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Synthesis 2013; 45(9): 1247-1255
DOI: 10.1055/s-0032-1316891
DOI: 10.1055/s-0032-1316891
paper
The Direct Thiolation of Benzothiazole Catalyzed by Copper Complex in Superbase System
Further Information
Publication History
Received: 23 January 2013
Accepted after revision: 13 March 2013
Publication Date:
04 April 2013 (online)
Abstract
The copper-catalyzed direct thiolation of benzothiazole with iodobenzene and sulfur in superbase system under oxygen atmosphere is reported. The corresponding 2-thio-substituted benzothiazoles were formed in satisfactory yields.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1a Liu G, Huth J.-R, Olejniczak E.-T, Mendoza R, DeVries P, Leitza S, Reilly EB, Okasinski G.-F, Fesik S.-W, von Geldern T.-W. J. Med. Chem. 2001; 44: 1202
- 1b Nielsen S.-F, Nielsen E.-Ø, Olsen G.-M, Liljefors T, Peters D. J. Med. Chem. 2000; 43: 2217
-
1c Ley S.-V, Thomas A.-W. Angew. Chem. Int. Ed. 2003; 42: 5400
- 1d Hassan J, Sevignon M, Gozzi C, Schulz E, Lemaire M. Chem. Rev. 2002; 102: 1359
- 1e Beletskaya I.-P, Cheprakov A.-V. Coord. Chem. Rev. 2004; 248: 2337
- 1f Corbet J.-P, Mignani G. Chem. Rev. 2006; 106: 2651
- 1g Zhou Y, Liu W.-J, Ma Y, Wang H, Qi L, Cao Y, Wang J, Pei J. J. Am. Chem. Soc. 2007; 129: 12386
- 1h Mouri K, Wakamiya A, Yamada H, Kajiwara T, Yamaguchi S. Org. Lett. 2007; 9: 93
- 1i Stump B, Eberle C, Kaiser M, Brun R, Krauth-Siegel R.-L, Diederich F. Org. Biomol. Chem. 2008; 6: 3935
- 1j Pasquini S, Mugnaini C, Tintori C, Botta M, Trejos A, Arvela R.-K, Larhed M, Witvrouw M, Michiels M, Christ F, Debyser Z, Corelli F. J. Med. Chem. 2008; 51: 5125
- 1k Gangjee A, Zeng YB, Talreja T, McGuire J.-J, Kisliuk R.-L, Queener S.-F. J. Med. Chem. 2007; 50: 3046
- 1l De Martino G, Edler M.-C, La Regina G, Coluccia A, Barbera M.-C, Barrow D, Nicholson R.-I, Chiosis G, Brancale A, Hamel E, Artico M, Silvestri R. J. Med. Chem. 2006; 49: 947
- 2a Sidoova E, Odlerova Z, Volna F, Blockinger G. Chem. Zvesti. 1979; 33: 830 ; Chem. Abstr. 1980, 532411
- 2b Sutoris V, Foltinova P, Blockinger G. Chem. Zvesti. 1977; 31: 92 ; Chem. Abstr. 1978, 89573
- 2c Paramashivappa R, Kumar PP, Rao PV. S, Rao AS. Bioorg. Med. Chem. Lett. 2003; 13: 657
- 2d Zhang L, Fan J, Vu K, Hong K, Le Brazidec J.-Y, Shi J, Biamonte M, Busch D.-J, Lough R.-E, Grecko R, Ran Y, Sensintaffar J.-L, Kamal A, Lundgren K, Burrows F.-J, Mansfield R, Timony G.-A, Ulm EH, Kasibhatla S.-R, Boehm M.-F. J. Med. Chem. 2006; 40: 5352
