Novel Synthesis of Bis-Iminocoumarins

REFERENCES

• Ukhov , S. V. ; Kon'shin , M. E. ; Novikova , V. V. ; Odegova , T. F. Synthesis and antimicrobial activity of silver salts of substituted 2-iminocoumarin-3-carboxylic acid amides . Pharm. Chem. J. 2004 , 38 , 186 – 187 .
   Google Scholar
• Burke , B. L. ; Marquez , V. E. ; Li , Z.-H. ; Bolen , J. B. ; Stefanova , I. ; Horak , I. D. Bicyclic compounds as ring-constrained inhibitors of protein-tyrosine kinase p56lck . J. Med. Chem. 1993 , 36 ( 4 ), 425 – 432 .
   PubMed Web of Science ®Google Scholar
• Srivastava , S. K. ; Tripathi , R. P. ; Ramachandran , R. NAD+-dependent DNA ligase (Rv3014c) from mycobacterium tuberculosis crystal structure of the adenylation domain and identification of novel inhibitors. J. Biol. Chem. 2005, 280, 30273–30281.
   PubMed Web of Science ®Google Scholar
• Karasev , A. A. ; Lukatskaya , L. L. ; Rubtsov , M. I. ; Zhikol , E. K. ; Yarmolenko , S. N. ; Ponomarev , O. A. Synthesis, protolytic equilibria, and stability of 2-amino-3-(2-benzimidazolyl)-1-benzopyrylium salts in water–alcohol medium . Russ. J. Gen. Chem. 1995 , 65 ( 2 ), 1416 – 1425 .
   Google Scholar
• Huang , S.-T. ; Jian , J.-L. ; Peng , H.-Z. ; Wang , K.-L. ; Lin , C.-M. ; Huang , C.-H. ; Yang , T. C.-K. The synthesis and optical characterization of novel iminocoumarin derivatives . Dyes Pigm. 2010 , 86 , 6 – 14 .
   Web of Science ®Google Scholar
• Syzova , Z. A. ; Doroshenko , A. O. ; Lukatskaya , L. L. ; Rubtsov , M. I. ; Karasyov , A. A. Bichromophoric fluorescent dyes with rigid molecular structure: Fluorescence ability regulation by the photoinduced intramolecular electron transfer . J. Photochem. Photobiol. A 2004 , 165 , 59 – 68 .
   Web of Science ®Google Scholar
• Borisov , A. V. ; Gorobets , N. Y. ; Yermolayev , S. A. ; Zhuravel' , I. O. ; Kovalenko , S. M. ; Desenko , S. M. One-pot microwave-assisted synthesis of a benzopyrano[2,3-c]pyrazol-3(2H)-one library . J. Comb. Chem. 2007 , 9 , 909 – 911 .
   PubMed Web of Science ®Google Scholar
• O'Callaghan , C. N. ; McMurry , T. B. H. ; O'Brien , J. E. ; Draper , S. M. ; Wilcock , D. J. Formation of polyheterocyclic systems by reaction of 2-imino-4-methyl-2H-1-benzopyran-3-carbonitrile with active methylene compounds . J. Chem. Soc., Perkin Trans. 1 1996 , 1067 – 1071 .
   Google Scholar
• Bilokin , Y. V. ; Kovalenko , S. N. ; Bylov , I. E. ; Chernykh , V. P. Rearrangements of 2-imino-2H-1-benzopyran-3-carboxamides under action of anthranilic acid as N-nucleophile . Heterocycl. Commun. 1998 , 4 , 257 – 260 .
   Web of Science ®Google Scholar
• Borisov , A. V. ; Dzhavakhishvili , S. G. ; Zhuravel , I. O. , Kovalenko , S. M. ; Nikitchenko , V. M. Parallel liquid-phase synthesis of benzopyrano[2,3-d]pyrimidine libraries . J. Comb. Chem. 2007 , 9 , 5 – 8 .
   PubMed Web of Science ®Google Scholar
• Turki , H. ; Abid , S. ; Le Bigot , Y. ; Fery-Forgues , S. ; El Gharbi , R. Novel synthesis of 2-oxo-2H-benzopyrano[2,3-d]pyrimidines . Synth. Commun. 2004 , 34 , 3553 – 3563 .
   Web of Science ®Google Scholar
• Turki , H. ; Genestie , B. ; El Gharbi , R. ; El Boussiry , S. ; Banoub , J. Gas-phase fragmentation study of a novel series of synthetic 2-oxo-2H-benzopyrano[2,3-d]pyrimidine derivatives using electrospray ionization tandem mass spectroscopy measured with a quadrupole orthogonal time-of-flight hybrid instrument . Rapid Commun. Mass Spectrom. 2008 , 23 ( 2 ), 267 – 281 .
   Web of Science ®Google Scholar
• Kammoun , M. ; Turki , H. ; El Gharbi , R. ; Fery-Forgues , S. Reactivity of 3-cyano-N-ethoxycarbonyl-iminocoumarin with hydrazides as N-nucleophiles . J. Heterocycl. Chem. 2009 , 46 ( 1 ), 28 – 32 .
   Web of Science ®Google Scholar
• Kammoun , M. ; Turki , H. ; Fery-Forgues , S. ; El Gharbi , R. Convenient synthesis of a new series of 3-triazolonyl iminocoumarins . Synth. Commun. 2010 , 40 ( 6 ), 888 – 900 .
   Web of Science ®Google Scholar
• Volmajer , J. ; Toplak , R. ; Lebanb , I. ; Le Marechala , A. M. Synthesis of new iminocoumarins and their transformations into N-chloro and hydrazono compounds . Tetrahedron 2005 , 61 , 7012 – 7021 .
