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Synlett 2010(5): 735-740  
DOI: 10.1055/s-0029-1219378
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Unusual Product from Condensative Cyclization: Pyrano[3,2-f]quinolin-3,10-diones from 6-Amino-5-[(trimethylsilyl)ethynyl]-2H-chromen-2-one and Aryl Aldehydes

K. C. Majumdar*, Abu Taher, Sudipta Ponra
Department of Chemistry, University of Kalyani, Kalyani 741235, WB, India
e-Mail: kcm_ku@yahoo.co.in;
Further Information

Publication History

Received 23 November 2009
Publication Date:
08 February 2010 (online)

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Abstract

A new efficient and simple route for the synthesis of 8,9-dihydro-3H-pyrano[3,2-f]quinoline-3,10(7H)-dione derivatives has been accomplished via sulfuric acid promoted condensation-­cyclization of 6-amino-5-[(trimethylsilyl)ethynyl]-2H-chromen-2-one and aromatic aldehydes. The products can be oxidized to the corresponding 10-methoxy-8-aryl-3H-pyrano[3,2-f]quinolin-3-one derivatives by FeCl3˙6H2O in methanol.

Key words

condensation-cyclization - 8,9-dihydro-3H-pyrano[3,2-f]-quinoline-3,10(7H)-dione - iron(III) chloride - 10-methoxy-8-phenyl-3H-pyrano[3,2-f]quinolin-3-one

