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Synlett 2011(16): 2369-2373  
DOI: 10.1055/s-0030-1260312
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed One-Pot Synthesis of Pyrrole-Annulated Coumarin, Quinolone, and 7-Aza-indole Derivatives

K. C. Majumdar*a,b, Sintu Ganaia, Buddhadeb Chattopadhyaya, Krishanu Raya
a Department of Chemistry, University of Kalyani, Kalyani 741235, West Bengal, India
b Department of Chemical Sciences, Tezpur University, Napaam, Tezpur 784028, India
Fax: +91(33)25828282; e-Mail: kcm_ku@yahoo.co.in;
Further Information

Publication History

Received 9 June 2011
Publication Date:
13 September 2011 (online)

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Abstract

An efficient one-pot approach for the synthesis of highly substituted pyrrolocoumarin, quinolone, and pyrrolopyridine derivatives has been achieved by palladium acetate catalyzed reaction in DMF through initially formed enamine from cyclic and acyclic ketones and 6-amino-5-bromocoumarin, 6-amino-5-bromo-1-methyl quinolone, and 2-amino-3,5-dibromopyridine, respectively.

Key words

pyrrolocoumarin - pyrroloquinolone - pyrrolopyridine - palladium acetate

    References and Notes

  • 1a Boyd DR. Sharma ND. Barr SA. Carroll JG. Mackerracher D. Malone JF. J. Chem. Soc., Perkin Trans. 1  2000,  3397 
    Google Scholar
  • 1b Bar G. Parsons AF. Thomas CB. Tetrahedron  2001,  57:  4719 
    Google Scholar
  • 1c Lee YR. Kim BS. Kweon HI. Tetrahedron  2000,  56:  3867 
    Google Scholar
  • 1d Pirrung MC. Blume F. J. Org. Chem.  1999,  64:  36-42  
    Google Scholar
  • 1e Dickinson JM. Nat. Prod. Rep.  1993,  10:  71 
    Google Scholar
  • 2 Jiang W. Alford VC. Qiu Y. Bhattacharjee S. John TM. Johnson DH. Kraft PJ. Lundeen SG. Sui Z. Bioorg. Med. Chem.  2004,  12:  1505 
    CrossrefGoogle Scholar
  • 3 Yamashkin SA. Yudin LG. Kost AN. Chem. Heterocycl. Compd. (Engl. Transl.)  1983,  19:  401 
    CrossrefGoogle Scholar
  • 4 Kontogiorgis C. Litinas KE. Makri A. Nicolaides DN. Vronteli A. Litina DJH. Pontiki E. Siohou A. J. Enzyme Inhib. Med. Chem.  2008,  23:  43 
    CrossrefPubMedGoogle Scholar
  • 5 Rodighiero P. Chilin A. Pastorini G. Guiotto A. J. Heterocycl. Chem.  1987,  24:  1041 
    CrossrefGoogle Scholar
  • 6 Guiotto A. Chilin A. Manzini P. Dall’Acqua F. Bordin F. Rodighiero P. Farmaco  1995,  50:  479 
    PubMedGoogle Scholar
  • 7 Gia O. Mobilio S. Chilin A. Rodghiero P. Palumbo M. J. Photochem. Photobiol., B.  1988,  2:  435 
    CrossrefGoogle Scholar
  • 8 Quanten E. Adriaens P. Schryver FC. Roelandts R. Degreef H. Photochem. Photobiol.  1986,  43:  485 
    CrossrefGoogle Scholar
  • 9 Kontogiorgis C. Litinas KE. Makri A. Nicolaides DN. Vronteli A. Litina DJH. Pontiki E. Siohou A. J. Enzyme Inhib. Med. Chem.  2008,  23:  43 
    CrossrefPubMedGoogle Scholar
  • 10 Chen L. Hu T.-S. Yao Z.-J. Eur. J. Org. Chem.  2008,  6175 
    Google Scholar
  • 11 Chen L. Xu MH. Adv. Synth. Catal.  2009,  351:  2005 
    CrossrefGoogle Scholar
  • 12a Ridley CP. Reddy MVR. Rocha G. Bushman FD. Faulknera DJ. Bioorg. Med. Chem.  2002,  10:  3285 
    Google Scholar
  • 12b Fan H. Peng J. Hamann MT. Hu JH. Chem. Rev.  2008,  108:  264 
    Google Scholar
  • 12c Yamaguchi T. Fukuda T. Ishibashi F. Iwao M. Tetrahedron Lett.  2006,  47:  3755 
    Google Scholar
  • 12d Tardy C. Facompré M. Laine W. Baldeyrou B. García-Gravalos D. Francesch A. Mateo C. Pastor A. Jiménez JA. Manzanares I. Cuevasb C. Bailly C. Bioorg. Med. Chem.  2004,  12:  1697 
    Google Scholar
  • 13 Hiremath SP. Badiger GR. Jivanagi AS. Purohit MG. Indian J. Chem.  1992,  313:  583 
    Google Scholar
  • 14a Kuethe JT. Wong A. Qu C. Smitrovich J. Davies IW. Hughes DL. J. Org. Chem.  2005,  70:  2555 
    Google Scholar
  • 14b Van Zandt MC. Jones ML. Gunn DE. Geraci LS. Jones JH. Sawicki DR. Sredy J. Jacot JL. Dicioccio AT. Petrova T. Mitschler A. Podjarny AD. J. Med. Chem.  2005,  48:  3141 
    Google Scholar
  • 14c Faulkner D. J. Nat. Prod. Rep.  1999,  16:  155 
    Google Scholar
  • 14d Lounasmaa M. Tolvanen A. Nat. Prod. Rep.  2000,  17:  175 
    Google Scholar
  • 15a Henry JR. Rupert KC. Dodd JH. Turchi IJ. Wadsworth SA. Cavender DE. Fahmy B. Olini GC. Davis JE. Pellegrino-Gensey JL. Schafer PH. Siekierka JJ. J. Med. Chem.  1998,  41:  4196 
    Google Scholar
  • 15b Henry JR. Rupert KC. Dodd JH. Turchi IJ. Wadsworth SA. Cavender DE. Schafer PH. Siekierka J. J. Bioorg. Med. Chem. Lett.  1998,  8:  3335 
    Google Scholar
  • 16 Peter AN, Thomas B, Anna K, Tero L, and Peter S. inventors; WO  2004016609.  ; Chem. Abstr. 2004, 140, 217627
  • 17 Majumdar KC. Chattopadhyay B. Synthesis  2008,  921 
    Article in Thieme ConnectGoogle Scholar
  • 18 Majumdar KC. Chattopadhyay B. Samanta S. Synthesis  2008,  311 
    Article in Thieme ConnectGoogle Scholar
  • 19 Majumdar KC. Chakravorty S. Shyam PK. Taher A. Synthesis  2009,  403 
    Article in Thieme ConnectGoogle Scholar
  • 20 Majumdar KC. Mondal S. Tetrahedron Lett.  2009,  49:  2418 
    Google Scholar
  • 21 Chen C.-Y. Lieberman DR. Larsen DR. Verhoeven TR. Reider PJ. J. Org. Chem.  1997,  62:  2676 
    CrossrefGoogle Scholar
  • 23a Rodriguez AL. Koradin C. Dohle W. Knochel P. Angew. Chem. Int. Ed.  2000,  39:  2488 
    Google Scholar
  • 23b Koradin C. Dohle W. Rodriguez AL. Schmid B. Knochel P. Tetrahedron  2003,  59:  1571 
    Google Scholar
  • 23c Amjad M. Knight DW. Tetrahedron Lett.  2004,  45:  539 
    Google Scholar
  • 23d Cacchi S. Fabrizi G. Parisi LM. J. Comb. Chem.  2005,  7:  510 
    Google Scholar
  • 23e Nazaré M. Schneider C. Lindenschmidt A. Will DW. Angew. Chem. Int. Ed.  2004,  43:  4256 
    Google Scholar
  • 23f Roy PJ. Dufresne C. Lachance N. Leclerc J.-P. Boisvert M. Wang Z. Leblanc Y. Synthesis  2005,  2751 
    Google Scholar
  • 24 Blache Y. Sinibaldi-Troin M.-E. Hichour M. Benezech V. Chavignon O. Gramain J.-C. Teulade J.-C. Chapat J.-P. Tetrahedron  1999,  55:  1959 
    CrossrefGoogle Scholar
  • 25 Lachance N. April M. Joly M.-A. Synthesis  2005,  2571 
    Article in Thieme ConnectGoogle Scholar
  • 26 Xu Z. Hu W. Zhang F. Li Q. Lu Z. Zhang L. Jia Y. Synthesis  2008,  3981 
    Article in Thieme ConnectGoogle Scholar
  • 27 Spergel SH. Danielle R. Okoro DR. Pitts W. J. Org. Chem.  2010,  75:  5316 
    CrossrefPubMedGoogle Scholar
22

