(III) derivatives: New catalysts. Synlett 2001, 1194; (h) De , S. K. ; Gibbs , R. A. An efficient and practical procedure for the synthesis of 4-substituted coumarins. Synthesis 2005, 1231–1233; (i) Ramalinga , K. ; Vijayalakshmi , P. ; Kaimal , T. N. B. Bismuth(III)-catalyzed synthesis of dihydropyrimidinones: Improved protocol conditions for the Biginelli reaction. Synlett 2001, 863.
   Web of Science ®Google Scholar
• Bhuyan , P. J. ; Boruah , R. C. ; Sandhu , J. S. Studies on uracil, a facile one-pot synthesis of pyrido (2,3-d) and pyrazolo (3,4-d) pyrimidines . J. Org. Chem. 1990 , 55 , 568 .
   Web of Science ®Google Scholar
• (a) Vogel , A. I. A Textbook of Practical Organic Chemistry, , 5th ed. ; Addison Wesley Longman : London , 1998 , p. 1041 ; (b) Aldrich Catalog Handbook of Fine Chemicals ; Aldrich : Delhi , India , 2007–2008 .
   Google Scholar