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]
  Peiyu Zhang , Aixin Song , Jingcheng Hao , Jiwei Cui . 高频超声法制备聚多巴胺薄膜综合实验. University Chemistry, 2025, 40(6): 210-214. doi: 10.12461/PKU.DXHX202407081
3. [3]
  Qi Zhang , Ziyu Liu , Hongxia Tan , Jun Tong , Dazhen Xu . Research Progress on Direct Synthesis of β-Hydroxy Sulfones via Difunctionalization of Olefins. University Chemistry, 2025, 40(11): 199-209. doi: 10.12461/PKU.DXHX202412064
4. [4]
  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
5. [5]
  Jichao XU , Ming HU , Xichang CHEN , Chunhui WANG , Leichen WANG , Lingyi ZHOU , Xing HE , Xiamin CHENG , Su JING . Construction and hydrogen peroxide-activated chemodynamic activity of ferrocene?benzoselenadiazole conjugate. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1495-1504. doi: 10.11862/CJIC.20250144
6. [6]
  Xiaolong Li , Shiqi Zhong , Xiangfeng Wei , Zhiqiang Liu , Pan Zhan , Jiehua Liu . Carbon Dioxide: From the Past to the Future. University Chemistry, 2026, 41(2): 242-247. doi: 10.12461/PKU.DXHX202503013
7. [7]
  Yucai Zhang , Jun Jiang . Electrochemical Carbon Dioxide Reduction to Ethylene. University Chemistry, 2026, 41(2): 190-196. doi: 10.12461/PKU.DXHX202503006
8. [8]
  Ruifeng CHEN , Chao XU , Jianting JIANG , Tianshe YANG . Gold nanorod/zinc oxide/mesoporous silica nanoplatform: A triple-modal platform for synergistic anticancer therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2272-2282. doi: 10.11862/CJIC.20250117
9. [9]
  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
10. [10]
  Qiang Zhang , Yuanbiao Huang , Rong Cao . Imidazolium-Based Materials for CO₂ Electroreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306040-0. doi: 10.3866/PKU.WHXB202306040
11. [11]
  Yanhui Guo , Li Wei , Zhonglin Wen , Chaorong Qi , Huanfeng Jiang . Recent Progress on Conversion of Carbon Dioxide into Carbamates. Acta Physico-Chimica Sinica, 2024, 40(4): 2307004-0. doi: 10.3866/PKU.WHXB202307004
12. [12]
  Zhaoyu Wen , Na Han , Yanguang Li . Recent Progress towards the Production of H₂O₂ by Electrochemical Two-Electron Oxygen Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(2): 2304001-0. doi: 10.3866/PKU.WHXB202304001
13. [13]
  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): 2406029-0. doi: 10.3866/PKU.WHXB202406029
14. [14]
  Hailang JIA , Pengcheng JI , Hongcheng LI . Preparation and performance of nickel doped ruthenium dioxide electrocatalyst for oxygen evolution. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1632-1640. doi: 10.11862/CJIC.20240398
15. [15]
  Hailian Cheng , Shuaiqiang Jia , Chunjun Chen , Haihong Wu , Buxing Han . Electrocatalytic CO₂ Conversion: A Key to Unlocking a Low-Carbon Future. University Chemistry, 2026, 41(2): 1-13. doi: 10.12461/PKU.DXHX202502023
16. [16]
  Jiayi Yang , Jianxiu Hao , Huacong Zhou , Quansheng Liu . “Gorgeous Transformation” of Carbon Dioxide into Cyclic Carbonates: Catalyst Types and Roles. University Chemistry, 2026, 41(2): 178-189. doi: 10.12461/PKU.DXHX202502105
17. [17]
  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
18. [18]
  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
19. [19]
  Jianan Hong , Chenyu Xu , Yan Liu , Changqi Li , Menglin Wang , Yanwei Zhang . Decoding the interfacial competition between hydrogen evolution and CO₂ reduction via edge-active-site modulation in photothermal catalysis. Acta Physico-Chimica Sinica, 2025, 41(9): 100099-0. doi: 10.1016/j.actphy.2025.100099
20. [20]
  Bizhu Shao , Huijun Dong , Yunnan Gong , Jianhua Mei , Fengshi Cai , Jinbiao Liu , Dichang Zhong , Tongbu Lu . Metal-Organic Framework-Derived Nickel Nanoparticles for Efficient CO₂ Electroreduction in Wide Potential Windows. Acta Physico-Chimica Sinica, 2024, 40(4): 2305026-0. doi: 10.3866/PKU.WHXB202305026

Get Citation

PDF

XML

Metrics

PDF Downloads(34)
Abstract views(5336)
HTML views(969)

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