Synlett 2017; 28(11): 1373-1377
DOI: 10.1055/s-0036-1588747
letter
© Georg Thieme Verlag Stuttgart · New York

Iron(III)/TEMPO-Catalyzed Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles by Oxidative Cyclization under Mild Conditions

Guofu Zhang
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: [email protected]
,
Yidong Yu
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: [email protected]
,
Yiyong Zhao
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: [email protected]
,
Xiaoqiang Xie
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: [email protected]
,
Chengrong Ding*
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 14 January 2017

Accepted after revision: 19 February 2017

Publication Date:
27 March 2017 (online)


◊ These authors contributed equally to this work.

Abstract

A simple and efficient cationic Fe(III)/TEMPO-catalyzed oxidative cyclization of aroyl hydrazones has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole derivatives. The reaction offers a broad scope, good functional-group tolerance, and high yields under mild conditions in the presence of O2.

Supporting Information

 
  • References and Notes

    • 1a Yale HL, Losee K. J. Med. Chem. 1966; 9: 478-478
    • 1b Adelstein GW. J. Med. Chem. 1973; 16: 309-309
    • 1c Saunders J, Cassidy M, Freedman SB, Harley EA, Iversen LL, Kneen C, MacLeod AM, Merchant KJ, Snow RJ, Baker R. J. Med. Chem. 1990; 33: 1128-1128
    • 1d Orlek BS, Blaney FE, Brown F, Clark MS. G, Hadley MS, Hatcher J, Riley GJ, Rosenberg HE, Wadsworth HJ, Wyman P. J. Med. Chem. 1991; 34: 2726-2726
    • 1e Fray MJ, Cooper K, Parry MJ, Richardson K, Steele J. J. Med. Chem. 1995; 38: 3514-3514
    • 1f Omar FA, Mahfouz NM, Rahman MA. Eur. J. Med. Chem. 1996; 31: 819-819
    • 1g Rai LK. M, Linganna N. Farmaco 2000; 55: 389-389
    • 1h Zheng X, Li Z, Wang Y, Chen W, Huang Q, Liu C, Song G. J. Fluorine Chem. 2003; 123: 163-163
    • 1i Almasirad A, Tabatabai SA, Faizi M, Kebriaeezadeh A, Mehrabi N, Dalvandi A, Shafiee A. Bioorg. Med. Chem. Lett. 2004; 14: 6057-6057
    • 1j Leung D, Du W, Hardouin C, Cheng H, Hwang I, Cravatt BF, Boger DL. Bioorg. Med. Chem. Lett. 2005; 15: 1423-1423
    • 1k Manojkumar P, Kochupappy T. Acta Pharm. (Zagreb, Croatia) 2009; 59: 159-159
    • 1l Srinivas K, Kumar KP. Int. J. Biopharm. 2010; 1: 14-14
    • 2a Adachi C, Baldo MA, Forrest SR, Thompson ME. Appl. Phys. Lett. 2000; 77: 904-904
    • 2b Mitschke U, Bäuerle P. J. Mater. Chem. 2000; 10: 1471-1471
    • 2c Lee Y.-Z, Chen X, Chen S.-A, Wei P.-K, Fann W.-S. J. Am. Chem. Soc. 2001; 123: 2296-2296
    • 2d Wang J, Wang R, Yang J, Zheng Z, Carducci MD, Cayou T, Peyghambarian N, Jabbour GE. J. Am. Chem. Soc. 2001; 123: 6179-6179
    • 2e Chan L.-H, Lee R.-H, Hsieh C.-F, Yeh H.-C, Chen C.-T. J. Am. Chem. Soc. 2002; 124: 6469-6469
    • 2f Guan M, Bian ZQ, Zhou YF, Li FY, Li ZJ, Huang CH. Chem. Commun. 2003; 2708-2708
    • 2g Yang X, Müller DC, Nether D, Meerholz K. Adv. Mater. (Weinheim, Ger.) 2006; 18: 948-948
    • 2h He GS, Tan L.-S, Zheng Q, Prasad PN. Chem. Rev. 2008; 108: 1245-1245
    • 3a Saikahi H, Shimojo N, Uehara Y. Chem. Pharm. Bull. 1972; 20: 1663-1663
    • 3b Werber G, Bucherri F, Noto R, Gentile M. J. Heterocycl. Chem. 1977; 14: 1385-1385
    • 3c Milcent R, Barbier G. J. Heterocycl. Chem. 1983; 20: 77-77
    • 3d Jedlovská E, Leško J. Synth. Commun. 1994; 24: 1879-1879
    • 3e Mruthyunjayaswamy BH. M, Shanthaveerappa BK. Indian J. Heterocycl. Chem. 1998; 8: 31-31
    • 3f Flidallah HM, Sharshira EM, Basaif SA, El-Kadar A-Ba-Oum A. Phosphorus, Sulfur Silicon Relat. Elem. 2002; 177: 67-67
    • 3g Rostamizadeh S, Ghasem Housaini SA. Tetrahedron Lett. 2004; 45: 8753-8753
