Citation: Lu Yuhan, Han Yingzhi, Sun Yadong, Abdukader Ablimit, Wang Duozhi, Liu Chenjiang. Application of Iodobenzene Acetate Promoted Oxidation in the Synthesis of 2-Amino-1, 3, 4-thiadiazole Molecules[J]. Chinese Journal of Organic Chemistry, ;2020, 40(2): 447-453. doi: 10.6023/cjoc201907037 shu

Application of Iodobenzene Acetate Promoted Oxidation in the Synthesis of 2-Amino-1, 3, 4-thiadiazole Molecules

College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046

Corresponding author: Sun Yadong, syd19791016@163.com Wang Duozhi, xjwangdz@sina.com
Received Date: 26 July 2019
Revised Date: 16 September 2019
Available Online: 12 February 2019
Fund Project: Project supported by the National Natural Science Foundation of China 21562039Project supported by the National Natural Science Foundation of China (Nos. 21662032, 21562039) and the Xinjiang University Doctoral Science Foundation (No. BS150225)Project supported by the National Natural Science Foundation of China Nos. 21662032the Xinjiang University Doctoral Science Foundation No. BS150225

Figures(4)

A highly method for intramolecular oxidative coupling reaction of thiosemicarbazone promoted by hypervalent iodine reagent was reported. 2-Amino-1, 3, 4-thiadiazole derivatives could be synthesized effectively. Hypervalent iodine could be used as a mild reagent with low toxicity, low cost, easy circulation and operation. The reaction had the advantages of easy preparation of raw materials, simple operation and better performance. The applicability of substrates and the reaction mechanism were also preliminarily studied.
- hypervalent iodine,
- oxidation,
- aromatic aldehydes,
- thiadiazole
1. [1]
  (a) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523. (b) Stang. P. J. J. Org. Chem. 2003, 68, 2997. (c) Wirth, T. Top. Curr. Chem. 2003, 224, 185. (d) Tohma, H.; Kita, Y. Adv. Synth. Catal. 2004, 346, 111. (e) Moriarty, R. M. J. Org. Chem. 2005, 70, 2893. (f) Richardson, R. D.; Wirth, T. Angew. Chem., Int. Ed. 2006, 45, 4402. (g) Merritt, E. A.; Olofsson, B. Angew. Chem., Int. Ed. 2009, 48, 9052. (h) Brand, J. P.; González, D. F.; Nicolai, S.; Waser, J. Chem. Commun. 2011, 47, 102. (i) Collet, F.; Lescot, C.; Dauban, P. Chem. Soc. Rev. 2011, 40, 1926. (j) Louillat, M. L.; Patureau, F. W. Chem. Soc. Rev. 2014, 43, 901. (k) Kikugawa, Y.; Kawase, M. Chem. Lett. 1990, 4, 581. (l) Li, J.; Yang, S.; Wu, W.; Jiang, H. J. Org. Chem. 2018, 1284. (m) Wardrop, D. J.; Basak, A. Org. Lett. 2001, 3, 1053. (n) Wardrop, D. J.; Burge, M. S. Chem. Commun. 2004, 10, 1230.
2. [2]
  Wang H., Zhang D., Sheng H., Bolm C. J...Org. Chem., 2017, 82:11854. doi: 10.1021/acs.joc.7b01535
3. [3]
  Akira Y., Viktor V. Z. Chem. Rev., 2016, 116:3328. doi: 10.1021/acs.chemrev.5b00547
4. [4]
  Ito M., Ogawa C., Yamaoka N., Fujioka H., Dohi T., Kita Y...Molecules., 2010, 15:1918. doi: 10.3390/molecules15031918
5. [5]
  (a) Mao, L.; Li, Y.; Xiong, T.; Sun, K.; Zhang, Q. J. Org. Chem. 2013, 78, 733. (b) Chen, H.; Kaga, A.; Chiba. S. Org. Lett. 2014, 16, 6136. (c) Kiyokawa, K.; Kosaka, T.; Minakata, S. Org. Lett. 2014, 16, 4646.
