Citation: Zhang Xiaopeng, Dong Shuxiang, Ding Qianqian, Fan Xuesen, Zhang Guisheng. Selenium-catalyzed oxidative carbonylation of 1, 2, 3-thiadiazol-5-amine with amines to 1, 2, 3-thiadiazol-5- ylureas[J]. Chinese Chemical Letters, ;2019, 30(2): 375-378. doi: 10.1016/j.cclet.2018.07.017 shu

Selenium-catalyzed oxidative carbonylation of 1, 2, 3-thiadiazol-5-amine with amines to 1, 2, 3-thiadiazol-5- ylureas

Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China

zhangxiaopengv@sina.com

zgs@htu.cn

Received Date: 7 June 2018
Revised Date: 13 July 2018
Accepted Date: 24 July 2018
Available Online: 25 February 2018

Figures(2)

A facile one-pot, economical approach to 1, 2, 3-thiadiazol-5-ylureas was developed via seleniumcatalyzed oxidative carbonylation of 1, 2, 3-thiadiazol-5-amine with a series of amines in one-pot manner in the presence of CO and O₂. This approach is featured with cheap and easily available raw materials, cheap and reusable catalyst selenium, one-pot procedure, high atomic economy, simple operations and no emission of corrosive wastes.
- Selenium,
- Oxidative carbonylation,
- 1, 2, 3-Thiadiazol-5-amine,
- 1, 2, 3-Thiadiazol-5-ylureas,
- Phase-transfer catalysis
1. [1]
  A. Kumari, P. Baskaran, L. Plackova, et al., J. Plant Physiol. 223(2018) 65-71. doi: 10.1016/j.jplph.2018.01.005
2. [2]
  S.K. Dwivedi, A. Arora, V.P. Singh, et al., Photosynthetica 56(2018) 478-486. doi: 10.1007/s11099-017-0695-2
3. [3]
  C.S. Schmidt, L. Mrnka, T. Frantik, et al., Plant Physiol. Biochem.120(2017) 120-131. doi: 10.1016/j.plaphy.2017.09.016
4. [4]
  M.C. Mok, D.W.S. Mok, D.J. Armstrong, et al., Phytochemistry 21(1982) 1509-1511. doi: 10.1016/S0031-9422(82)85007-3
5. [5]
  Y.S. Yang, Y. Zhang, M.G. Dong, et al., J. Hazard. Mater. 335(2017) 92-99. doi: 10.1016/j.jhazmat.2017.04.013
6. [6]
  K. Grossmann, Plant Physiol. 95(1991) 234-237. doi: 10.1104/pp.95.1.234
7. [7]
  Z.W. Zhang, H.H. Yang, Z.H. Gao, et al., J. Agric. Food Chem. 65(2017) 11273-11279. doi: 10.1021/acs.jafc.7b03522
8. [8]
  A. Abad, C. Agullo, A.C. Cunat, et al., J. Agric. Food Chem. 52(2004) 4675-4683. doi: 10.1021/jf049921+
9. [9]
  M.S. Pasa, A.F. Brighenti, C.P.D. Silva, et al., An. Acad. Bras. Cienc. 89(2017) 3103-3110. doi: 10.1590/0001-3765201720170644
10. [10]
  R. Mirzajani, Z. Ramezani, F. Kardani, Microchem. J. 130(2017) 93-101.
11. [11]
  A.D. Pavlista, Acta Hortic. 619(2003) 145-152.
12. [12]
  G. Enkhtaivan, D.H. Kim, M. Pandurangan, J. Photochem. Photobiol. B Biol. 173(2017) 493-498. doi: 10.1016/j.jphotobiol.2017.06.032
13. [13]
  T.A. Kalinina, Y.S. Shakhmina, T.V. Glukhareva, et al., Chem. Heterocycl. Com+. 50(2014) 1039-1046. doi: 10.1007/s10593-014-1561-9
14. [14]
  J. Nisler, M. Zatloukal, L. Spichal, et al., Patent, WO 2016037595 A1, 2016.
15. [15]
  X.F. Wu, X.J. Fang, L.P. Wu, et al., Acc. Chem. Res. 47(2014) 1041-1053. doi: 10.1021/ar400222k
16. [16]
  Q. Liu, H. Zhang, A.W. Lei, Angew. Chem. Int. Ed. 50(2011) 10788-10799. doi: 10.1002/anie.v50.46
17. [17]