    References and Notes

  • 1a Elderfield RC. In Heterocyclic Compounds   Vol. 4:  Elderfield RC. John Wiley; New York/London: 1960.  Chap. 1. p.1 
    Google Scholar
  • 1b Kournetsov VV. Mendez LYV. Gomez CMM. Curr. Org. Chem.  2005,  9:  141 
    Google Scholar
  • 1c Bringmann G. Reichert Y. Kane V. Tetrahedron  2004,  60:  3539 
    Google Scholar
  • 1d Sahu NS. Pal C. Mandal NB. Banerjee S. Raha M. Kundu AP. Basu A. Ghosh M. Roy K. Bandopadhyay S. Bioorg. Med. Chem.  2002,  10:  1687 
    Google Scholar
  • 1e Wright CW. Addac-Kyereme J. Breen AG. Brown JE. Cox MF. Croft SL. Gokeck Y. Kendrick H. Phillips RM. Pollet PL. J. Med. Chem.  2001,  44:  3187 
    Google Scholar
  • 2a Prakash O. Kumar D. Saini RK. Singh SP. Synth. Commun.  1994,  24:  2167 
    Google Scholar
  • 2b Singh OV. Kapil RS. Synth. Commun.  1993,  23:  277 
    Google Scholar
  • 2c Kalinin VN. Shostakovsky MV. Ponomaryov AB. Tetrahedron Lett.  1992,  33:  373 
    Google Scholar
  • 2d Xia Y. Yang Z.-Y. Xia P. Bastow KF. Tachibana Y. Kuo S.-C. Hamel E. Hackl T. Lee K.-H. J. Med. Chem.  1998,  41:  1155 
    Google Scholar
  • 3 Antimalarial Drugs II   Peters W. Richards WHG. Springer; Berlin: 1984. 
    Google Scholar
  • 4a Maguire MP. Sheets KR. McVety K. Spada AP. Zilberstein A. J. Med. Chem.  1994,  37:  2129 
    Google Scholar
  • 4b Kalluraya B. Sreenivasa S. Farmaco  1998,  53:  399 
    Google Scholar
  • 4c Dube D. Blouin M. Brideau C. Chan C.-C. Desmarais S. Ethier D. Falgueyret J.-P. Friesen RW. Girard M. Girard Y. Guay J. Riendeau D. Tagari P. Young RN. Bioorg. Med. Chem. Lett.  1998,  8:  1255 
    Google Scholar
  • 4d Roma G. Braccio MD. Grossi G. Mattioli F. Ghia H. Eur. J. Med. Chem.  2000,  35:  1021 
    Google Scholar
  • 4e Benkovic SJ. Baker SJ. Alley MRK. Woo Y.-H. Zhang Y.-K. Akama T. Mao W. Baboval J. Rajagopalan PTR. Wall M. Kahng LS. Tavassoli A. Shapiro L. J. Med. Chem.  2005,  48:  7468 
    Google Scholar
  • 4f Vargas LY. Castelli MV. Kouznetsov VV. Urbina JM. Lopez SN. Sortino M. Enriz RD. Ribas JC. Zacchino S. Bioorg. Med. Chem.  2003,  11:  1531 
    Google Scholar
  • 4g Dassonneville L. Bonjean K. De Pauw-Gillet M.-C. Colson P. Houssier C. Quetin-Leclercq J. Angenot L. Ablordeppey SY. Bioorg. Med. Chem.  2002,  10:  1337 
    Google Scholar
  • 5a Goodwin S. Smith AF. Valsquez AA. Horning EC. J. Am. Chem. Soc.  1959,  81:  6209 
    Google Scholar
  • 5b Fournet A. Vagneur B. Rilchomme P. Bruneton J. Can. J. Chem.  1989,  67:  2116 
    Google Scholar
  • 6 Ko T.-C. Hour M.-J. Lien J.-C. Teng C.-M. Lee K.-H. Kuo S.-C. Huang L.-J. Bioorg. Med. Chem. Lett.  2001,  11:  279 
    CrossrefGoogle Scholar
  • 7a Michael JP. Nat. Prod. Rep.  2000,  17:  603 
    Google Scholar
  • 7b Michael JP. Nat. Prod. Rep.  2004,  21:  650 
    Google Scholar
  • 8a Marco JL. Carreiras MC. J. Med. Chem.  2003,  6:  518 
    Google Scholar
  • 8b Puricelli L. Innocenti G. Delle Monache G. Caniato R. Filippini R. Cappelletti EM. Nat. Prod. Lett.  2002,  16:  95 
    Google Scholar
  • 8c Corral RA. Orazi OO. Tetrahedron Lett.  1967,  7:  583 
    Google Scholar
  • 8d Sekar M. Rejendra Prasad KJ. J. Nat. Prod.  1998,  61:  294 
    Google Scholar
  • 9a Donnelly JA. Farrell DF. Tetrahedron  1990,  46:  885 
    Google Scholar
  • 9b Donnelly JA. Farrell DF. J. Org. Chem.  1990,  55:  1757 
    Google Scholar
  • 9c Tokes AL. Litkei G. Synth. Commun.  1993,  23:  895 
    Google Scholar
  • 9d Varma RS. Sani RK. Synlett  1997,  857 
    Google Scholar
  • 9e Kumar KH. Muralidharan D. Perumal PT. Synthesis  2004,  63 
    Google Scholar
  • 9f Ahmed N. van Lier JE. Tetrahedron Lett.  2006,  47:  2725 
    Google Scholar
  • 9g Ahmed N. van Lier JE. Tetrahedron Lett.  2007,  48:  13 
    Google Scholar
  • 9h Kumar KH. Perumal PT. Can. J. Chem.  2006,  84:  1079 
    Google Scholar
  • 9i Chandrasekhar S. Vijeender K. Sridhar C. Tetrahedron Lett.  2007,  48:  4935 
    Google Scholar
  • 9j Kumar D. Patel G. Kumar A. Roy RK. J. Heterocycl. Chem.  2009,  46:  791 
    Google Scholar
  • 10a Singh OV. Kapil RS. Synlett  1992,  751 
    Google Scholar
  • 10b Verma RS. Kumar D. Tetrahedron Lett.  1998,  39:  9113 
    Google Scholar
  • 10c Mphahlele MJ. Mogamisi FK. Tsanwani M. Hlatshwayo MS. Mampa MR. J. Chem. Res., Synop.  1999,  706 
    Google Scholar
  • 10d Arcadi A. Marinelli F. Rossi E. Tetrahedron  1999,  55:  13233 
    Google Scholar
  • 10e Kumar KH. Perumal PT. Tetrahedron  2007,  63:  9531 
    Google Scholar
  • 10f Kumar KH. Muralidharan D. Perumal PT. Tetrahedron Lett.  2004,  45:  7903 
    Google Scholar
  • 10g Wang Y. Peng C. Liu L. Zhao J. Su L. Zhu Q. Tetrahedron Lett.  2009,  50:  2261 
    Google Scholar
  • 11a Goodwin S. Smith AF. Horning EC. J. Am. Chem. Soc.  1957,  79:  2239 
    Google Scholar
  • 11b Elderfield EC. White JB. J. Am. Chem. Soc.  1946,  68:  1276 
    Google Scholar
  • 12a Tokes AL. Szilagyi L. Synth. Commun.  1987,  17:  1235 
    Google Scholar
  • 12b Tokes AL. Litkei G. Szilagyi L. Synth. Commun.  1992,  22:  2433 
    Google Scholar
  • 13a Singh OV. Kapil RS. Synlett  1992,  751 
    Google Scholar
  • 13b Varma RS. Kumar D. Tetrahedron Lett.  1998,  39:  9113 
    Google Scholar
  • 14a Majumdar KC. Taher A. Debnath P. Synthesis  2009,  793 
    Google Scholar
  • 14b Majumdar KC. Chattopadhyay B. Taher A. Synthesis  2007,  3647 
    Google Scholar
  • 14c Majumdar KC. Debnath P. Taher A. Lett. Org. Chem.  2008,  5:  169 
    Google Scholar
  • 15 Majumdar KC. Mondal S. Tetrahedron Lett.  2008,  49:  2418 
    CrossrefGoogle Scholar
16

