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
Synlett 2022; 33(03): 269-272
DOI: 10.1055/a-1707-0965
DOI: 10.1055/a-1707-0965
letter
Synthesis of 1,3,4-Oxadiazoles by Iodine-Mediated Oxidative Cyclization of Methyl Ketones with 4-Phenylsemicarbazide
We gratefully acknowledge the financial support for this research provided by the National Science Foundation of China (51603192, 21172200) and the Natural Science Foundation of Henan Province (182300410211).
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 ketonesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1707-0965.
- Supporting Information
Publikationsverlauf
Eingereicht: 16. Oktober 2021
Angenommen nach Revision: 25. November 2021
Accepted Manuscript online:
25. November 2021
Artikel online veröffentlicht:
20. Dezember 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
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.