Synthesis of 1,3,4-Oxadiazoles by Iodine-Mediated Oxidative Cyclization of Methyl Ketones with 4-Phenylsemicarbazide

Shanshan Zhang; Chuang Liu; Xiaojun Wu; Wen Li; He Li; Shiwei Wang; Yuting Leng; Yangjie Wu

doi:10.1055/a-1707-0965

Synlett, Inhaltsverzeichnis

Synlett 2022; 33(03): 269-272
DOI: 10.1055/a-1707-0965

letter

Synthesis of 1,3,4-Oxadiazoles by Iodine-Mediated Oxidative Cyclization of Methyl Ketones with 4-Phenylsemicarbazide

Shanshan Zhang

^aGreen Catalysis Center, and College of Chemistry, Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou 450001, P. R. of China

,

Chuang Liu

^aGreen Catalysis Center, and College of Chemistry, Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou 450001, P. R. of China

,

Xiaojun Wu

^aGreen Catalysis Center, and College of Chemistry, Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou 450001, P. R. of China

,

Wen Li

^aGreen Catalysis Center, and College of Chemistry, Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou 450001, P. R. of China

,

He Li

^aGreen Catalysis Center, and College of Chemistry, Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou 450001, P. R. of China

,

Shiwei Wang

^bSchool of Mechanics and Engineering Science, Zhengzhou University, Zhengzhou, Henan 450001, P. R. of China

,

Yuting Leng ∗

^aGreen Catalysis Center, and College of Chemistry, Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou 450001, P. R. of China

,

Yangjie Wu ∗

^aGreen Catalysis Center, and College of Chemistry, Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou 450001, P. R. of China

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

An efficient one-pot method has been developed to access 5-amino-2-(het)aroyl-1,3,4-oxadiazoles through I₂/DMSO-promoted oxidative cyclization of 4-phenylsemicarbazide with (het)aryl methyl ketones under mild conditions. This reaction proceeds smoothly with a wide range of methyl ketones containing various functional groups to give the corresponding products in moderate yields under mild conditions.

Keywords

one-pot reaction - oxadiazoles - oxidative cyclization - phenylsemicarbazide - methyl ketones

Volltext

Referenzen

References and Notes

1a Shi W, Qian X, Zhang R, Song G. J. Agric. Food Chem. 2001; 49: 124
1b Zou X.-J, Lai L.-H, Jin G.-Y, Zhang Z.-X. J. Agric. Food Chem. 2002; 50: 3757

2 Böstrom J, Hogner A, Llinàs A, Wellner E, Plowright AT. J. Med. Chem. 2012; 55: 1817
3 Lee J, Shizu K, Tanaka H, Nomura H, Yasuda T, Adachi C. J. Mater. Chem. C 2013; 1: 4599

4a Tan TM, Chen Y, Kong KH, Bai J, Li Y, Lim SG, Ang TH, Lam Y. Antiviral Res. 2006; 71: 7
4b Bajaj S, Asati V, Singh J, Roy PP. Eur. J. Med. Chem. 2015; 97: 124

5a Chidirala S, Ulla H, Valaboju A, Kiran MR, Mohanty ME, Satyanarayan MN, Umesh G, Bhanuprakash K, Rao VJ. J. Org. Chem. 2016; 81: 603
5b Belavagi NS, Deshapande N, Pujar GH, Wari MN, Inamdar SR, Khazi IA. M. J. Fluoresc. 2015; 25: 1323
5c Han J. J. Mater. Chem. C 2013; 1: 7779
5d Han J, Chui SS.-Y, Che C.-M. Chem. Asian J. 2006; 1: 814
5e Wen C.-R, Wang Y.-J, Wang H.-C, Sheu H.-S, Lee G.-H, Lai CK. Chem. Mater. 2005; 17: 1646

6 Ohmoto K, Yamamoto T, Okuma M, Horiuchi T, Imanishi H, Odagaki Y, Kawabata K, Sekioka T, Hirota Y, Matsuoka S, Nakai H, Toda M, Cheronis JC, Spruce LW, Gyorkos A, Wieczorek M. J. Med. Chem. 2001; 44: 1268
7 Otrubova K, Boger DL. ACS Chem. Neurosci. 2012; 3: 340
8 Yale HL, Losee K. J. Med. Chem. 1966; 9: 478

