Synthesis 2015; 47(21): 3423-3433
DOI: 10.1055/s-0034-1378734
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Uracil-, Coumarin- and Quinolone-Fused Benzosultams and Benzosultones

Shovan Mondal*
Department of Chemistry, Visva-Bharati University, Santiniketan 731235, India   Email: shovan.mondal@visva-bharati.ac.in   Email: shovanku@gmail.com
,
Sudarshan Debnath
Department of Chemistry, Visva-Bharati University, Santiniketan 731235, India   Email: shovan.mondal@visva-bharati.ac.in   Email: shovanku@gmail.com
,
Subhajit Pal
Department of Chemistry, Visva-Bharati University, Santiniketan 731235, India   Email: shovan.mondal@visva-bharati.ac.in   Email: shovanku@gmail.com
,
Arko Das
Department of Chemistry, Visva-Bharati University, Santiniketan 731235, India   Email: shovan.mondal@visva-bharati.ac.in   Email: shovanku@gmail.com
› Author Affiliations
Further Information

Publication History

Received: 26 March 2015

Accepted after revision: 28 May 2015

Publication Date:
30 July 2015 (online)


Abstract

An efficient method for the regioselective synthesis of uracil-, coumarin- and quinolone-fused benzosultams and benzosultones is reported. The method offers a synthetic route to highly functionalized sultam and sultone derivatives in 75–95% yield under mild conditions. Density functional theory studies have been used to explain the regio­selectivity in the synthesis of the coumarin- and quinolone-fused sultams and sultones.

Supporting Information

 
  • References


    • For recent reviews on sultam chemistry, see:
    • 1a Majumdar KC, Mondal S. Chem. Rev. 2011; 111: 7749
    • 1b Scozzafava A, Owa T, Mastrolorenzo A, Supuran CT. Curr. Med. Chem. 2003; 10: 925
    • 1c McReynolds MD, Dougherty JM, Hanson PR. Chem. Rev. 2004; 104: 2239
    • 2a Miller RA, Humphrey GR, Lieberman DR, Ceglia SS, Kennedy DJ, Grabowski EJ. J, Reider PJ. J. Org. Chem. 2000; 65: 1399
    • 2b Katritzky AR, Wu J, Rachwal S, Rachwal B, Macomber DW, Smith TP. Org. Prep. Proced. Int. 1992; 24: 463
  • 3 Zia-ur-Rehman M, Choudary JA, Ahmad S, Siddiqui HL. Chem. Pharm. Bull. 2006; 54: 1175
  • 4 Valente C, Guedes RC, Moreira R, Iley J, Gut J, Rosenthal PJ. Bioorg. Med. Chem. Lett. 2006; 16: 4115
  • 5 Silvestri R, Marfe G, Artico M, La Regina G, Lavecchia A, Novellino E, Morgante M, Di Stefano C, Catalano G, Filomeni G, Abruzzese E, Ciriolo MR, Russo MA, Amadori S, Cirilli R, La Torre F, Sinibaldi Salimei P. J. Med. Chem. 2006; 49: 5840
  • 6 Lebegue N, Gallet S, Flouquet N, Carato P, Pfeiffer B, Renard P, Leonce S, Pierre A, Chavatte P, Berthelot P. J. Med. Chem. 2005; 48: 7363
  • 7 Francotte P, De Tullio P, Goffin E, Dintilhac G, Graindorge E, Fraikin P, Lestage P, Danober L, Thomas J.-Y, Caignard D.-H, Pirotte B. J. Med. Chem. 2007; 50: 3153
  • 8 Supuran CT. Nat. Rev. Drug Discovery 2008; 7: 168
  • 9 Inagaki M, Tsuri T, Jyoyama H, Ono T, Yamada K, Kobayashi M, Hori Y, Arimura A, Yasui K, Ohno K, Kakudo S, Koizumi K, Suzuki R, Kato M, Kawai S, Matsumoto S. J. Med. Chem. 2000; 43: 2040
  • 10 Brzozowski Z, Saczewski F, Neamati N. Bioorg. Med. Chem. Lett. 2006; 16: 5298
  • 11 Misu Y, Togo H. Org. Biomol. Chem. 2003; 1: 1342
  • 12 Wells GJ, Tao M, Josef KA, Bihovsky R. J. Med. Chem. 2001; 44: 3488
  • 13 Cherney RJ, Mo R, Meyer DT, Hardman KD, Liu R.-Q, Covington MB, Qian M, Wasserman ZR, Christ DD, Trzaskos JM, Newton RC, Decicco CP. J. Med. Chem. 2004; 47: 2981

