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

doi:10.6023/cjoc201907037

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (2): 447-453.DOI: 10.6023/cjoc201907037 Previous Articles Next Articles

醋酸碘苯促进的氧化反应在构建2-氨基-1,3,4-噻二唑分子中的应用

陆雨函, 韩颖芝, 孙亚栋, 阿布力米提·阿布都卡德尔, 王多志, 刘晨江

新疆大学化学与化工学院乌鲁木齐 830046

收稿日期:2019-07-26 修回日期:2019-09-16 发布日期:2019-10-12
通讯作者: 孙亚栋, 王多志 E-mail:syd19791016@163.com;xjwangdz@sina.com
基金资助:
国家自然科学基金（Nos.21662032，21562039）和新疆大学博士科研启动基金（No.BS150225）资助项目.

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

Lu Yuhan, Han Yingzhi, Sun Yadong, Abdukader Ablimit, Wang Duozhi, Liu Chenjiang

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

Received:2019-07-26 Revised:2019-09-16 Published:2019-10-12
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21662032, 21562039) and the Xinjiang University Doctoral Science Foundation (No. BS150225).

1. 200447S.pdf.pdf(887KB)

Abstract

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.

Key words: hypervalent iodine, oxidation, aromatic aldehydes, thiadiazole

Cite this article

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[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] Wang, H.; Zhang, D.; Sheng, H.; Bolm, C. J. Org. Chem. 2017, 82, 11854.
[3] Akira, Y.; Viktor V. Z. Chem. Rev. 2016, 116, 3328.
[4] Ito, M.; Ogawa, C.; Yamaoka, N.; Fujioka, H.; Dohi, T.; Kita, Y. Molecules. 2010, 15, 1918.
[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] (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). (张怀远, 唐蓉萍, 石星丽, 颉林, 伍家卫, 有机化学, 2019, 39, 1837.)
[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.
[8] Du, Y. F.; Liu, R. H.; Linn, G.; Zhao, K. Org. Lett. 2006, 8, 5919.
[9] Ochiai, M.; Takeuchi, Y.; Katayama, T.; Sueda, T.; Miyamoto, K. J. Am. Chem. Soc. 2005, 127, 12244.
[10] Duan, Y.-N.; Zhang, Z.; Zhang, C. Org. Lett. 2016, 18, 6176.
[11] Chen, J.; Qu, H.; Peng, J.; Chen, C. Chin. J. Org. Chem. 2015, 35, 937(in Chinese). (陈静, 曲红梅, 彭静, 陈超, 有机化学, 2015, 35, 937.)
[12] Fan, H.; Pan, P.; Zhang, Y.; Wang, W. Org. Lett. 2018, 20, 7929.
[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] Jadhav, V. B.; Kulkarni, M. V.; Rasal, V. P.; Biradar, S. S.; Vinay, M. D. Eur. J. Med. Chem. 2008, 43, 1721.
[15] (a) Khazi, I.; Mahajanshetti, C.; Gadad, A.; Tarnalli, A.; Sultan-pur, 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] (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] (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] Patel, H. M.; Noolvi, M. N.; Goyal, A.; Thippeswamy, B. S. Eur. J. Med. Chem. 2013, 65, 119.
[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). (孙召慧, 黄伟, 贡云芸, 蓝健, 刘幸海, 翁建全, 李永曙, 谭成侠, 有机化学, 2013, 33, 2612.)
[20] Yang, S.-J.; Lee, S.-H.; Kwak, H.-J.; Gong, Y.-D. 2013, 78, 438.
[21] Yang, S.-J.; Choe, J.-H.; Gong, Y.-D. ACS Comb. Sci. 2016, 18, 499.
[22] Dogan, H. N.; Duran, A.; Rollas, S.; Sener, G.; Uysal, M. K.; Gülen, D. Bioorg. Med. Chem. 2002, 10, 2893.
[23] Li, Y. J.; Liu, L, J.; Jin, K. Xu, Y. T.; Sun, S. Q. Chin. Chem. Lett. 2010, 21, 293.
[24] John, P.; Lau, J.; Jones, R. C. F. Tetrahedron Lett. 2003, 44, 7825.
[25] (a) Li, Q -H. Chin. J. Org. Chem. 2011, 31, 2131(in Chinese). (李清寒, 有机化学, 2011, 31, 2131.)
(b) Das, A.; Mukherjee, S. L. J. Am. Chem. Soc. 1953, 75, 1241.
[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] (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] Darehkordi, A.; Zarezadeh Abarqouei, B.; Rahmani, F. J. Heterocycl. Chem. 2017, 54, 1872.
[29] Niu, P.; Kang, J.; Tian, X.; Song, L.; Liu, H.; Wu, J.; Yu, W.; Chang, J. J. Org. Chem. 2015, 80, 1018.
[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.
[31] Mullick, P.; Khan, S. A.; Verma, S.; Alam, O. Bull. Korean Chem. Soc. 2011, 32, 1011.
[32] Guan, P.; Wang, L.; Hou, X.; Wan, Y.; Tang, W.; Fang, H. Bioorg. Med. Chem. 2014, 22, 5766.
[33] Alegaon, S. G.; Alagawadi, K. R. Med. Chem. Res. 2012, 21, 816.
[34] Guda, D. R.; Cho, H. M.; Lee, M. E. RSC Adv. 2013, 3, 6813.
[35] Han, Y. Z.; Sun, Y. D.; Abdukader, A.; Liu, B. F.; Wang, D. Z. Catal. Lett. 2018, 148, 3486.
[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.
[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.
[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.
[39] Aryanasab, F.; Halimehjani, A. Z.; Saidi, M. R. Tetrahedron Lett. 2010, 51, 790.