9a Kiselyov AS, Semenova MN, Chernyshova NB, Leitao A, Samet AV, Kislyi KA, Raihstat MM, Oprea T, Lemcke H, Lantow M, Weiss DG, Ikizalp NN, Kuznetsov SA, Semenov VV. Eur. J. Med. Chem. 2010; 45: 1683
9b Ouyang X, Piatnitski EL, Pattaropong V, Chen X, He H.-Y, Kiselyov AS, Velankar A, Kawakami J, Labelle M, Smith LII, Lohman J, Lee SP, Malikzay A, Fleming J, Gerlak J, Wang Y, Rosler RL, Zhou K, Mitelman S, Camara M, Surguladze D, Doody JF, Tuma MC. Bioorg. Med. Chem. Lett. 2006; 16: 1191

10a Yu W, Huang G, Zhang Y, Liu H, Dong L, Yu X, Li Y, Chang J. J. Org. Chem. 2013; 78: 10337
10b Gao Q, Liu S, Wu X, Zhang J, Wu A. Org. Lett. 2015; 17: 2960
10c Kumar D, Pilania M, Arun V, Mishra B. Synlett 2014; 25: 1137
10d Fan Y, He Y, Liu X, Hu T, Ma H, Yang X, Luo X, Huang G. J. Org. Chem. 2016; 81: 6820

11a Maghari S, Ramezanpour S, Darvish F, Balalaie S, Rominger F, Bijanzadeh HR. Tetrahedron 2013; 69: 2075
11b Prabhu G, Sureshbabu VV. Tetrahedron Lett. 2012; 53: 4232
11c Bao W, Chen C, Yi N, Jiang J, Zeng Z, Deng W, Peng Z, Xiang J. Chin. J. Chem. 2017; 35: 1611
11d Yang S.-J, Lee S.-H, Kwak H.-J, Gong Y.-D. J. Org. Chem. 2013; 78: 438
11e Kumar Sigalapalli D, Kadagathur M, Sujat Shaikh A, Jadhav GS, Bakchi B, Nagendra Babu B, Tangellamudi ND. ChemistrySelect 2020; 5: 13248

12a Andersen TL, Caneschi W, Ayoub A, Lindhardt AT, Couri MR. C, Skrydstrup T. Adv. Synth. Catal. 2014; 356: 3074
12b Ilangovan A, Saravanakumar S, Umesh S. J. Chem. Sci. (Berlin, Ger.) 2015; 127: 797
12c Brahmayya M, Liu F.-S, Suen S.-Y, Huang C.-C, Dai S.-A, Guo Y.-S, Chen Y.-F. Res. Chem. Intermed. 2015; 42: 1965

13 Kawano T, Yoshizumi T, Hirano K, Satoh T, Miura M. Org. Lett. 2009; 11: 3072
14 Fan X.-Y, Jiang X, Zhang Y, Chen Z.-B, Zhu Y.-M. Org. Biomol. Chem. 2015; 13: 10402
15 Guin S, Ghosh T, Rout SK, Banerjee A, Patel BK. Org. Lett. 2011; 13: 5976
16 Zhao Q, Ren L, Hou J, Yu W, Chang J. Org. Lett. 2019; 21: 210

17a Chu X, Wu Y, Lu H, Yang B, Ma C. Eur. J. Org. Chem. 2020; 2020: 1141
17b Li G.-H, Dong D.-Q, Yang Y, Yu X.-Y, Wang Z.-L. Adv. Synth. Catal. 2018; 361: 832
17c He Z.-Y, Guo J.-Y, Tian S.-K. Adv. Synth. Catal. 2018; 360: 1544
17d He Z.-Y, Huang C.-F, Tian S.-K. Org. Lett. 2017; 19: 4850

18a Fei Z, Zhu Y.-p, Liu M.-c, Jia F.-c, Wu A.-x. Tetrahedron Lett. 2013; 54: 1222
18b Jiang H, Huang H, Cao H, Qi C. Org. Lett. 2010; 12: 5561
18c Wu X, Zhao P, Geng X, Zhang J, Gong X, Wu Y.-d, Wu A.-x. Org. Lett. 2017; 19: 3319
18d Baig MF, Shaik SP, Nayak VL, Alarifi A, Kamal A. Bioorg. Med. Chem. Lett. 2017; 27: 4039
18e Yang L, Shi X, Hu B.-Q, Wang L.-X. Asian J. Org. Chem. 2016; 5: 494
18f Atmakur K, Kale A, Bingi C, Ragi N, Sripadi P, Tadikamalla P. Synthesis 2016; 49: 1603
18g Zhang Z, Xie C, Tan X, Song G, Wen L, Gao H, Ma C. Org. Chem. Front. 2015; 2: 942
18h Rajeshkumar V, Chandrasekar S, Sekar G. Org. Biomol. Chem. 2014; 12: 8512
18i Zhu Y.-P, Liu M.-C, Cai Q, Jia F.-C, Wu A.-X. Chem. Eur. J. 2013; 19: 10132