  A. Brennfuhrer, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 48(2009) 4114-4133. doi: 10.1002/anie.v48:23
18. [18]
  X.F. Wu, H. Neumann, M. Beller, ChemSusChem 6(2013) 229-241. doi: 10.1002/cssc.v6.2
19. [19]
  K. Shi, S.Y. Huang, Z.Y. Zhang, et al., Chin. Chem. Lett. 28(2017) 70-74. doi: 10.1016/j.cclet.2016.06.005
20. [20]
  H.T. Zhang, L.J. Gu, X.Z. Huang, et al., Chin. Chem. Lett. 27(2016) 256-260. doi: 10.1016/j.cclet.2015.10.012
21. [21]
  N. Sonoda, Pure Appl. Chem. 65(1993) 699-706. doi: 10.1351/pac199365040699
22. [22]
  T. Mizuno, T. Nakai, M. Mihara, Synthesis (2010) 4251-4255.
23. [23]
  X.P. Zhang, Z.J. Tang, X.L. Niu, et al., Tetrahedron Lett. 57(2016) 5266-5270. doi: 10.1016/j.tetlet.2016.10.046
24. [24]
  X.P. Zhang, H.Z. Jing, J. Mol. Catal. A Chem. 302(2009) 137-141. doi: 10.1016/j.molcata.2008.12.012
25. [25]
  X.P. Zhang, H.Z. Jing, W.Y. Peng, et al., Chin. J. Org. Chem. 37(2017) 411-417. doi: 10.6023/cjoc201609013
26. [26]
  X.P. Zhang, H.Z. Jing, S.W. Lu, Synlett (2005) 1535-1538.
27. [27]
  T. Mizuno, T. Nakai, M. Mihara, Heteroat. Chem. 21(2010) 541-545. doi: 10.1002/hc.v21:7
28. [28]
  H. Wang, J. Ying, M. Lai, et al., Adv. Synth. Catal. 360(2018) 1693-1703. doi: 10.1002/adsc.v360.8
29. [29]
  N. Sonoda, T. Yasuhara, K. Kondo, et al., J. Am. Chem. Soc. 93(1971) 6344. doi: 10.1021/ja00752a099
1. [1]
  Jiajie Gu , Jiaxiang Gu , Lei Yu . Selenium and Alzheimer's disease. Chinese Chemical Letters, 2025, 36(8): 110727-. doi: 10.1016/j.cclet.2024.110727
2. [2]
  Jiahui Li , Qiao Shi , Ying Xue , Mingde Zheng , Long Liu , Tuoyu Geng , Daoqing Gong , Minmeng Zhao . The effects of in ovo feeding of selenized glucose on liver selenium concentration and antioxidant capacity in neonatal broilers. Chinese Chemical Letters, 2024, 35(6): 109239-. doi: 10.1016/j.cclet.2023.109239
3. [3]
  Xingyu Chen , Sihui Zhuang , Weiyao Yan , Zhengli Zeng , Jianguo Feng , Hongen Cao , Lei Yu . Synthesis, antibacterial evaluation, and safety assessment of Se@PLA as a potent bactericide against Xanthomonas oryzae pv. oryzae. Chinese Chemical Letters, 2024, 35(10): 109635-. doi: 10.1016/j.cclet.2024.109635
4. [4]
  Xiaoxue Li , Hongwei Zhou , Rongrong Qian , Xu Zhang , Lei Yu . A concise synthesis of Se/Fe materials for catalytic oxidation reactions of anthracene and polyene. Chinese Chemical Letters, 2025, 36(3): 110036-. doi: 10.1016/j.cclet.2024.110036
5. [5]
  Zhen Zhang , Xue-ling Chen , Xiu-Mei Xie , Tian-Yu Gao , Jing Qin , Jun-Jie Li , Chao Feng , Da-Gang Yu . Iron-promoted carbonylation–rearrangement of α-aminoaryl-tethered alkylidenecyclopropanes with CO₂: Facile synthesis of quinolinofurans. Chinese Chemical Letters, 2025, 36(4): 110056-. doi: 10.1016/j.cclet.2024.110056
6. [6]
  Chenxi Shang , Boxuan Lu , Chongbei Wu , Shuqing Zhou , Luyan Shi , Tayirjan Taylor Isimjan , Xiulin Yang . Inducing electronic rearrangement through Co₃B-Mo₂B₅ catalysts: Efficient dual-function catalysis for NaBH₄ hydrolysis and 4-nitrophenol reduction. Chinese Chemical Letters, 2025, 36(9): 111152-. doi: 10.1016/j.cclet.2025.111152