6. [6]
  (a) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523. (b) Zhang, H. Y.; Tang, R. P.; Shi, X. L.; Xie, L.; Wu, J. W. Chin. J. Org. Chem. 2019, 39, 1837 (in Chinese).
7. [7]
  Yoshimura A., Middleton K. R., Todora A. D., Kastern B. J., Koski S. R., Maskaev A. V., Zhdankin V. V...Org. Lett., 2013, 15:4010. doi: 10.1021/ol401815n
8. [8]
  Du Y. F., Liu R. H., Linn G., Zhao K...Org. Lett., 2006, 8:5919. doi: 10.1021/ol062288o
9. [9]
  Ochiai M., Takeuchi Y., Katayama T., Sueda T., Miyamoto K. J...Am. Chem. Soc., 2005, 127:12244. doi: 10.1021/ja0542800
10. [10]
  Duan Y.-N., Zhang Z., Zhang C...Org. Lett., 2016, 18:6176. doi: 10.1021/acs.orglett.6b03209
11. [11]
  Chen J., Qu H., Peng J., Chen C...Chin. J. Org. Chem., 2015, 35:937(in Chinese).
12. [12]
  Fan H., Pan P., Zhang Y., Wang W...Org. Lett., 2018, 20:7929. doi: 10.1021/acs.orglett.8b03503
13. [13]
  (a) Lamani, R. S.; Shetty, N. S.; Kamble, R. R.; Khazi, I. A. M. Eur. J. Med. Chem. 2009, 44, 2828. (b) Alagawadi, K. R.; Alegaon, S. G. Arabian J. Chem. 2011, 4, 465. (c) Chandrakantha, B.; Isloor, A. M.; Shetty, P.; Fun, H. K.; Hegde, G. Eur. J. Med. Chem. 2014, 71, 316.
14. [14]
  Jadhav V. B., Kulkarni M. V., Rasal V. P., Biradar S. S., Vinay M. D...Eur. J. Med. Chem., 2008, 43:1721. doi: 10.1016/j.ejmech.2007.06.023
15. [15]
  (a) Khazi, I.; Mahajanshetti, C.; Gadad, A.; Tarnalli, A.; Sultanpur, C. Arzneim. Forsch. 1996, 46, 949. (b) Farghaly, A. R.; Esmail, S.; Abdel-Zaher, A.; Abdel-Hafez, A.; El-Kashef, H. Bioorg. Med. Chem. 2014, 22, 2166.
16. [16]
  (a) Gadad, A. K.; Noolvi, M. N.; Karpoormath, R. V. Bioorg. Med. Chem. 2004, 12, 5651. (b) Palkar, M. B.; Noolvi, M. N.; Maddi, V. S.; Ghatole, M.; Nargund, L. G. Med. Chem. Res. 2012, 21, 1313. (c) Joshi, S.; Manish, K.; Badiger, A. Med. Chem. Res. 2013, 22, 869.
17. [17]
  (a) Karki, S. S.; Panjamurthy, K.; Kumar, S.; Nambiar, M.; Ramareddy, S. A.; Chiruvella, K. K.; Raghavan, S. C.; Raghavan, S. C. Eur. J. Med. Chem. 2011, 46, 2109. (b) Noolvi, M. N.; Patel, H. M.; Singh, N.; Gadad, A. K.; Cameotra, S. S.; Badiger, A.Eur. J. Med. Chem. 2011, 46, 4411. (c) El-Gohary, N. S.; Shaaban, M. I. Eur. J. Med. Chem. 2013, 63, 185.
18. [18]
  Patel H. M., Noolvi M. N., Goyal A., Thippeswamy B. S...Eur. J. Med. Chem., 2013, 65:119. doi: 10.1016/j.ejmech.2013.04.020
19. [19]
  Sun Z., Huang W., Gong Y., Lan J., Liu X., Weng J., Li Y., Tan C...Chin. J. Org. Chem., 2013, 33:2612(in Chinese).
20. [20]
  Yang, S.-J.; Lee, S.-H.; Kwak, H.-J.; Gong, Y.-D. 2013, 78, 438.
21. [21]
  Yang S.-J., Choe J.-H., Gong Y.-D...ACS Comb. Sci., 2016, 18:499. doi: 10.1021/acscombsci.6b00071
22. [22]
  Dogan H. N., Duran A., Rollas S., Sener G., Uysal M. K., Gülen D...Bioorg. Med. Chem., 2002, 10:2893. doi: 10.1016/S0968-0896(02)00143-8
23. [23]
  Li Y. J., Liu, L J., Jin K...Xu Y. T., Sun S. Q...Chin. Chem. Lett., 2010, 21:293. doi: 10.1016/j.cclet.2009.11.008
24. [24]
  John P., Lau J., Jones R. C. F...Tetrahedron Lett., 2003, 44:7825. doi: 10.1016/j.tetlet.2003.08.077
25. [25]
  (a) Li, Q -H. Chin. J. Org. Chem. 2011, 31, 2131 (in Chinese).
