Subscribe to RSS
DOI: 10.1055/s-2008-1067115
Synthesis of Sulfonamides and 1,3-Oxazine-2,4-diones from Arylsulfonyl Isocyanates and Diketene
Publication History
Publication Date:
11 June 2008 (online)
Abstract
An effective route to functionalized N 1-[(2,6-dimethyl-4-oxo-4H-pyran-3-yl)carbonyl]-1-arylsulfonamide and 3-(arylsulfonyl)-6-methyl-2H-1,3-oxazine-2,4(3H)-dione derivatives is described. This involves the reaction of arylsulfonyl isocyanates and diketene in the presence of N-heteroaromatic compounds such as 1,3,5-triazine, 1-methyl-1H-imidazole, or pyridine as catalyst. The reactive 1:1 zwitterions obtained from the addition of N-heteroaromatic compound to arylsulfonyl isocyanates were trapped by diketene to produce functionalized sulfonamide and 1,3-oxazine-2,4(3H)-dione derivatives.
Key words
arylsulfonyl isocyanate - catalytic reaction - diketene - N-heteroaromatic compounds - sulfonamides - zwitterions
- 1
Navia MA. Science 2000, 288: 2132 - 2
Mohamed SK. Afinidad 2000, 57: 451 ; Chem. Abstr. 2000, 133, 73818x - 3
Maren TH.Conroy CW. J. Biol. Chem. 1993, 268: 26233 - 4
Scozzafava A.Owa T.Mastrolorenzo A.Supuran CT. Curr. Med. Chem. 2003, 10: 925 - 5
Owa T.Yoshino H.Okauchi T.Yoshimatsu K.Ozawa Y.Sugi NH.Nagasu T.Koyanagi N.Kitoh K. J. Med. Chem. 1999, 42: 3789 - 6
Koyanagi N.Nagasu T.Fujita F.Watanabe T.Tsukahara K.Funahashi Y.Fujita M.Taguchi T.Yoshino H.Kitoh K. Cancer Res. 1994, 54: 1702 -
7a
Roush WR.Gwaltney SL.Cheng J.Scheidt KA.McKerrow JH.Hansell E. J. Am. Chem. Soc. 1998, 120: 10994 -
7b
Roush WR.Cheng J.Knapp-Reed B.Alvarez-Hernandez A.McKerrow JH.Hansell E.Engel JC. Bioorg. Med. Chem. Lett. 2001, 11: 2759 -
7c
Maren TH. Annu. Rev. Pharmacol. Toxicol. 1976, 16: 309 -
7d
Supuran CT.Briganti F.Tilli S.Chegwidden WR.Scozzafava A. Bioorg. Med. Chem. 2001, 9: 703 -
7e
Scozzafava A.Menabuoni L.Mincione F.Briganti F.Mincione G.Supuran CT. J. Med. Chem. 2000, 43: 4542 -
8a
Yokoi A.Kuromitsu J.Kawai T.Nagasu T.Sugi NH.Yoshimatsu K.Yoshino H.Owa T. Mol. Cancer Ther. 2002, 1: 275 -
8b
Oda Y.Owa T.Sato T.Boucher B.Daniels S.Yamanaka H.Shinohara Y.Yokoi A.Kuromitsu J.Nagasu T. Anal. Chem. 2003, 75: 2159 -
8c
Owa T.Yokoi A.Yamazaki K.Yoshimatsu K.Yamori T.Nagasu T. J. Med. Chem. 2002, 45: 4913 -
8d
Owa T.Okauchi T.Yoshimatsu K.Sugi NH.Ozawa Y.Nagasu T.Koyanagi N.Okabe T.Kitoh K.Yoshino H. Bioorg. Med. Chem. Lett. 2000, 10: 1223 - 9
Huang S.Connolly PJ.Lin R.Emanuel S.Middleton SA. Bioorg. Med. Chem. Lett. 2006, 16: 3639 -
10a
Staunton J. In Comprehensive Organic Chemistry Vol. 4:Barton DHR.Ollis WD. Pergamon Press; Oxford: 1979. p.679 -
10b See also:
Staunton J. In Comprehensive Organic Chemistry Vol. 4:Barton DHR.Ollis WD. Pergamon Press; Oxford: 1979. p.688 -
11a See also:
Ellis GP. In The Chemistry of Heterocyclic Compounds Chromenes, Chromanones and Chromones Vol. 31:Weissberger A.Taylor EC. Wiley; New York: 1977. p.912 -
11b
Ellis GP. In The Chemistry of Heterocyclic Compounds Chromenes, Chromanones and Chromones Vol. 31:Weissberger A.Taylor EC. Wiley; New York: 1977. p.985 -
11c
Ellis GP. In The Chemistry of Heterocyclic Compounds Chromenes, Chromanones and Chromones Vol. 31:Weissberger A.Taylor EC. Wiley; New York: 1977. p.1063 -
12a
Kato Y. Food Sci. Technol. Res. 2003, 9: 264 -
12b
Yanagimoto K.Ochi H.Lee KG.Shibamoto T. J. Agric. Food Chem. 2004, 52: 592 -
13a
Caravan P.Gelmini L.Glover N.Herring FG.McNeill H.Li JH.Rettig SJ.Setyawati IA.Shuter E.Sun Y.Tracey AS.Yuen VG.Orvig C. J. Am. Chem. Soc. 1995, 117: 12759 -
13b
Reffitt DM.Burden TJ.Seed PT.Wood J.Thompson RPH.Powell JJ. Ann. Clin. Biochem. 2000, 37: 457 -
13c
Johnson VJ.Sharma RP. Neurotoxicology 2003, 24: 261 -
13d