7. [7]
  You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I₂-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799
8. [8]
  Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
9. [9]
  Ying Liu , Jia Ji , Yinling Hou , Lilan Guo , Xuan Lv . Selenium’s Journey. University Chemistry, 2025, 40(7): 218-224. doi: 10.12461/PKU.DXHX202409046
10. [10]
  Hui Li , Yanxing Qi , Jia Chen , Juanjuan Wang , Min Yang , Hongdeng Qiu . Synthesis of amine-pillar[5]arene porous adsorbent for adsorption of CO₂ and selectivity over N₂ and CH₄. Chinese Chemical Letters, 2024, 35(11): 109659-. doi: 10.1016/j.cclet.2024.109659
11. [11]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
12. [12]
  Kun Wang , Tianxue Gong , Yaohuang Huang , Boyang Han , Hanxiao Yang , Pavlo O. Dral , Weiwei Fang . Bornylimidazo[1,5–a]pyridin-3-ylidene allylic Pd catalyst with optimal electronic and steric properties for synthesis of 3,3′-disubstituted oxindoles. Chinese Chemical Letters, 2025, 36(7): 110539-. doi: 10.1016/j.cclet.2024.110539
13. [13]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
14. [14]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
15. [15]
  Yanfen PENG , Xinyue WANG , Tianbao LIU , Xiaoshuo WU , Yujing WEI . Syntheses and luminescence of four Cd(Ⅱ)/Zn(Ⅱ) complexes constructed by 1,3‐bis(4H‐1,2,4‐triazole)benzene. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1416-1426. doi: 10.11862/CJIC.20250018
16. [16]
  Feng-Fan Yang , Yin-Kang Ding , Lin-Kai Wu , Jiayue Tian , Shuai Dou , Wenjing Wang , Linfeng Liang . A 1,3,5-triazine μ₃-bridged neutral Cu(Ⅰ) framework with enhanced stability and CO₂ capture selectivity. Chinese Chemical Letters, 2025, 36(12): 110550-. doi: 10.1016/j.cclet.2024.110550
17. [17]
  Yaping Zhang , Wei Zhou , Mingchun Gao , Tianqi Liu , Bingxin Liu , Chang-Hua Ding , Bin Xu . Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles. Chinese Chemical Letters, 2024, 35(4): 108836-. doi: 10.1016/j.cclet.2023.108836
18. [18]
  Chuyu Huang , Zhishan Liu , Linping Zhao , Zuxiao Chen , Rongrong Zheng , Xiaona Rao , Yuxuan Wei , Xin Chen , Shiying Li . Metal-coordinated oxidative stress amplifier to suppress tumor growth combined with M2 macrophage elimination. Chinese Chemical Letters, 2024, 35(12): 109696-. doi: 10.1016/j.cclet.2024.109696
19. [19]
  Yaqi Deng , Jian Xue , Xiang Wu , Shunying Liu . Highly regioselective electrochemical oxidative 2,1-azolization of alkenes with azoles and nucleophiles. Chinese Chemical Letters, 2025, 36(9): 110822-. doi: 10.1016/j.cclet.2025.110822
20. [20]
  Ping Lu , Baoyin Du , Ke Liu , Ze Luo , Abiduweili Sikandaier , Lipeng Diao , Jin Sun , Luhua Jiang , Yukun Zhu . Heterostructured In2O3/In2S3 hollow fibers enable efficient visible-light driven photocatalytic hydrogen production and 5-hydroxymethylfurfural oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100361-100361. doi: 10.1016/j.cjsc.2024.100361

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(1239)
HTML views(42)

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