26. [26]
  (a) Huang, J.; Liang, Y. J.; Pan, W.; Yang.; Dong, D. W. Org. Lett. 2007, 9, 5345. (b) Abdukader, A.; Sun, Y. D.; Zhang, Z. P.; Liu, C. J. Catal. Commun. 2018, 105, 43. (c) Yu, W. Q.; Du, Y. F.; Zhao, K. Org. Lett. 2009, 11, 2417. (d) Alla, S. K.; Kumar, R. K.; Sadhu, P.; Punniyamurthy, T. Org. Lett. 2013, 15, 1334. (e) Dohi, T.; Minamitsuji, Y.; Maruyama, A.; Hirose, S.; Kita, Y. Org. Lett. 2008, 10, 3559. (f) Koleda, O.; Broese, T.; Noetzel, J.; Roemelt, M.; Suna, E.; Francke, R. J. Org. Chem. 2017, 82, 1669. (g) Wang, Q. Q.; Xu, K.; Jiang, Y. Y.; Liu, Y. G.; Sun, B. G.; Zeng, C. C. Org. Lett. 2017, 19, 5517. (h) Suzuki, S.; Kamo, T.; Fukushi, K.; Hiramatsu, T.; Tokunaga, E.; Dohi, T.; Kita, Y.; Shibata, N. Chem. Sci. 2014, 5, 2754.
27. [27]
  (a) Yang, R.; Dai, L. J. Org. Chem. 1993, 58, 3381. (b) Gowramma, B; Avinash, K. A.; Gomathy, S.; Kandula, R. K. J. Pharm. Res. 2012, 5, 58.
28. [28]
  Darehkordi A., Zarezadeh Abarqouei B., Rahmani F. J...Heterocycl. Chem., 2017, 54:1872. doi: 10.1002/jhet.2779
29. [29]
  Niu P., Kang J., Tian X., Song L., Liu H., Wu J., Yu W., Chang J. J...Org. Chem., 2015, 80:1018. doi: 10.1021/jo502518c
30. [30]
  Zender M., Klein T., Henn C., Kirsch B., Maurer C. K., Kail D., Ritter C., Dolezal O., Steinbach A., Hartmann R. W. J...Med. Chem., 2013, 56:6761. doi: 10.1021/jm400830r
31. [31]
  Mullick P., Khan S. A., Verma S., Alam O...Bull. Korean Chem. Soc., 2011, 32:1011. doi: 10.5012/bkcs.2011.32.3.1011
32. [32]
  Guan P., Wang L., Hou X., Wan Y., Tang W., Fang H...Bioorg. Med. Chem., 2014, 22:5766. doi: 10.1016/j.bmc.2014.09.039
33. [33]
  Alegaon S. G., Alagawadi K. R...Med. Chem. Res., 2012, 21:816. doi: 10.1007/s00044-011-9598-0
34. [34]
  Guda D. R., Cho H. M., Lee M. E...RSC Adv., 2013, 3:6813. doi: 10.1039/c3ra00159h
35. [35]
  Han Y. Z., Sun Y. D., Abdukader A., Liu B. F., Wang D. Z...Catal. Lett., 2018, 148:3486. doi: 10.1007/s10562-018-2541-y
36. [36]
  Linciano P., Dawson A., Pöhner I., Costa D. M., Sá M. S., Cordeiro-da-Silva A., Luciani R., Gul S., Witt G., Ellinger B., Kuzikov M., Gribbon P., Reinshagen J., Wolf M., Behrens B., Hannaert V., Michels P. A. M., Nerini E., Pozzi C., di Pisa F., Landi G., Santarem N., Ferrari S., Saxena P., Lazzari S., Cannazza G., Freitas-Junior L. H., Moraes C. B., Pascoalino B. S., Alcântara L. M., Bertolacini C. P., Fontana V., Wittig U., Müller W., Wade R. C., Hunter W. N., Mangani S., Costantino L., Costi M. P...ACS Omega, 2017, 2:5666. doi: 10.1021/acsomega.7b00473
37. [37]
  Polkam N., Rayam P., Anireddy J. S., Yennam S., Anantaraju H. S., Dharmarajan S., Perumal Y., Kotapalli S. S., Ummanni R., Balasubramanian S...Bioorg. Med. Chem. Lett., 2015, 25:1398. doi: 10.1016/j.bmcl.2015.02.052
38. [38]
  Xue X. J., Wang Y. B., Lu P., Shang H. F., She J. X., Xia L. X., Qian H., Huang W. L...Chem. Pharm. Bull., 2014, 62:524. doi: 10.1248/cpb.c13-00964
39. [39]
  Aryanasab F., Halimehjani A. Z., Saidi M. R...Tetrahedron Lett., 2010, 51:790. doi: 10.1016/j.tetlet.2009.11.100
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