   Web of Science ®Google Scholar
• Gorobets , N. Yu. ; Abakumov , V. V. ; Borisov , A. V. ; Nikitchenko , V. M. Novel aspects of the reaction of 3-(benzimidazol-2-yl)-2-iminocoumarins with aromatic aldehydes . Chem. Heterocycl. Comp. 2004 , 40 ( 3 ), 334 – 342 .
   Google Scholar
• Fadda , A. A. ; Zeimaty , M. T. ; Gerges , M. M. ; Refat , H. M. ; Biehl , E. R. Base-catalyzed condensation of malononitrile and 2-hydroxy-1-naphtaldehyde with diffrent ketones . Heterocycles 1996 , 43 , 23 .
   Web of Science ®Google Scholar
• Turki , H. ; Abid , S. ; Fery-Forgues , S. ; El Gharbi , R. Optical properties of new fluorescent iminocoumarins: Part 1 . Dyes Pigm. 2007 , 73 , 311 – 316 .
   Web of Science ®Google Scholar
• Turki , H. ; Abid , S. ; Gharbi , R. ; Fery-Forgues , S. Optical properties of new fluorescent iminocoumarins, part 2: Solvatochromic study and comparison with the corresponding coumarin. C. R. Chimie 2006, 9, 1252–1259.
   Web of Science ®Google Scholar
• Fakhfakh , M. ; Turki , H. ; Abid , S. ; El Gharbi , R. ; Fery-Forgues , S. Preparation and optical properties of new fluorescent iminocoumarins: Study of N-acyl-derivatives . J. Photochem. Photobiol. A 2007 , 185 , 13 – 18 .
   Web of Science ®Google Scholar
• Fakhfakh , M. ; Turki , H. ; Fery-Forgues , S. ; El Gharbi , R. The synthesis and optical properties of novel fluorescent iminocoumarins and bis-iminocoumarins: Investigations in the series of urea derivatives . Dyes Pigm. 2010 , 84 , 108 – 113 .
   Web of Science ®Google Scholar
• Benmaktouf , L. ; Ammar , H. ; Le Bigot , Y. ; Abid , S. Synthesis of new iminocoumarins bearing parabanic moieties . Synth. Commun. 2011 , 41 , 1017 – 1026 .
   Web of Science ®Google Scholar
• Khan , K. M. ; Iqbal , S. ; Lodhi , M. A. ; Maharvi , G. M. ; Ullah , Z. ; Choudhary , M. I. ; Atta-ur-R ; Perveen , S. Biscoumarin: New class of urease inhibitors: Economical synthesis and activity . Bioorgan. Med. Chem. 2004 , 12 , 1963 – 1968 .
   PubMed Web of Science ®Google Scholar
• Nagashima , R. ; Levy , G. ; Sarcione , E. J. Comparative pharmacokinetics of coumarin anticoagulants III: Factors affecting the distribution and elimination of bishydroxycoumarin (BHC) in isolated liver perfusion studies . J. Pharmaceut. Sci. 1968 , 57 , 1881 – 1888 .
   PubMed Web of Science ®Google Scholar
• Mercep , M. ; Malvar , I. ; Hrvacic , B. ; Markovic , S. ; Filipovic-Sucic , A. ; Bosnjak , B. ; Cempuh-Klonkay , A. ; Rupcic , R. ; Hutinec , A. ; Elenkov , I. J. ; Mesic , M. Bis-(coumarin) componds with anti-inflammatory activity . WO patent 2006111858 , 2006 .
   Google Scholar
• Romeo , A. ; Prosdocimi , M. New coumarin derivatives . WO patent 9222545 , 1992 .
   Google Scholar
• Kostova , I. ; Momekov , G. New zirconium(IV) complexes of coumarins with cytotoxic activity . Eur. J. Med. Chem. 2006 , 41 , 717 – 726 .
   PubMed Web of Science ®Google Scholar
• Ammar , H. ; Fery-Forgues , S. ; El Gharbi , R. UV/vis absorption and fluorescence spectroscopic study of novel symmetrical biscoumarin dyes . Dyes Pigm. 2003 , 57 , 259 – 265 .
   Web of Science ®Google Scholar
• Ammar , H. ; Abid , S. ; Fery-Forgues , S. Synthesis and spectroscopic study of new biscoumarin dyes based on 7-(4-methylcoumarinyl) diesters . Dyes Pigm. 2008 , 78 , 1 – 7 .
   Web of Science ®Google Scholar
• Asimov , M. M. ; Nikitchenko , V. M. ; Novikov , A. I. ; Rubinov , A. N. ; Bor , Z. ; Gati , L. New high-efficiency biscoumarin laser dyes . Chem. Physics Lett. 1988 , 149 ( 2 ), 140 – 144 .
   Web of Science ®Google Scholar
• Ammar , H.; Le Bigot Y.; El Gharbi R. Synthèse des biscoumarines en milieu biphasique solide/liquide 1: Condensation de l'aldéhyde salicilique avec le m-phénylène diacétonitrile . J. Soc. Chim. Tunisie 2001 , 4 ( 9 ), 915 – 923 .
   Google Scholar
• Ammar , H. ; Le Bigot , Y. ; El Gharbi , R. Synthèse des biscoumarines en milieu biphasique solide/liquide 2: Application de la réaction de Knoevenagel à l'obtention de 3,3′-phénylènebiscoumarines . J. Soc. Chim. Tunisie 2001 , 4 ( 10 ), 1239 – 1244 .
   Google Scholar
• Ammar , H. ; Fakhfakh , M. ; Le Bigot , Y. ; El Gharbi , R. Synthesis of new bis-iminocoumarins by Schmidt reaction catalyzed by ion-exchange resins . Synth. Commun. 2003 , 33 ( 11 ), 1821 – 1828 .
   Web of Science ®Google Scholar