Hinds FE.Aldrich-Wright JR.Leverett P.Hazell SL. J. Inorg. Biochem. 2003, 96: 144 -
13e
Ellis BL.Duhme AK.Hider RC.Hossian MB.Rizvi S.van der Helm D. J. Med. Chem. 1996, 39: 3659 -
14a
Clauson-Kaas N,Denss R,Ostermayer F, andRenk E. inventors; J. R. Geigy A.G., Swiss Appl. 1339175. ; Chem. Abstr. 1964, 60, 4158d -
14b
Clauson-Kaas N,Denss R,Ostermayer F, andRenk E. inventors; J. R. Geigy A.G. Swiss Appl. 419160. ; Chem. Abstr. 1967, 66, 115718v -
15a
Coppola GM. Synthesis 1980, 503 -
15b
Coppola GM.Marsden CM. Heterocycl. Commun. 1996, 2: 301 -
16a
Kawai M.BaMaung NY.Fidanze SD.Erickson SA.Tedrow JS.Sanders WJ.Vasudevan A.Park C.Hutchins C.Comess KM.Kalvin D.Wang J.Zhang Q.Lou P.Tucker-Garcia L.Bouska J.Bell RL.Lesniewski R.Henkin J.Sheppard GS. Bioorg. Med. Chem. Lett. 2006, 16: 3574 -
16b
Siddiqui N.Pandeya SN. Bioorg. Med. Chem. Lett. 2007, 17: 255 -
16c
Johnson DC.Widlanski TS. Tetrahedron Lett. 2001, 42: 3677 -
16d
Vogel A. Textbook of Practical Organic Chemistry Longman; London: 1978. 4th ed.. p.647 -
16e
Cremlyn R. Organosulfur Chemistry: An Introduction Wiley; New York: 1996. -
16f
Anderson KK. Sulfonic Acids and Their Derivatives, In Comprehensive Organic Chemistry Vol. 3:Barton DHR.Ollis WD.Jones DN. Pergamon Press; Oxford: 1979. -
16g
Domínguez JN.León C.Rodrigues J.Domínguez N.Gut J.Rosenthal P. Farmaco 2005, 60: 307 -
16h
Murakami Y.Kondo K.Sekimoto E.Nakao J. Tetrahedron 2000, 56: 5843 -
16i
Ito Y.Manabe S.Sugioka T. Tetrahedron Lett. 2007, 48: 787 -
16j
Alizadeh A.Rostamnia S.Esmaili A. Synthesis 2007, 709 -
17a
Bartol G.Bosco M.Cimarreli C.Dalpozo R.Guereio G.Palmieri G. J. Chem. Soc., Perkin Trans. 1 1993, 2081 -
17b
Yamamoto Y.Morita Y. Chem. Pharm. Bull. 1984, 32: 2957 -
17c
Majetich G.Zhanj Y.Dreger G. Tetrahedron Lett. 1993, 34: 449 -
17d
Ficini J.Pouliquen J. Tetrahedron Lett. 1972, 1135 -
17e
Sano T.Saitoh T. Heterocycles 1993, 36: 2139 -
17f
Kim HS.Yoon YH. Bull. Korean Chem. Soc. 1993, 14: 159 -
17g
Andrey Chicov YS.Vinokurova OV.Gein VL. Chem. Heterocycl. Compd. (English Trans.) 1989, 126 -
17h
Weeks PD.Brennan TM.Brannegan TD.Kuhla DE.Elliott ML.Watson HA. J. Org. Chem. 1980, 45: 1109 -
17i
Grrige R.Jachson GL. J. Chem. Soc. C 1970, 552 -
17j
Harris TM.Wachter MP. Tetrahedron 1970, 26: 5255 -
18a
Clauson-Kaas N,Denss R,Ostermayer F, andRenk E. inventors; J. R. Geigy A.G., Swiss Appl. 436323. ; Chem. Abstr. 1968, 69, 27435g -
18b
Clauson-Kaas N,Denss R,Ostermayer F, andRenk E. inventors; J. R. Geigy A.G., Swiss Appl. 412 602. ; Chem. Abstr. 1967, 67: 11492w - 19
Huisgen R.Herbig K.Morikawa M. Chem. Ber. 1967, 100: 1107 - 20
Ulrich H. Chem. Rev. 1962, 2: 186 - 21
Adib M.Yavari H.Mollahosseini M. Tetrahedron Lett. 2004, 45: 1803 - 22
Ozaki Sh. Chem. Rev. 1972, 72: 457 - 23
Alizadeh A.Zohreh N.Rostamnia S. Tetrahedron 2007, 63: 8083 - 24
Mansson M.Nakase Y.Sunner S. Acta Chem. Scand. 1968, 22: 171 - 25
Briody JM.Satchell DPN. J. Chem. Soc. 1965, 3778 - 26
Briody JM.Satchell DPN. Chem. Ind. (London) 1964, 893 - 27
Eck H. inventors; Wacker Chemie GmbH, Br. Patent 1346701. ; Chem. Abstr. 1973, 79, 18109 - 28
Marcus E.Chan JK.Strow CB. J. Org. Chem. 1966, 31: 1369 -
29a
Pochan M. inventors; Lonza Ltd., Swiss Patent 523223. ; Chem. Abstr. 1972, 77, 100857 -
29b
Stocker A. inventors; Lonza, US Patent 3778474. ; Chem. Abstr. 1974, 80, 59503 -
29c
Kunstle G,Spes H, andSiegl H. inventors; Wacker-Chemie GmbH, U.S. Patent 4129596. ; Chem. Abstr. 1978, 89, 42479f
References
Crystallographic data for 5a have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 642465. Copies of the data may be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44 1223 33603 or e-mail: deposit@ccdc.cam.ac.uk).