醋酸碘苯促进的氧化反应在构建2-氨基-1,3,4-噻二唑分子中的应用

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

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Changjun Liu, Huiling Hu, Chenghong Liu, Chaojie Zhu, Tiandi Tang. Pd Supported on Mesoporous ETS-10 Zeolite Catalyst with Superior Catalytic Performances in Synthesizing 1,2-Diones from the Oxidation of Internal Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2953-2960.
[2]	Xiaoyu Zhang, Xinyan Li, Bing Cui, Zhihui Shao, Mingqin Zhao. Design, Synthesis and Antioxidant Activity of Tetrahydro-β-carbolines [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2885-2894.
[3]	Yanhua Gao, Yinpan Zhang, Yan Zhang, Tao Song, Yong Yang. Visible-Light-Induced Aerobic Oxidation of Alcohols over Surface Oxygen Vacancies-Enriched Nb₂O₅ [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2572-2579.
[4]	Ke Jing, Panke Zhang, Senmiao Xu. Application of 1,4-Azaborines in Organic and Transition Metal Catalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1742-1750.
[5]	Qifan Wang, Yuanquan Zhang, Li Xing, Yuanxiang Zhou, Chenyu Gong, Bangcan He, Nian Zhang, Yongjun Wu, Wei Xue. Design, Synthesis and Biological Activity of Myricetin Derivatives Containing 1,2,4-Triazolo[3,4-b]-1,3,4-thiadiazole [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1525-1536.
[6]	Ning Liu, Xiaodan Cuan, Hui Li, Xiyan Duan. Progress in the Study of α-Functionalization of Enaminone [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 602-621.
[7]	Zhihua Chen, Yan Hu, Lili Ma, Ziyi Zhang, Chuanxiang Liu. Rational Design of ortho-Vinylhydropyridine-Assisted Amino-fluorophore as Hypochlorite Fluorescent Probe [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 718-724.
[8]	Yu Zhao, Yurong Duan, Shihui Shi, Yubin Bai, Liangzhu Huang, Xiaojun Yang, Yantu Zhang, Bin Feng, Jianbo Zhang, Qiuyu Zhang. Recent Advances of Hypervalent Iodine(III) Reagents upon Visible Light Irradiation [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4106-4140.
[9]	Huaiyuan Zhang, Nuo Xu, Rongping Tang, Xingli Shi. Recent Advances in Asymmetric Dearomatization Reactions Induced by Chiral Hypervalent Iodine Reagents [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3784-3805.
[10]	Bin Wei, Zilong Zhou, Jinghao Qin, Zeyu Yan, Jiacheng Guo, Shu Lei, Yexiang Xie, Xuanhui Ouyang, Renjie Song. Electrochemical Oxidative C(sp³)—H Sulfonylation of Xanthenes with Sodium Sulfinates [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 186-194.
[11]	Biao Han, Yaoyao Zhang, Shuhan Chen, Mengge Zhao, Nan Li, Weishuang Li, Lei Zhu. Preparation of Axially Grafted Temperature-Responsive Chiral Salen Mn^III and Application in Asymmetric Epoxidation of Olefins in Water [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 244-253.
[12]	Junping Du, Shanshan Feng, Jie Zhang, Yonghui Zhang, Shiwen Wang, Lifeng Han, Junli Chen. Tris(4-ethynylphenyl)amine-Based Conjugated Microporous Polymers and Its Photocatalytic Water Splitting Hydrogen Evolution [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2967-2974.
[13]	Weikang Xia, Chuang Liu, Sheng Ye, Lei Wang, Ruiyuan Liu. Synthesis of A Sulfonamide-Substituted Benzothiadiazole-Based Fluorescent Dye and Study of Its Application for Long-Term Cancer Cell Tracking [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2535-2541.
[14]	Tingshu Cao, Xiangyang Wei, Min Luo, Yifei Wang, Zijun Pan, Cheng Xu, Guodong Yin. PhI(OAc)₂-Promoted Dehydrogenation Oxidation for the Synthesis of 2-(Aryl/alkylthio)phenols and 10H-Phenothiazines [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2079-2088.
[15]	Yi Zhou, Zhuojun Li, Minghui Hu, Zhaohua Yan, Sen Lin. Oxidation of Sulfides with SO₂F₂/H₂O₂/Base [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1545-1550.