Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2016; 48(18): 3017-3030
DOI: 10.1055/s-0035-1561471
DOI: 10.1055/s-0035-1561471
feature
Synthesis of 3-Substituted 2,1-Benzisoxazoles by the Oxidative Cyclization of 2-Aminoacylbenzenes with Oxone
Further Information
Publication History
Received: 11 April 2016
Accepted after revision: 03 May 2016
Publication Date:
22 June 2016 (online)
Abstract
An efficient approach to the synthesis of 2,1-benzisoxazoles through direct construction of the N–O bond by the chemoselective oxidation of 2-aminoacylbenzenes with Oxone is described. This alternative methodology is characterized by its simple and transition-metal-free conditions and good functional group compatibility utilizing Oxone as a green oxidant instead of hypervalent iodine compounds. Moreover, this new procedure simplifies the number of steps compared to the previously reported procedure by circumventing the use of 2-azido-substituted aryl ketones.
Key words
Oxone - 2,1-benzisoxazoles - 2-aminoacylbenzenes - oxidative cyclization - transition-metal-freeSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561471.
- Supporting Information
-
References
- 1a Nimnual P, Tummatorn J, Thongsornkleeb C, Ruchirawat S. J. Org. Chem. 2015; 80: 8657
- 1b Zhang X, Huang R, Marrot J, Coeffard V, Xiong Y. Tetrahedron 2015; 71: 700
- 1c Whiting E, Lanning ME, Scheenstra JA, Fletcher S. J. Org. Chem. 2015; 80: 1229
- 1d Kalkhambar RG, Yuvaraj H. Synth. Commun. 2014; 44: 547
- 1e Dale TJ, Sather AC, Rebek JJr. Tetrahedron Lett. 2009; 50: 6173
- 1f Boulton AJ, Ghosh PB, Katritzky AR. Angew. Chem., Int. Ed. Engl. 1964; 3: 693
- 1g Smith PA. S, Brown BB, Putney RK, Reinisch PF. J. Am. Chem. Soc. 1953; 75: 6335
- 2a Deeks ED. Drugs 2010; 70: 1001
- 2b Benaka Prasad SB, Vinaya K, Ananda Kumar CS, Svarup S, Rangappa KS. Invest. New Drugs 2009; 27: 534
- 3a Chattopadhyaya Y, Upadhayaya RS. WIPO Patent Appl WO2009/091324, 2009
- 3b Angibaud PR. US Patent 20050148609 A1, 2005
- 3c Angibaud PR, Venet MG, Argoullon JM. WIPO Patent Appl WO03/087101 A1, 2003
- 3d Lyssicatos JP, Greca SD. L, Yang BV. US Patent 6495564, 2002
- 4a Pantyukhin AA, Pershina NN, Balandina SA, Aleksandrova GA, Makhumudov RR, Mikhailovskii AG. Pharm. Chem. J. 2013; 47: 195
- 4b Mani T, Wang F, Knabe WE, Sinn AL, Khanna M, Jo I, Sandusky GE, Sledge GW. Jr, Jones DR, Khanna R, Pollok KE, Meroueh SO. Bioorg. Med. Chem. 2013; 21: 2145
- 4c Wang F, Knabe WE, Li L, Jo I, Mani T, Roehm H, Oh K, Li J, Khanna M, Meroueh SO. Bioorg. Med. Chem. 2012; 20: 4760
- 4d Pierce AC, Jacobs M, Stuver-Moody C. J. Med. Chem. 2008; 51: 1972
- 4e Choquette D, Davies R, Green J, Ledeboer M, Moon Y.-C, Pierce A. US Patent 6825190, 2004