19 1,3,4-Oxadiazoles 3aa–ka; General Procedure A 25 mL Schlenk-flask equipped with a magnetic stirrer bar was charged with the appropriate methyl ketone 1 (0.2 mmol, 1.0 equiv.), I₂ (0.5 mmol), and DMSO (1.0 mL), and the mixture was heated at 110 °C for 1 h. 4-Phenylsemicarbazide (2; 0.24 mmol), K₂CO₃ (0.6 mmol), and DMSO (1.0 mL) were added, and the resulting mixture was stirred at 110 °C for 15 h. The reaction was then quenched with 5% aq Na₂S₂O₃ (20 mL), and the mixture was extracted with CH₂Cl₂ (3 × 20 mL). The organic layer was dried (Na₂SO₄) and concentrated, and the residue was purified by chromatography (silica gel). [5-(Phenylamino)-1,3,4-oxadiazol-2-yl](4-tolyl)methanone (3aa) Yellow solid; yield: 44.5 mg (80%); mp 201–203 °C. ¹H NMR (400 MHz, DMSO-d ₆): δ = 11.13 (s, 1 H), 8.23 (d, J = 8.4 Hz, 2 H), 7.58 (d, J = 8.0 Hz, 2 H), 7.37–7.32 (m, 4 H), 7.01 (t, J = 7.2 Hz, 1 H), 2.36 (s, 3 H). ¹³C NMR (100 MHz, DMSO-d ₆): δ = 176.6, 161.3, 156.6, 145.5, 138.3, 132.4, 130.8, 129.8, 129.7, 123.2, 118.0, 21.8. HRMS (ESI-TOF): m/z [M + H]⁺ calcd for C₁₆H₁₄N₃O₂: 280.1081; found: 280.1081. [5-(Phenylamino)-1,3,4-oxadiazol-2-yl](2-thienyl)methanone (3ca) Yellow solid; yield: 28.5 mg (53%); mp 199–202 °C. ¹H NMR (400 MHz, DMSO-d ₆): δ = 11.20 (s, 1 H), 8.54 (dd, J = 4.0, 1.2 Hz, 1 H), 8.24 (dd, J = 4.8, 1.2 Hz, 1 H), 7.66–7.63 (m, 2 H), 7.44–7.37 (m, 3 H), 7.09 (tt, J = 7.6, 1.2 Hz, 1 H). ¹³C NMR (100 MHz, DMSO-d ₆): δ = 169.0, 161.5, 156.0, 140.1, 138.3, 138.2, 137.1, 129.7, 129.6, 123.3, 118.1. HRMS (ESI-TOF) m/z [M + H]⁺ calcd for C₁₃H₁₀N₃O₂S: 272.0488; found: 272.0491. (3,4-Difluorophenyl)[5-(phenylamino)-1,3,4-oxadiazol-2-yl]methanone (3ka) Yellow solid; yield: 37.3 mg (62%); mp 199–202 °C. ¹H NMR (400 MHz, DMSO-d ₆): δ = 11.25 (s, 1 H), 8.39–8.34 (m, 1 H), 8.32–8.28 (m, 1 H), 7.76–7.69 (m, 1 H), 7.65–7.62 (m, 2 H), 7.43–7.39 (m, 2 H), 7.12–7.07 (m, 1 H). ¹³C NMR (100 MHz, DMSO-d ₆): δ = 174.5 (d, J _C–F = 1.4 Hz), 161.5, 156.4, 152.4 (d, J _C-F = 12.4 Hz), 148.4 (d, J _C-F = 13.0 Hz), 138.2, 132.3 (dd, J _C–F = 5.5, 3.3 Hz), 129.7, 128.7 (dd, J _C–F = 8.1, 3.3 Hz), 123.4, 119.8 (d, J _C–F = 18.8 Hz), 118.6 (d, J _C–F = 17.7 Hz), 118.1. ¹⁹F NMR (376 MHz, DMSO-d ₆): δ = –129.4 (d, J _F–F = 22.56 Hz), –137.1 (d, J _F–F = 22.18 Hz). HRMS (ESI-TOF): m/z [M + H]⁺ calcd for C₁₅H₁₀F₂N₃O₂: 302.0736; found: 302.0737.

Zusatzmaterial

Supporting Information