Photocatalytic Oxidative Heterocyclization of Semicarbazones: An Efficient Approach for the Synthesis of 1,3,4-Oxadiazoles

Abstract

A highly efficient eosin Y catalyzed oxidative heterocyclization of semicarbazones was established under visible-light photoredox catalysis using CBr₄ as a bromine source. The protocol renders a rapid, mild, and efficient access to valuable 5-substituted 2-amino-1,3,4-oxadiazoles in an operationally simple way utilizing visible light and atmospheric oxygen.

Key words

visible light - eosin Y - photoredox catalysis - 1,3,4-oxadiazole - oxidative heterocyclization

• References and Notes


For selected reviews, see:
• 1a Zeitler K. Angew. Chem. Int. Ed. 2009; 48: 9785
• 1b Melchiorre P. Angew. Chem. Int. Ed. 2009; 48: 1360
• 1c Yoon TP, Ischay MA, Du J. Nat. Chem. 2010; 2: 527
• 1d Narayanam JM. R, Stephenson CR. J. Chem. Soc. Rev. 2011; 40: 102
• 1e Teply F. Collect. Czech. Chem. Commun. 2011; 76: 859
• 1f Tucke JW. R, Stephenson CR. J. J. Org. Chem. 2012; 77: 1617
• 2a Ciamician G. Science 1912; 36: 385
• 2b Sala X, Romero I, Rodriguze M, Lluis E, Llobet A. Angew. Chem. Int. Ed. 2009; 48: 2842
• 3a Kochi JK. Angew. Chem., Int. Ed. Engl. 1988; 27: 1227
• 3b Salomon RG, Kochi JK. J. Am. Chem. Soc. 1974; 96: 1137
• 3c Srinivasan R. J. Am. Chem. Soc. 1963; 85: 3048

For leading reviews on visible-light photoredox catalysis, see refs. 1a,c–e and:
• 4a Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
• 4b Xi Y, Yia H, Lei A. Org. Biomol. Chem. 2013; 11: 2387
• 4c Xuan J, Xiao W.-J. Angew. Chem. Int. Ed. 2012; 51: 6828
• 4d Juris AV, Barigelletti F, Campagna S, Belser P, von Zelewsky A. Coord. Chem. Rev. 1988; 84: 85
• 4e Kalyanasundaram K. Coord. Chem. Rev. 1982; 46: 159
• 5a Ravelli D, Fagnoni M, Albini A. Chem. Soc. Rev. 2013; 42: 97
• 5b Ravelli D, Fagnoni M. ChemCatChem 2012; 4: 169
• 5c Zou Y.-Q, Chen J.-R, Liu X.-P, Lu L.-Q, Davis RL. K, Jørgensen A, Xiao W.-J. Angew. Chem. Int. Ed. 2012; 51: 784
• 5d Fidaly K, Ceballos C, Falguières A, Veitia MS.-I, Guy A, Ferroud C. Green Chem. 2012; 14: 1293
• 5e Neumann M, Füldner S, König B, Zeitler K. Angew. Chem. Int. Ed. 2011; 50: 951
• 5f Hari DP, König B. Org. Lett. 2011; 13: 3852
• 5g Rey V, Soria-Castro SM, Argüello JE, Peñéñory AB. Tetrahedron Lett. 2009; 50: 4720
• 6 Zhang M, Chen C, Ma W, Zhao J. Angew. Chem. Int. Ed. 2008; 47: 9730

