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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 19
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Original Articles

Synthesis of 2-Amino-4-(2-hydroxynaphthyl)-4H-chromene-3-carbonitriles by Michael Addition and Their Transformation into New Pentacyclic Compounds

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Pages 2870-2878 | Received 16 Apr 2014, Published online: 06 Aug 2014

REFERENCES

  • Polshettiwar , V. ; Varma , R. S. Greener and sustainable approaches to the synthesis of pharmaceutically active heterocycles . Curr. Opin. Drug Discov. Devel. 2007 , 10 , 723 – 737 .
  • Padwa , A. ; Bur , S. K. The domino way to heterocycles . Tetrahedron 2007 , 63 , 5341 – 5378 .
  • D'Souza , D. M. ; Muller , T. J. Multi-component syntheses of heterocycles by transition-metal catalysis . Chem. Soc. Rev. 2007 , 36 , 1095 – 1108 .
  • Dadiboyena , S. Cycloadditions and condensations as essential tools in spiropyrazoline synthesis . Eur. J. Med. Chem. 2013 , 63 , 347 – 377 .
  • DeSimone , R. W. ; Currie , K. S. ; Mitchell , S. A. ; Darrow , J. W. ; Pippin , D. A. Privileged structures: Applications in drug discovery . Comb. Chem. High Throughput Screen. 2004 , 7 , 473 – 494 .
  • Khan , I. ; Ibrar , A. ; Abbas , N. ; Saeed , A. Recent advances in the structural library of functionalized quinazoline and quinazolinone scaffolds: Synthetic approaches and multifarious applications . Eur. J. Med. Chem. 2014 , 76 ( 9 ), 193 – 244 .
  • Shaabani , A. ; Rezayan , A. H. ; Sarvary , A. ; Rahmati , A. ; Khavasi , H. R. Pyridine-catalyzed reaction of tetracyanoethylene and activated 1,3-dicarbonyl CH-acid compounds: A rapid and efficient synthesis of pyran annulated heterocyclic systems . Catal. Commun. 2008 , 9 ( 6 ), 1082 – 1086 .
  • Khan , A. T. ; Lal , M. ; Ali , S. ; Khan , Md. M. One-pot three-component reaction for the synthesis of pyran annulated heterocyclic compounds using DMAP as a catalyst. Tetrahedron Lett. 2011, 52(41), 5327–5332.
  • Sandeep , K. ; Ramendra , P. ; Abhinav , K. ; Brijesh , K. ; Vishnu , K. T. ; Vishnu , J. R. Synthesis of dibenzo[d,f]diazepinones and alkenylindolinones through ring transformation of 2H-pyran-2-one-3-carbonitriles by indolin-2-ones . Tetrahedron 2013 , 69 ( 24 ), 4857 – 4865 .
  • Yongjun , L. ; Ying , L. ; Dongju , Z. ; Haiquan , H. ; Chengbu , L. Theoretical investigation on second-order nonlinear optical properties of (dicyanomethylene)-pyran derivatives . J. Mol. Struct. 2011 , 570 ( 1 ), 43 – 51 .
  • Sayaree , D. ; Dipak , K. R. ; Somnath , S. R. ; Swapnadip , R. ; Sudin , B. ; Subhash , C. B. Effect of solvent environment on the photophysics of a newly synthesized bioactive 7-oxy(5-selenocyanato-pentyl)-2H-1-benzopyran-2-one . J. Luminesc. 2012 , 132 ( 4 ), 957 – 964 .
  • Majumdar , K. C. ; Ghosh , S. K. Studies of bioactive heterocycles: Facile thio-Claisen rearrangement of propargylthio[1]benzopyran-2-ones . Tetrahedron Lett. 2002 , 43 ( 11 ), 2115 – 2117 .
  • Hasan , S. M. ; Alam , M. M. ; Husain , A. ; Khanna , S. ; Akhtar , M. ; Zaman , M. S. Synthesis of 6-aminomethyl derivatives of benzopyran-4-one with dual biological properties: Anti-inflammatory, analgesic, and antimicrobial . Eur. J. Med. Chem. 2009 , 44 ( 12 ), 4896 – 4903 .
  • Fernandes , M. J. G. ; Sameiro , M. ; Gonçalves , T. ; Costa , S. P. G. Neurotransmitter amino acid—oxobenzo[f]benzopyran conjugates: Synthesis and photorelease studies . Tetrahedron 2008 , 64 ( 49 ), 11175 – 11179 .
  • Calderone , V. ; Testai , L. ; Martelli , A. ; Rapposelli , S. ; Digiacomo , M. ; Balsamo , A. ; Breschi , M. C. Anti-ischemic properties of a new spiro-cyclic benzopyran activator of the cardiac mito-KATP channel . Biochem. Pharmacol. 2010 , 79 ( 1 ), 39 – 47 .