- 2e Dumas J, Brittelli D, Chen J, Dixon B, Hatoum-Mokdad H, Konig G, Sibley R, Witowsky J, Wong S. Bioorg. Med. Chem. Lett. 1999; 9: 2531
- 2f Choudhary AN, Kumar A, Jural V. Mini-Rev. Med. Chem. 2010; 10: 705
- 2g Naya A, Kobayashi K, Ishikawa M, Ohwaki K, Saeki T, Noguchi K, Ohtake N. Bioorg. Med. Chem. Lett. 2001; 11: 1219
- 2h Greco M.-N, Hageman W.-E, Powell ET, Tighe J.-J, Persico F.-J. J. Med. Chem. 1992; 35: 3180
- 2i Waisser K, Sidoova E, Odlerova Z, Goeckeritz W, Drsata J. Pharmazie 1987; 42: 536
- 2j Franchini C, Muraglia M, Corbo F, Florio MA, Di Mola A, Rosato A, Matucci R, Nesi M, van Bambeke F, Vitali C. Arch. Pharm. (Weinheim, Ger.) 2009; 342: 605
- 3a Shi L, Liu X.-H, Zhang H, Jiang Y.-W, Ma D.-W. J. Org. Chem. 2011; 76: 4200
- 3b Murru S, Ghosh HK, Sahoo SK, Patel B. Org. Lett. 2009; 11: 4254
- 3c Murru S, Mondal P, Yella RK, Patel B. Eur. J. Org. Chem. 2009; 5406
- 3d Wang H.-F, Jiang L.-L, Chen T, Li Y.-M. Eur. J. Org. Chem. 2010; 2324
- 3e Feng Y.-S, Li Y.-Y, Tang L, Wu W, Xu H.-J. Tetrahedron Lett. 2010; 51: 2489
- 3f Niu L.-F, Cai Y, Liang C, Hui X.-P, Xu P.-F. Tetrahedron 2011; 67: 2878
- 3g Larsson P.-F, Correa A, Carril M, Norrby P.-O, Bolm C. Angew. Chem. Int. Ed. 2009; 48: 5691
- 3h Xu H.-J, Zhao Y.-Q, Feng T, Feng Y.-S. J. Org. Chem. 2012; 77: 2878
-
3i Bhadra S, Sreedhar B, Brindaban C, Ranu B. Adv. Synth. Catal. 2009; 351: 2369
- 3j Goriya Y, Ramana CV. Tetrahedron 2010; 66: 7642
- 3k Popov I, Do H.-Q, Daugulis O. J. Org. Chem. 2009; 74: 8309
- 3l Dai C, Xu Z.-Q, Huang F, Yu Z.-H, Gao Y.-F. J. Org. Chem. 2012; 77: 4414
- 3m Arisawa M, Toriyama F, Yamaguchi M. Tetrahedron Lett. 2011; 52: 2344
- 3n Li C.-L, Zhang X.-G, Tang R.-Y, Zhong P, Li J.-H. J. Org. Chem. 2010; 75: 7037
- 3o Ranjit S, Lee R, Heryadi D, Shen C, Wu J, Zhang P.-F, Huang K.-W, Liu X.-G. J. Org. Chem. 2011; 76: 8999
- 4 Han Y, Wang X.-H, Wang X.-W, Lv L.-Z, Diao G.-W, Yuan Y. Synthesis 2012; 44: 3207
-
5a Yuan Y, Thomé I, Kim S.-H, Chen D.-T, Beyer A, Bonnamour J, Zuidema E, Chang S, Bolm C. Adv. Synth. Catal. 2010; 352: 2892
- 5b Beyer A, Reucher C.-M.-M, Bolm C. Org. Lett. 2011; 13: 2876
- 5c Thomé I, Bolm C. Org. Lett. 2012; 14: 1892
- 5d Beyer A, Buendia J, Bolm C. Org. Lett. 2012; 14: 3948
- 5e Cano R, Ramén D.-J, Yus M. J. Org. Chem. 2011; 76: 654
- 6a Fukuzawa S.-I, Shimizu E, Atsuumi Y, Haga M, Ogata K. Tetrahedron Lett. 2009; 50: 2374
- 6b Higashi L.-S, Lundeen M, Hilti E, Seff K. Inorg. Chem. 1977; 16: 310
- 6c Zhang S.-H, Qian P.-C, Zhang M.-L, Hu M.-L, Cheng J. J. Org. Chem. 2010; 75: 6732
- 7 Correa A, Carril M, Bolm C. Angew. Chem. Int. Ed. 2008; 47: 2880