General Procedure for the Preparation of Compound 5a A mixture of 6-amino-5-[(trimethylsilyl)ethynyl]-2H-chromen-2-one (3, 50 mg, 0.194 mmol), benzaldehyde (4a, 21 mg, 0.194 mmol) and concd H2SO4 (19 mg, 0.194 mmol) was refluxed in MeOH for 2.5 h. After completion of the reaction as monitored by TLC, the reaction mixture was cooled, and the solvent was removed under vacuum and diluted with H2O (50 mL). The mixture was extracted with EtOAc (3 × 25 mL). The combined organic extract was washed with a sat. solution of NaHCO3, followed by brine solution, and dried over anhyd Na2SO4. The solvent was distilled off. The crude product was purified by column chromatography over silica gel (60-120 mesh) using PE-EtOAc (75:25) mixture as eluent to give 8-phenyl-8,9-dihydro-3H-pyrano[3,2-f]quinoline-3,10 (7H)-dione (5a); yield 77%, orange color solid; mp 160-162 ˚C. IR (KBr): νmax = 1299, 1656, 1713, 3318 cm-¹. ¹H NMR (400 MHz, CDCl3): δ = 2.72-2.78 (m, 1 H), 2.87 (dd, J = 14.0, 16.0 Hz, 1 H), 4.69 (s, 1 H), 4.71 (dd, J = 4.0, 14.0 Hz, 1 H), 6.41 (d, J = 10.0 Hz, 1 H), 6.83 (d, J = 9.2 Hz, 1 H), 7.25 (d, J = 9.2 Hz, 1 H), 7.28-7.40 (m, 5 H), 9.28 (d, J = 10.0 Hz, 1 H) ppm. ¹³C NMR (100 MHz): δ = 47.1, 58.0, 110.7, 117.8, 118.2, 120.9, 124.4, 126.5, 128.7, 129.1, 140.0, 142.1, 148.0, 150.1, 160.3, 194.3 ppm. MS: m/z = 292.1 [M + H]+. Anal. Calcd (%) for C18H13NO3: C, 74.22; H, 4.50; N, 4.81. Found: C, 74.49; H, 4.43; N, 4.70.

17

General Procedure for the Preparation of Compound 6a A solution of 8-phenyl-8,9-dihydro-3H-pyrano[3,2-f]quinoline-3,10 (7H)-dione (5a, 50 mg, 0.172 mmol) in MeOH (15 mL), FeCl3˙6H2O (116 mg, 0.430 mmol) was added, and the mixture was refluxed on a water bath for 4 h. After completion of the reaction as monitored by TLC, the reaction mixture was cooled and diluted with H2O (50 mL). This was extracted with EtOAc (3 × 25 mL). The combined organic extract was washed with brine solution and dried over anhyd Na2SO4. The solvent was distilled off. The resulting crude product was purified by column chromatog-raphy over silica gel (60-120 mesh) using PE-EtOAc mixture (1:1) as eluent to give 10-methoxy-8-phenyl-3H-pyrano[3,2-f]quinolin-3-one (6a); yield 99%; pale yellow solid; mp 224-226 ˚C. IR (KBr): νmax = 1297, 1563, 1704, 3356 cm-¹. ¹H NMR (400 MHz, CDCl3): δ = 4.22 (s, 3 H), 6.52 (d, J = 10.0 Hz, 1 H), 7.40 (s, 1 H), 7.47-7.57 (m, 3 H), 7.67 (d, J = 9.2 Hz, 1 H), 8.12-8.15 (m, 2 H), 8.26 (d, J = 9.6 Hz, 1 H), 9.31 (d, J = 10.0 Hz, 1 H) ppm. ¹³C NMR (100 MHz, CDCl3): δ = 55.9, 100.7, 113.1, 115.2, 115.4, 121.0, 127.3, 128.9, 129.7, 134.7, 139.0, 143.8, 147.5, 153.9, 158.1, 160.3, 164.3 ppm. HRMS: m/z calcd for C19H13NO3 [M + H]+: 304.0968; found: 304.0938.