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
1. [1]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
2. [2]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
3. [3]
  Xiaoning TANG , Shu XIA , Jie LEI , Xingfu YANG , Qiuyang LUO , Junnan LIU , An XUE . Fluorine-doped MnO₂ with oxygen vacancy for stabilizing Zn-ion batteries. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1671-1678. doi: 10.11862/CJIC.20240149
4. [4]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-. doi: 10.3866/PKU.WHXB202406029
5. [5]
  Jiaxin Su , Jiaqi Zhang , Shuming Chai , Yankun Wang , Sibo Wang , Yuanxing Fang . Optimizing Poly(heptazine imide) Photoanodes Using Binary Molten Salt Synthesis for Water Oxidation Reaction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408012-. doi: 10.3866/PKU.WHXB202408012
6. [6]
  Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201
7. [7]
  Jie ZHAO , Huili ZHANG , Xiaoqing LU , Zhaojie WANG . Theoretical calculations of CO₂ capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213
8. [8]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
9. [9]
  Wei HE , Jing XI , Tianpei HE , Na CHEN , Quan YUAN . Application of solar-driven inorganic semiconductor-microbe hybrids in carbon dioxide fixation and biomanufacturing. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 35-44. doi: 10.11862/CJIC.20240364
10. [10]
  Shuhui Li , Rongxiuyuan Huang , Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028
11. [11]
  Zitong Chen , Zipei Su , Jiangfeng Qian . Aromatic Alkali Metal Reagents: Structures, Properties and Applications. University Chemistry, 2024, 39(8): 149-162. doi: 10.3866/PKU.DXHX202311054
12. [12]
  Lin Ding , Jinpeng Zhang , Junfeng Li , Daying Liu . Color Catcher: A Marvelous Encounter of Starch and Iodine. University Chemistry, 2024, 39(6): 334-341. doi: 10.3866/PKU.DXHX202311064
13. [13]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
14. [14]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
15. [15]
  Yunting Shang , Yue Dai , Jianxin Zhang , Nan Zhu , Yan Su . Something about RGO (Reduced Graphene Oxide). University Chemistry, 2024, 39(9): 273-278. doi: 10.3866/PKU.DXHX202306050
16. [16]
  Linbao Zhang , Weisi Guo , Shuwen Wang , Ran Song , Ming Li . Electrochemical Oxidation of Sulfides to Sulfoxides. University Chemistry, 2024, 39(11): 204-209. doi: 10.3866/PKU.DXHX202401009
17. [17]
  Chuanming GUO , Kaiyang ZHANG , Yun WU , Rui YAO , Qiang ZHAO , Jinping LI , Guang LIU . Performance of MnO₂-0.39IrO_x composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1135-1142. doi: 10.11862/CJIC.20230459
18. [18]
  Zhihuan XU , Qing KANG , Yuzhen LONG , Qian YUAN , Cidong LIU , Xin LI , Genghuai TANG , Yuqing LIAO . Effect of graphene oxide concentration on the electrochemical properties of reduced graphene oxide/ZnS. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1329-1336. doi: 10.11862/CJIC.20230447
19. [19]
  Caixia Lin , Ting Liu , Zhaojiang Shi , Hong Yan , Keyin Ye , Yaofeng Yuan . Innovative Experiment of Electrochemical Dearomative Spirocyclization of N-Acyl Sulfonamides. University Chemistry, 2025, 40(4): 359-366. doi: 10.12461/PKU.DXHX202406107
20. [20]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001

Get Citation

PDF

XML

Metrics

PDF Downloads(32)
Abstract views(3926)
HTML views(794)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142