  • Rapposelli , S. ; Breschi , M. C. ; Calderone , V. ; Digiacomo , M. ; Martelli , A. ; Testai , L. ; Vanni , M. ; Balsamo , A. Synthesis and biological evaluation of 5-membered spiro heterocycle-benzopyran derivatives against myocardial ischemia . Eur. J. Med. Chem. 2011 , 46 ( 3 ), 966 – 973 .
  • Iizuka , K. ; Morita , N. ; Murakami , T. ; Kawaguchi , H. Nipradilol inhibits atmospheric pressure-induced cell proliferation in human aortic smooth muscle cells . Pharmacol. Res. 2004 , 49 ( 3 ), 217 – 225 .
  • Hong , L. ; Xi , J. ; Zhang , Y. ; Tian , W. ; Xu , J. ; Cui , X. ; Xu , Z. Atrial natriuretic peptide prevents the mitochondrial permeability transition pore opening by inactivating glycogen synthase kinase 3β via PKG and PI3K in cardiac H9c2 cells . Eur. J. Pharmacol. 2012 , 695 ( 1 ), 13 – 19 .
  • Elomri , A. ; Mitaku , S. ; Michel , S. ; Skaltsounis , A.-L. ; Tillequin , F. ; Koch , M. ; Pierré , A. ; Guilbaud , N. ; Léonce , S. ; Kraus-Berthier , L. ; Rolland , Y. ; Atassi , G. Synthesis and cytotoxic and antitumor activity of esters in the 1,2-dihydroxy-1,2-dihydroacronycine series . J. Med. Chem. 1996 , 39 , 4762 – 4766 .
  • Magiatis , P. ; Mitaku , S. ; Skaltsounis , A.-L. ; Tillequin , F. ; Koch , M. ; Pierré , A. ; Atassi , G. Synthesis and cytotoxic activity of 1-alkoxy- and 1-amino-2-hydroxy-1,2-dihydroacronycine derivatives . Chem. Pharm. Bull. 1999 , 47 , 611 – 614 .
  • Majumdar , K. C. ; Taher , A. ; Ponra , S. Catalyst-free regioselective synthesis of benzopyran-annulated thiopyrano[2,3-b]thiochromen-5-(4H)-one derivatives by domino-Knoevenagel–hetero-Diels–Alder reaction of terminal alkynes with 4-hydroxy dithiocoumarin in aqueous medium . Tetrahedron Lett. 2010 , 51 ( 17 ), 2297 – 2300 .
  • Korotaev , V. Y. ; Sosnovskikh , V. Y. ; Barkov , A. Y. ; Slepukhin , P. A. ; Ezhikova , M. A. ; Kodess , M. I. ; Shklya , Y. V. A simple synthesis of the pentacyclic lamellarin skeleton from 3-nitro-2-(trifluoromethyl)-2H-chromenes and 1-methyl(benzyl)-3,4-dihydroisoquinolines . Tetrahedron 2011 , 67 ( 45 ), 8685 – 8698 .
  • Kammoun , M. ; Turki , H. ; Ammar , H. ; El Gharbi , R. Simple, efficient procedure for the synthesis of benzopyrano[2,3-c]isoxazoles. Synth. Commun. 2012, 11, 1677–1684.
  • Turki , H. ; Kammoun , M. ; Lehyani , S. ; El Gharbi , R. A simple efficient procedure for the synthesis of benzopyrano[2,3-c]pyrazoles . J. Heterocycl. Chem. in press.
  • 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 ( 19 ), 3553 – 3563 .
  • Kammoun , M. ; Turki , H. ; El Gharbi , R. ; Fery-Forgues , S. Reactivity of 3-cyano-nethoxycarbonyl-iminocoumarin with hydrazides as N-nucleophiles . J. Heterocycl. Chem. 2009 , 46 , 28 – 32 .
  • Kammoun , M. ; Turki , H. ; Fery-Forgues , S. ; El Gharbi , R. Convenient synthesis of a new series of 3-triazolonyl iminocoumarins . Synth. Commun. 2010 , 40 , 888 – 900 .
  • Maktouf , L. B. ; Kammoun , M. ; Ammar , H. ; Abid , S. Réactivité des 3-cyano iminocoumarines vis-à-vis du phénylsemicarbazide . Soc. Chim. Tunisie 2011 , 13 , 101 – 106 .
  • 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 .
  • Fakhfakh , M. ; Turki , H. ; Abid , S. ; El Gharbi , Fery-forgues , S. Preparation and optical properties of new fluorescent iminocoumarins: Study of N-acyl-derivatives . J. Photochem. Photobiol. A 2007 , 185 , 13 – 18 .
  • Shi , H. ; Zhang , T. ; Wang , H. ; Wang , X. ; He , M. Photocatalytic conversion of naphthalene to O-naphthol using nanometer-sized TiO2 . Chin. J. Catal. 2011 , 32 , 46 – 50 .

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