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]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  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
15. [15]
  Yan Kong , Wei Wei , Lekai Xu , Chen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO₂ Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049
16. [16]
  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): 2408012-0. doi: 10.3866/PKU.WHXB202408012
17. [17]
  Xiaofei Liu , He Wang , Li Tao , Weimin Ren , Xiaobing Lu , Wenzhen Zhang . Electrocarboxylation of Benzylic Phosphates and Phosphinates with Carbon Dioxide. Acta Physico-Chimica Sinica, 2024, 40(9): 2307008-0. doi: 10.3866/PKU.WHXB202307008
18. [18]
  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
19. [19]
  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
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(33)
Abstract views(4134)
HTML views(831)

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