    • 3h Dabiri M, Salehi P, Baghbanzadeh M. Tetrahedron Lett. 2006; 47: 6983-6983
    • 3i Majji G, Rout SK, Guin S, Gogoi A, Patel BK. RSC Adv. 2014; 4: 5357-5357
    • 4a Yang R, Dai L. J. Org. Chem. 1993; 58: 3381-3381
    • 4b Dobrotă C, Paraschivescu CC, Dumitru I, Matache M, Baciu I, Ruţă LL. Tetrahedron Lett. 2009; 50: 1886-1886
    • 4c Rao VS, Chandra Sekhar KV. G. Synth. Commun. 2004; 34: 2153-2153
    • 4d Shang Z. Synth. Commun. 2006; 36: 2927-2927
    • 4e Shang Z, Reiner J, Chang J, Zhao K. Tetrahedron Lett. 2005; 46: 2701-2701
    • 5a Guin S, Tuhin G, Rout SK, Banerjee A, Patel BK. Org. Lett. 2011; 13: 5976-5976
    • 5b Jiang H, Li X, Pan X, Zhou P. Pure Appl. Chem. 2011; 84: 553-553
    • 5c Yadav AK, Yadav LD. S. Tetrahedron Lett. 2014; 55: 2065-2065
  • 6 Kawano T, Yoshizumi T, Hirano K, Satoh T, Miura M. Org. Lett. 2009; 11: 3072-3072
  • 7 Zarudnitskii EV, Pervak II, Merkulov AS, Yurochenko AA, Tolmachev AA. Tetrahedron 2008; 64: 10431-10431
    • 8a Klingsberg E. J. Am. Chem. Soc. 1958; 80: 5786-5786
    • 8b Kerr VN, Ott DG, Hayes FN. J. Am. Chem. Soc. 1960; 82: 186-186
    • 8c Short FW, Long LM. J. Heterocycl. Chem. 1969; 6: 707-707
    • 8d Reddy CK, Reddy PS. N, Ratnam CV. Synthesis 1983; 842-842
    • 8e Al-Talib M, Tashtoush H, Odeh N. Synth. Commun. 1990; 20: 1811-1811
    • 9a Bentiss F, Lagrenée M, Barbry D. Synth. Commun. 2001; 31: 935-935
    • 9b Tandon VK, Chhor RB. Synth. Commun. 2001; 31: 1727-1727
    • 9c Mashraqui SH, Ghadigaonkar SG, Kenny RS. Synth. Commun. 2003; 33: 2541-2541
    • 9d Kangani CO, Kelley DE, Day BW. Tetrahedron Lett. 2006; 47: 6497-6497
  • 10 Zhang G, Wen X, Wang Y, Han X, Luan Z, Ding C, Cao X. RSC Adv. 2013; 3: 22918-22918
    • 11a Dong Y, Zhao X, Liu R. Chin. J. Chem. 2015; 33: 1019-1019
    • 11b Yin Y, Chu C, Lu Q, Tao J, Liang X, Liu R. Adv. Synth. Catal. 2010; 352: 113-113
    • 11c Zhang G, Liu R, Xu Q, Ma L, Liang X. Adv. Synth. Catal. 2006; 348: 862-862
  • 12 2-tert-Butyl-5-phenyl-1,3,4-oxadiazole (2a); Typical Procedure A mixture N′-(2,2-dimethylpropylidene)benzohydrazide (1a; 0.1021 g, 0.5 mmol), Fe(NO3)3·9H2O (0.0202 g, 0.05 mmol), MgSO4 (0.1204 g, 1.0 mmol), TEMPO (0.0078 g, 0.05 mmol), and DCE (5.0 mL) was added to a 100 mL sealed tube and vigorously stirred under O2 at 35 °C for 6 h. H2O (20.0 mL) was then added to the tube and the product was extracted with CH2Cl2 (3 × 15 mL). The organic phases were combined, dried (Na2SO4), and concentrated under a vacuum. The residue was purified by column chromatography to give a light yellow liquid; yield: 0.0931 g (92%). 1H NMR (500 MHz, DMSO-d 6): δ = 7.99 (dd, J = 8.0, 1.6 Hz, 2 H), 7.63–7.54 (m, 3 H), 1.42 (s, 9 H). 13C NMR (125 MHz, DMSO-d 6): δ = 172.67, 163.77, 131.71, 129.29, 126.37, 123.58, 32.02, 27.77. HRMS: m/z [M + 1]+ calcd for C12H15N2O: 203.1179; found: 203.1178.
  • 13 2,5-Diphenyl-1,3,4-oxadiazole (4a): Typical Procedure A mixture of N′-(benzylidene)benzohydrazide (0.1120 g, 0.5 mmol), Fe(NO3)3·9H2O (0.0202 g, 0.05 mmol), MgSO4 (0.1204 g, 1.0 mmol), TEMPO (0.0078 g, 0.05 mmol), and CH2Cl2 (5.0 mL) was added to a 100 mL sealed tube and vigorously stirred under O2 at 35 °C for 6 h. H2O (20.0 mL) was then added to the tube and the product was extracted with CH2Cl2 (3 × 15 mL). The organic phases were combined, dried (Na2SO4), and concentrated under a vacuum. The residue was purified by column chromatography to give a light yellow solid; yield: 0.0911 g (82%). 1H NMR (500 MHz, DMSO-d 6): δ = 8.15–8.08 (m, 4 H), 7.66–7.60 (m, 6 H). 13C NMR (125 MHz, DMSO-d 6): δ = 163.99, 131.99, 129.37, 126.65, 123.33. HRMS: m/z [M + 1]+ calcd for C14H11N2O: 223.0871; found: 223.0867.