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

Shovan Mondal; Sudarshan Debnath; Subhajit Pal; Arko Das

doi:10.1055/s-0034-1378734

Synthesis, Table of Contents

Synthesis 2015; 47(21): 3423-3433
DOI: 10.1055/s-0034-1378734

paper

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

Abstract

All articles of this category

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.

Key words

sultams - sultones - regioselectivity - density functional theory

Full Text

References

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

22a Mondal S, Debnath S. Tetrahedron Lett. 2014; 55: 1577
22b Mondal S, Debnath S. Synthesis 2014; 46: 368

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

Supplementary Material

Supporting Information