For selected reviews on oxidative reactions with molecular oxygen, see:
• 7a Roduner E, Kaim W, Sarkar B, Urlacher VB, Pleiss J, Gläser R, Einicke W.-D, Sprenger GA, Beifuß U, Klemm E, Liebner C, Hieronymus H, Hsu S.-F, Plietker B, Laschat S. ChemCatChem 2013; 5: 82
• 7b Wu W, Jiang H, Adimurthy S. Acc. Chem. Res. 2012; 45: 1736
• 7c Shi Z, Zhang C, Tang C, Jiao N. Chem. Soc. Rev. 2012; 41: 3381
• 7d Wendlandt AE, Suess AM, Stahl SS. Angew. Chem. Int. Ed. 2011; 50: 11062
• 7e Wendlandt AE, Suess AM, Stahl SS. Angew. Chem. Int. Ed. 2011; 50: 11062
• 7f Punniyamurthy T, Velusamy S, Iqbal J. Chem. Rev. 2005; 105: 2329
• 7g Stahl SS. Angew. Chem. Int. Ed. 2004; 43: 3400
• 8a Xuan J, Cheng Y, An J, Lu L.-Q, Zhang X.-X, Xiao W.-J. Chem. Commun. 2011; 47: 8337
• 8b Cheng Y, Yang J, Qu Y, Li P. Org. Lett. 2012; 14: 98
• 8c Condie A, G.-Gomez GJ. C, Stephenson CR. J. J. Am. Chem. Soc. 2010; 132: 1464
• 9 Holla BS, Gonaslaves R, Shenoy S. Eur. J. Med. Chem. 2000; 35: 267
• 10 Cesur N, Birteksoz S, Otuk G. Acta Pharm. Turcica 2002; 44: 23
• 11 Laddi UV, Desai S, Bennur RR. S, Bennur SC. Indian J. Heterocycl. Chem. 2002; 11: 319
• 12 Zou X, Zhang Z, Jin G. J. Chem. Res., Synop. 2002; 228
• 13 Zou XJ, Lai LH, Jin GY, Zhang ZX. J. Agric. Food Chem. 2002; 50: 3757
• 14 Palaska E, Sahin G, Kelicen P, Durlu NT, Altinok G. Farmaco 2002; 57: 101
• 15 Tyagi M, Kumar A. Oriental J. Chem. 2002; 18: 125
• 16 Holla BS, Poojary KN, Bhat KS, Ashok M, Poojary B. Indian J. Chem., Sect. B: Org Chem. Incl. Med. Chem. 2005; 44: 1669
• 17 Patli SG, Girisha M, Badiger J, Kudari SM, Purohit MG. Indian J. Heterocycl. Chem. 2007; 17: 37
• 18 Bhat MA, Siddiqui N, Khan SA. Polish. Pharm. Soc. 2008; 65: 235
• 19 Abdel HamidM. Acta. Chim. Slov. 2008; 55: 492
• 20 Almasirad A, Tabatabai SA, Faizi M. Biorg. Med. Chem. Lett. 2004; 14: 6057
• 21a de Oliveira CS, Lira BF, Barbosa-Filho JM, Lorenzo JG. F, de Athayde-Filho PF. Molecules 2012; 17: 10192
• 21b Shingalapur VR, Hosamani MK, Kallappa Keri RS. Eur. J. Med. Chem. 2010; 45: 1753
• 22 Boström J, Hogner A, Llinàs A, Wellner E, Plowright AT. J. Med. Chem. 2012; 55: 1817
• 23a James ND, Growcott JW. Drugs Future 2009; 34: 624
• 23b Scifinder Scholar. Criteria Used to Search: Research Topic: 1,3,4-Oxadiazole. Available online: http://www.cas.org/products/scifinder/ (accessed on 7 June 2012).
• 24 Wiedemann W. Chem. Z. 1982; 106: 313
• 25 Hill J. Comprehensive Heterocyclic Chemistry. Potts T. Pergamon Press; Oxford: 1984
• 26 Hetzheim A, Moeckel K. Adv. Heterocycl. Chem. 1966; 7: 183
• 27 Diana GD, Volkots DL, Nitz TJ, Biailly TR, Long MA, Vesico N, Aldous A, Pevear DC, Dukto FJ. J. Med. Chem. 1994; 37: 2421
• 28 Tandon VK, Chhor RB. Synth. Commun. 2001; 31: 1727
• 29 Carlsen HJ, Jorgensen KB. J. Heterocycl. Chem. 1994; 31: 805
• 30 Dost J, Heschel M, Stein J. Prakt J. Chem. 1985; 327: 109
• 31 Short FW, Long LM. J. Heterocycl. Chem. 1969; 6: 707
• 32a Al Talib M, Tashtoush Odeh HN. Synth. Commun. 1990; 20: 1811
• 32b Kerr NV, Ott DG, Hayes FN. J. Am. Chem. Soc. 1960; 82: 186
• 33 Butler RN, Scott O’Mahony FL T. A. F. Chem. Rev. 1973; 73: 93
• 34 Aboulwafa OM, Omar OM. M. E. Sulfur Lett. 1992; 14: 81