General Procedure for the Synthesis of Compound 3a by Heck Reaction A mixture of 1a (100 mg, 0.395 mmol), cyclohexanone (2a, 77.5 mg, 0.79 mmol), and DABCO (132.7 mg, 1.185 mmol) was taken in DMF (5 mL) under nitrogen atmosphere. Pd(OAc)2 (10 mol%, 8.8 mg) was added and the reaction mixture was stirred at 120 ˚C for 4 h. After completion of the reaction as monitored by TLC, the reaction mixture was cooled, H2O (20 mL) was added and extracted with EtOAc (3 × 30 mL). The EtOAc extract was washed with H2O (2 × 40 mL), followed by brine (30 mL). The organic layer was dried (Na2SO4), and the solvent was evaporated to give a crude product which was purified by column chromatog-raphy over silica gel (230-400 mesh) using PE-EtOAc (3:2) as eluent. Product 3a was isolated as a white solid in 91% yield. Compound 3a
Yield 91%, solid, mp 254-256 ˚C. IR (KBr): 1637, 3305 cm-¹. ¹H NMR (400 MHz, CDCl3): δ = 8.30 (d, 1 H, J = 9.5 Hz), 8.00 (s, 1 H), 7.48 (d, 1 H, J = 9.0 Hz), 7.13 (d, 1 H, J = 9.0 Hz), 6.73 (d, 1 H, J = 9.5 Hz), 3.80 (s, 3 H), 3.00 (br s, 2 H), 2.80 (br s, 2 H), 1.93 (br s, 4 H). ¹³C NMR (100 MHz, DMSO): δ = 22.17, 23.13, 23.18, 23.41, 29.57, 107.28, 108.69, 112.51, 114.75, 118.38, 122.47, 130.57, 134.79, 135.60, 136.82, 160.65; MS: m/z = 253 [M+ + H]. Anal. Calcd for C16H16N2O: C, 76.16; H, 6.39; N, 11.10. Found: C, 76.34, H, 6.42, N, 11.27.