    • For recent reviews on sultone chemistry, see:
    • 14a Mondal S. Chem. Rev. 2012; 112: 5339
    • 14b Metz P. J. Prakt. Chem. 1998; 340: 1
  • 15 Castro SD, García-Aparicio C, Andrei G, Snoeck R, Balzarini J, Camarasa MJ, Velázquez S. J. Med. Chem. 2009; 52: 1582
  • 16 Castro SD, Peromingo MT, Naesens L, Andrei G, Snoeck R, Balzarini J, Velázquez S, Camarasa MJ. J. Med. Chem. 2008; 51: 5823
  • 17 Rodríguez-Barrios F, Pérez C, Lobatón E, Velázquez S, Chamorro C, San-Félix A, Pérez-Pérez MJ, Camarasa MJ, Pelemans H, Balzarini J, Gago F. J. Med. Chem. 2001; 44: 1853
  • 18 Velázquez S, Lobatón E, De Clercq E, Koontz DL, Mellors JW, Balzarini J, Camarasa MJ. J. Med. Chem. 2004; 47: 3418
  • 19 Camarasa MJ, San-Félix A, Velázquez S, Pérez-Pérez MJ, Gago F, Balzarini J. Curr. Top. Med. Chem. 2004; 4: 945
  • 20 Castro SD, Lobatón E, Pérez-Pérez MJ, San-Félix A, Cordeiro A, Andrei G, Snoeck R, De Clercq E, Balzarini J, Camarasa MJ, Velázquez S. J. Med. Chem. 2005; 48: 1158
    • 21a Rajski SR, Williams RM. Chem. Rev. 1998; 98: 2723
    • 21b Murakami A, Gao G, Omura M, Yano M, Ito C, Furukawa H, Takahasi D, Koshimizu K, Ohigashi H. Bioorg. Med. Chem. Lett. 2000; 10: 59
    • 21c Grahner B, Winiwarter S, Lanzner W, Müller CE. J. Med. Chem. 1994; 37: 1526
  • 23 Liu XY, Li CH, Che CM. Org. Lett. 2006; 8: 2707
  • 24 Sherman ES, Chemler SR, Tan TB, Gerlits O. Org. Lett. 2004; 6: 1573
  • 25 Zeng W, Chemler SR. J. Am. Chem. Soc. 2007; 129: 12948
  • 26 Shi B, Merten S, Wong DK. Y, Chu JC. K, Liu LL, Lam SK, Jäger A, Wong WT, Chiu P, Metz P. Adv. Synth. Catal. 2009; 351: 3128
  • 27 Majumdar KC, Mondal S. Tetrahedron Lett. 2008; 49: 2418
  • 28 de Visser SP, Ogliaro F, Sharma PK, Shaik S. J. Am. Chem. Soc. 2002; 124: 11809
  • 29 Beletskaya IP, Cheprakov AV. Chem. Rev. 2000; 100: 3009
  • 30 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven TJ, Montgomery AJr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09. Gaussian Inc; Pittsburgh: 2009
  • 31 Becke AD. J. Chem. Phys. 1996; 104: 1040
  • 32 Hariharan PC, Pople JA. Theor. Chem. Acc. 1973; 28: 213
  • 33 Dunning TH. Jr, Hay PJ In Modern Theoretical Chemistry . Vol. 3. Schaefer HF. III. Plenum; New York: 1977: 1-28
  • 34 Tomasi J, Mennucci B, Cammi R. Chem. Rev. 2005; 105: 2999
    • 35a Fukui K. Acc. Chem. Res. 1981; 14: 363
    • 35b Hratchian HP, Schlegel HB In Theory and Applications of Computational Chemistry: The First 40 Years . Dykstra CE, Frenking G, Kim KS, Scuseria G. Elsevier; Amsterdam: 2005: 195-249