RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
PDF herunterladen
Synlett 2013; 24(4): 465-470
DOI: 10.1055/s-0032-1318158
DOI: 10.1055/s-0032-1318158
letter
Eosin Y Catalyzed Visible-Light-Driven Aerobic Oxidative Cyclization of Thioamides to 1,2,4-Thiadiazoles
Authors
Weitere Informationen
Publikationsverlauf
Received: 06. Dezember 2012
Accepted after revision: 14. Januar 2013
Publikationsdatum:
06. Februar 2013 (online)
Abstract
A new approach for an efficient metal-free synthesis of 1,2,4-thiadiazoles from primary thioamides using visible light and air in the presence of eosin Y as a photoredox catalyst is reported. The protocol involves an aerobic oxidative cyclization of thioamides via the formation of C–N and C–S bonds to afford excellent yields of the products in a simple one-pot operation under mild conditions.
-
References and Notes
- 1a Tucker JW, Stephenson CR. J. J. Org. Chem. 2012; 77: 1617
- 1b Narayanam JM. R, Stephenson CR. J. Chem. Soc. Rev. 2011; 40: 102
Reference Ris Wihthout Link
- 1c Teply F. Collect. Czech. Chem. Commun. 2011; 76: 859
- 1d Yoon TP, Ischay MA, Du JN. Nat. Chem. 2010; 2: 527
Reference Ris Wihthout Link
- 1e Zeitler K. Angew. Chem. Int. Ed. 2009; 48: 9785
- 1f Xuan J, Xiao W.-J. Angew. Chem. Int. Ed. 2012; 51: 6828
- 2a Srinivasan R. J. Am. Chem. Soc. 1963; 85: 3048
- 2b Salomon RG, Kochi JK. J. Am. Chem. Soc. 1974; 96: 1137
- 2c Kochi JK. Angew. Chem. Int. Ed. 1988; 27: 1227
- 3 Nicewicz DA, MacMillan DW. C. Science 2008; 322: 77
- 4 Ischay MA, Anzovino ME, Du J, Yoon TP. J. Am. Chem. Soc. 2008; 130: 12886
- 5a Zou Y.-Q, Chen J.-R, Liu X.-P, Lu L.-Q, Davis RL, Jørgensen KA, Xiao W.-J. Angew. Chem. Int. Ed. 2012; 51: 784
- 5b Neumann M, Füldner S, König B, Zeitler K. Angew. Chem. Int. Ed. 2011; 50: 951
- 5c Hari DP, König B. Org. Lett. 2011; 13: 3852
- 5d Fidaly K, Ceballos C, Falguières A, Veitia MS.-I, Guy AFerroud C. Green. Chem. 2012; 14: 1293
- 6a Zen JM, Liou SL, Kumar AS, Hsia MS. Angew. Chem. Int. Ed. 2003; 42: 577
- 6b Cheng Y, Yang J, Qu Y, Li P. Org. Lett. 2012; 14: 98
- 7 Crank G, Mursyidi A. J. Photochem. Photobiol., A 1990; 53: 301
- 8a Rai A, Yadav LD. S. Tetrahedron Lett. 2010; 51: 4045
- 8b Patel R, Srivastava VP, Yadav LD. S. Synlett 2010; 1797
- 8c Rai A, Yadav LD. S. Tetrahedron Lett. 2011; 52: 3933
- 8d Rai A, Rai VK, Singh AK, Yadav LD. S. Eur. J. Org. Chem. 2011; 4302
- 8e Singh AK, Chawla RR, Rai A, Yadav LD. S. Chem. Commun. 2012; 48: 3766
- 8f Rai A, Yadav LD. S. Tetrahedron 2012; 68: 2459
- 9a Lazarides T, McCormick T, Du P, Luo G, Lindley B, Eisenberg R. J. Am. Chem. Soc. 2009; 131: 9192
- 9b Encinas MV, Rufs AM, Bertolotti SG, Previtali CM. Polymer 2009; 50: 2762
- 9c Lee SH, Nam DH, Park CB. Adv. Synth. Catal. 2009; 351: 2589
- 10 Iizawa Y, Okonogi K, Hayashi R, Iwahi T, Yamazaki T, Imada A. Antimicrob. Agents Chemother. 1993; 37: 100
- 11a Kohara Y, Kubo K, Imamiya E, Wada T, Inada Y, Naka T. J. Med. Chem. 1996; 39: 5228