- 5a Orlov VY, Kotov AD, Tsivov AV, Rusakov AI. Russ. J. Org. Chem. 2015; 51: 245
- 5b Więclaw M, Bobin M, Kwast A, Bujok R, Wróbel Z, Wojciechowski K. Mol. Diversity 2015; 19: 807
- 5c Kotov AD, Prokaznikov MA, Antonova EA, Rusakov AI. Chem. Heterocycl. Compd. 2014; 50: 64 ; and references therein
- 6 Otley KD, Ellman JA. J. Org. Chem. 2014; 79: 8296
- 7a Chauhan J, Fletcher S. Tetrahedron Lett. 2012; 33: 4951
- 7b Kim BH, Jin Y, Jun YM, Han R, Baik W, Lee BM. Tetrahedron Lett. 2000; 41: 2337
- 7c Kim BH, Kim JM, Lee YS, Baik W, Lee BM. Heterocycles 1997; 45: 235
- 8a Golubev AS, Shidlovskii AF, Peregudov AS, Kagramanov ND. Russ. Chem. Bull., Int. Ed. 2014; 63: 2264
- 8b Stokes BJ, Vogel CV, Urnezis LK, Pan M, Driver TG. Org. Lett. 2010; 12: 2884
- 9 Prakash O, Saini RK, Singh SP, Varma RS. Tetrahedron Lett. 1997; 38: 3147
- 10 Swamy P, Reddy MM, Naresh M, Kumar MA, Srujana K, Durgaiah C, Narender N. Adv. Synth. Catal. 2015; 357: 1125
- 11a More AA, Ramana CV. Org. Lett. 2016; 18: 612
- 11b Kashiwa M, Kuwata Y, Sonoda M, Tanimori S. Tetrahedron 2016; 72: 304
- 11c Subba Reddy BV, Ravikumar Reddy C, Rajashekhar Reddy M. Org. Lett. 2015; 17: 3730
- 11d Zhang M.-Z, Ji P.-Y, Lin Y.-F, Guo C.-C. J. Org. Chem. 2015; 80: 10777
- 11e Swamy P, Reddy MM, Naresh M, Kumar MA, Srujana K, Durgaiah C, Narender N. Adv. Synth. Catal. 2015; 357: 1125
- 11f Padala AK, Saikam V, Ali A, Ahmed QN. Tetrahedron 2015; 71: 9388
- 11g Phatake RS, Ramana CV. Tetrahedron Lett. 2015; 56: 3868
- 11h Imai S, Kikui H, Moriyama K, Togo H. Tetrahedron Lett. 2015; 71: 5267
- 11i Venkateswarlu V, Balgotra S, Kumar KA. A, Vishwakarm RA, Sawant SD. Synlett 2015; 26: 1258
- 11j Venkateswarlu V, Kumar KA. A, Balgotra S, Reddy GL, Srinivas M, Vishwakarm RA, Sawant SD. Chem. Eur. J. 2014; 20: 6641
- 11k Adams AM, Du Bois J. Chem. Sci. 2014; 5: 656
- 11l Hlekhlai S, Samakkanad N, Sawangphon T, Pohmakotr M, Reutrakul V, Soorukram D, Jaipetch T, Kuhakarn C. Eur. J. Org. Chem. 2014; 7433
- 11m Lian X.-L, Lei H, Quan X.-J, Ren Z.-H, Wang Y.-Y, Guan Z.-H. Chem. Commun. 2013; 49: 8196
- 11n Yoshimura A, Zhu C, Middleton KR, Todora AD, Kastern BJ, Maskaev AV, Zhdankin VV. Chem. Commun. 2013; 49: 4800
- 12 Hussain WH, Green IR, Ahmed I. Chem. Rev. 2013; 113: 3329
- 13 Zhao XX, Zhang JC, Li SH, Yang QP, Li YC, Pang SP. Org. Process Res. Dev. 2004; 18: 886
- 14 Fields JD, Kropp PJ. J. Org. Chem. 2000; 65: 5937
- 15a Boduszek B, Halama A, Zon J. Tetrahedron 1997; 53: 11399
- 15b Elguero J In Comprehensive Heterocyclic Chemistry . Vol. 4. Katritzky AR, Rees CW. Pergamon Press; New York: 1984: 167
- 16 Arcadi A, Chiarini M, Del Vecchio L, Marinelli F, Michelet V. Chem. Commun. 2016; 52: 1458
- 17 Patil VV, Shankarling GS. J. Org. Chem. 2015; 80: 7876
- 18 Sakaue S, Tsubakino T, Nishiyama Y, Ishii Y. J. Org. Chem. 1993; 58: 3633
- 19a Khatri PK, Choudahary S, Singh R, Jain SL, Khatri OP. Dalton Trans. 2014; 43: 8054
- 19b Murray RW, Iyanar K, Chen J, Wearing JT. Tetrahedron Lett. 1996; 37: 808
- 20 Aslam AM, Rajagopal S, Vairamani M, Ravikumar M. Transition Met. Chem. 2011; 36: 751
- 21 Yang L, Shi G, Ke X, Shen R, Zhang L. CrystEngComm 2014; 16: 1620
- 22 Qadir MI, Scholten JD, Dupont J. Catal. Sci. Technol. 2015; 5: 1459
- 23 Patil VV, Gayakwad EM, Shankarling GS. J. Org. Chem. 2016; 81: 781
- 24a Zhao F, Zhao Q.-J, Zhao J.-X, Zhang D.-Z, Wu Q.-Y, Jin Y.-S. Chem. Nat. Compd. 2013; 49: 206
- 24b Donelly JA, Farrell DF. J. Org. Chem. 1990; 55: 1757
- 25 Arcadi A, Bernocchi E, Cacchi S, Marinelli F. Synlett 1991; 27
- 26a Cacchi S, Fabrizi G, Goggiamani A, Iazzetti A, Verdiglione R. Tetrahedron 2015; 71: 9346
- 26b Arcadi A, Blesi F, Cacchi S, Fabrizi G, Goggiamani A, Marinelli F. Tetrahedron 2013; 69: 1857
- 26c Bernini R, Cacchi S, Fabrizi G, Filisti E. Org. Lett. 2008; 10: 3457
- 27 Lou Z, Zhang S, Chen C, Pang X, Li M. Adv. Synth. Catal. 2014; 356: 153
- 28 Arcadi A, Bianchi G, Marinelli F. Synthesis 2004; 610
- 29 Pucheault M, Darses S, Genet J.-P. J. Am. Chem. Soc. 2004; 126: 15356
- 30 Parida KN, Moorthy JN. Tetrahedron 2014; 70: 2280
- 31 Phatake RS, Ramana CV. Tetrahedron Lett. 2015; 56: 2183
- 32 Jung ME, Deng G. Org. Lett. 2014; 16: 2142
- 33 Patil VV, Shankarling GS. J. Org. Chem. 2015; 80: 7876
- 34 Yakura T, Horiuchi Y, Nishimura Y, Yamada A, Nambu H, Fujiwara T. Adv. Synth. Catal. 2016; 358: 869
- 35 Climent MJ, Corma A, Iborra S, Martí L. ACS Catal. 2015; 5: 157
- 36 Jin GH, Ha SK, Park HM, Kang B, Kim SY, Kim H.-D, Ryu J.-H, Jeon R. Bioorg. Med. Chem. Lett. 2008; 18: 4092
- 37 Cheng S, Zhao L, Yu S. Adv. Synth. Catal. 2014; 356: 982
- 38 Patterson S, Alphey MS, Jones DC, Shanks EJ, Street IP, Frearson JA, Wyatt PG, Gilbert IH, Fairlamb AH. J. Med. Chem. 2011; 54: 6514
- 39 Lou Z, Zhang S, Chen C, Pang X, Li M, Wen L. Adv. Synth. Catal. 2014; 356: 153
- 40 Racys DT, Warrilow CE, Pimlott SL, Sutherland A. Org. Lett. 2015; 17: 4782
- 41 Bichovski P, Haas TM, Kratzert D, Streuff J. Chem. Eur. J. 2015; 21: 2339
- 42 Zhao D, Shen Q, Li J.-X. Adv. Synth. Catal. 2015; 357: 339
- 43 Stokes BJ, Vogel CV, Urnezis LK, Pan M, Driver TG. Org. Lett. 2010; 12: 2884
- 44 Robbins RJ, Laman DM, Falvey DE. J. Am. Chem. Soc. 1996; 118: 8127
- 45 Orlov VY, Kotov AD, Orlova TN, Ghanza VV. Chem. Heterocycl. Compd. 2005; 41: 630
- 46 Storz MP, Maurer CK, Zimmer C, Wagner N, Brengel C, de Jong JC, Lucas S, Müsken M, Häussler S, Steinbach A, Hartmann RW. J. Am. Chem. Soc. 2012; 134: 16143