• 35 Omar FA, Mahfouz NM, Rahman MA. Eur. J. Med. Chem. 1996; 31: 819
• 36 Golovlyova SM, Moskvichev YA, Alov EM, Kobylinskey DB, Ermolaeva VV. Chem. Heterocycl. Compd. 2001; 37: 1102
• 37 Liu F, Wang B, Zhang Z. Youji Huaxue 2001; 21: 1126
• 38 Gani RS, Pujar SS, Gadaginamath GS. Indian J. Heterocycl. Chem. 2002; 12: 25
• 39 Wang X, Li Z, Wei B, Yang J. Synth. Commun. 2002; 32: 1097
• 40 Brain CT, Brunton SA. Synlett 2001; 382
• 41 Kidwai M, Bhatnagar D, Mishra NK. Green Chem. Lett. Rev. 2010; 3: 55
• 42 Srivastava VP, Yadav LD. S. Synlett 2013; 24: 2758
• 43a Patel R, Srivastava VP, Yadav LD. S. Synlett 2010; 1797
• 43b Rai A, Yadav LD. S. Tetrahedron Lett. 2011; 52: 3933
• 43c Rai A, Rai VK, Singh AK, Yadav LD. S. Eur. J. Org. Chem. 2011; 4302
• 43d Singh AK, Chawla R, Rai A, Yadav LD. S. Chem. Commun. 2012; 48: 3766
• 43e Rai A, Yadav LD. S. Tetrahedron 2012; 68: 2459
• 43f Srivastava VP, Yadav AK, Yadav LD. S. Synlett 2013; 24: 465
• 44 General Procedure for the Synthesis of 5-Aryl-1,3,4-Oxadiazoles 2 A solution of semicarbazone 1 (1 mmol), CBr₄ (1 mmol), and eosin Y (3, 1 mol%) in MeCN (3 mL) was irradiated with green LED at r.t. in an air atmosphere for 10–14 h. After completion of the reaction (indicated by TLC), it was quenched with sat. aq NaHCO₃ (5 mL) and extracted with EtOAc (3 × 5 mL). The combined organic phases were dried over anhydrous Na₂SO₄, filtered, and the solvent was removed under reduced pressure. The resulting crude product was purified by flash chromatography on silica gel [200–300 mesh; eluent: hexane–EtOAc (10:1 to 5:1)] to afford an analytically pure sample of 2-amino-5-aryl-1,3,4-oxadiazole 2. All the compounds are known and were characterized by comparison of their spectroscopic data with those reported in the literature (see ref. 45).
• 45a Kumar S. J. Chil. Chem. Soc. 2010; 55: 126
• 45b Sharma LK, Singh S, Singh RK. P. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2011; 50: 110
• 45c Lotfi B, Mustafa B, Leila B, Salima M. Int. J. Electrochem. Sci. 2011; 6: 1991
• 45d Blankenstein G, Moeckel K. Z. Chem. 1962; 69
• 45e Mano M, Seo T, Matsuno TK, Imai I. Chem. Pharm. Bull. 1976; 24: 2871
• 45f Bansal RK, Bhagchandani G. J. Indian Chem. Soc. 1982; 59: 277
• 45g Gehlen H, Möskel K. Justus Liebigs Ann. Chem. 1962; 651: 133
• 45h Grigat E, Puetter R. Chem. Ber. 1964; 97: 3560
• 45i Katritzky AR, Vvedensky V, Cai X, Rogovoy BV, Steel PJ. ARKIVOC 2002; (vi): 82
• 46a Nishina Y, Ohtani B, Kikushima K. Beilstein J. Org. Chem. 2013; 9: 1663
• 46b Poddubnyi IS, Belen KiiL. I, Krayushkin MM. Russ. Chem. Bull. 1996; 45: 1185
• 47a Neckers DC, Valdes-Aguilera OM. Adv. Photochem. 1993; 18: 315
• 47b Shimidzu T, Iyoda T, Koide Y. J. Am. Chem. Soc. 1985; 107: 35
• 48a Encinas MV, Rufs AM, Bertolotti SG, Previtali CM. Polymer 2009; 50: 2762
• 48b Lizarides T, McCormick T, Du P, Luo G, Lindley B, Eisenberg R. J. Am. Chem. Soc. 2009; 131: 9192
• 48c Lee SH, Nam DH. Park C. B. Adv. Synth. Catal. 2009; 351: 2589
• 49a Dhavale DD, Jachale SM. Molecules 2005; 10: 893
• 49b Du W, Zhao M.-N, Ren Z.-H, Wang Y.-Yu, Guan Z.-H. Chem. Commun. 2014; 50: 7437
• 49c Ichikawa J, Fujiwara M, Wada Y, Okauchi T, Minami T. Chem. Commun. 2000; 1887