- 11b Shen L, Zhang Y, Wang A, Sieber-McMaster E, Chen X, Pelton P, Xu JZ, Yang M, Zhu P, Zhou L, Reuman M, Hu Z, Russell R, Gibbs AC, Ross H, Demarest K, Murray WV, Kuo G.-H. J. Med. Chem. 2007; 50: 3954
- 11c Song YT, Connor DT, Sercel AD, Sorenson RJ, Doubleday R, Unangst PC, Roth BD, Beylin VG, Gilbertsen RB, Dyer RD. J. Med. Chem. 1999; 42: 1161
- 11d Ishikawa T, Iizawa Y, Okonogi K, Miyake A. J. Antibiot. 2000; 53: 1053
- 11e Marcinkeviciene J, Rogers MJ, Kopcho L, Jiang W, Wang K, Murphy DJ, Lippy J, Link S, Chung TD. Y, Hobbs F, Haque T, Trainor GL, Slee A, Stern AM, Copeland RA. Biochem. Pharmacol. 2000; 60: 339
- 11f Martinez A, Fernandez E, Castro A, Conde S, Rodriguez-Franco I, Bańos JE, Badia AE. J. Med. Chem. 2000; 35: 913
- 11g Lanzafame A, Christopoulos A. J. Pharmacol. Exp. Ther. 2004; 308: 830
- 12 Martinez A, Alonso M, Castro A, Pěrez C, Moreno FJ. J. Med. Chem. 2002; 45: 1292
- 13 Castro A, Castaño T, Encinas A, Porcal W, Gil C. Bioorg. Med. Chem. 2006; 14: 1644
- 14a Shah AA, Khan ZA, Choudhary N, Lohölter C, Schäfer S, Marie GP. L, Farooq U, Witulski B, Wirth T. Org. Lett. 2009; 11: 3578
- 14b Cheng D, Chen Z. Synth. Commun. 2002; 32: 2155
- 14c Yan M, Chen Z, Zheng Q. J. Chem. Res., Synop. 2003; 618
- 14d Patil PC, Bhalerao DS, Dangate PS, Akamanchi KG. Tetrahedron Lett. 2009; 50: 5820
- 15 Forlani L, Lugli A, Boga C, Corradi AB, Sgarabotto P. J. Heterocycl. Chem. 2000; 37: 63
- 16 Isobe T, Ishikawa T. J. Org. Chem. 1999; 64: 6989
- 17 Patil PC, Bhalerao DS, Dangate PS, Akamanchi KG. Tetrahedron Lett. 2009; 50: 5820
- 18 Fukumoto T, Matsuki T, Hu NX, Aso Y, Otsubo T, Ogura F. Chem. Lett. 1990; 2269
- 19 Hu NX, Aso Y, Otsubo T, Ogura F. Bull. Chem. Soc. Jpn. 1986; 59: 879
- 20a Mayhoub AS, Kiselev E, Cushman M. Tetrahedron Lett. 2011; 52: 4941
- 20b Cheng D, Luo R, Zheng W, Yan J. Synth. Commun. 2012; 42: 2007
- 21a Shimidzu T, Iyoda T, Koide Y. J. Am. Chem. Soc. 1985; 107: 35
- 21b Neckers DC. Valdes-Aguilera O. M. Adv. Photochem. 1993; 18: 315
- 22 Chang SH, Yon GH, Kim YH. Chem. Lett. 1986; 1291
- 23 General Procedure for the Synthesis of 1,2,4-Thiadiazoles 2 To a solution of thioamide 1 (1.0 mmol) in DMF (3 mL) was added eosin Y (2 mol%), and the mixture was irradiated with a household 18 W CFL (Philips, 6500 K, 1010 lm, 85 mA) with stirring under an air atmosphere (but no air bubbling) at r.t. for 4–6 h. After completion of the reaction (monitored by TLC), H2O (3 mL) was added, and the mixture was extracted with EtOAc (3 × 5 mL). The combined organic phases were dried over MgSO4, filtered, and evaporated under reduced pressure. The resulting crude product was purified by silica gel column chromatography using a gradient mixture of hexane–EtOAc as eluent to afford an analytically pure sample of 2. All the products are known compounds and were characterized by the comparison of their melting points and spectroscopic data with those reported in the literature.20,24
- 24 El-Wassimy MT. M, Jørgensen KA, Lawesson S.-O. Tetrahedron 1983; 39: 1729
For leading reviews, see: