Citation: Liu Tianbao, Peng Yanfen, Gui Meifang, Zhang Min. Metal-Free Rapid Synthesis of 2-Aroylamino Naphtho[1, 2-d]thiazoles[J]. Chinese Journal of Organic Chemistry, ;2019, 39(11): 3199-3206. doi: 10.6023/cjoc201904029 shu

Metal-Free Rapid Synthesis of 2-Aroylamino Naphtho[1, 2-d]thiazoles

Key Laboratory of Micro-nano Powder and Advanced Energy Materials of Anhui Higher Education Institutes, Department of Chemical and Material Engineering, Chizhou University, Chizhou, Anhui 247000

Corresponding author: Liu Tianbao, tianbaoliu1979@126.com Zhang Min, 287323206@qq.com
Received Date: 11 April 2019
Revised Date: 27 May 2019
Available Online: 2 November 2019
Fund Project: the Natural Science Foundation of Anhui Province 1808085QB48the National Natural Science Foundation of China 21271035the Provincial Teaching Team of Organic Chemistry 2017jxtd051Project supported by the National Natural Science Foundation of China (No. 21271035), the Natural Science Foundation of Anhui Province (No. 1808085QB48) and the Provincial Teaching Team of Organic Chemistry (No. 2017jxtd051)

Figures(1)

A novel and efficient approach has been developed to synthesize 2-aroylamino naphtho[1, 2-d]thiazole compounds through the reaction between 3-[1-(4-substituted naphthyl)]-1-aroylthiourea and iodosobenzene diacetate (IBD) under ambient air. A library of naphtho[1, 2-d]thiazole derivatives having a variety of substituents has been synthesized. A plausible reaction pathway has been predicted. This reaction offers a metal-free synthesis, broad substrate scope, easily accessible reactants, excellent regioselectivity, room temperature reaction conditions under ambient air. The reported method is the efficient approach for the synthesis of naphtho[1, 2-d]thiazole derivatives.
- naphtho[1, 2-d]thiazole,
- thiourea,
- iodosobenzene diacetate,
- metal-free
1. [1]
  (a) Joy, H. B.; Bogert, M. T. J. Org. Chem. 1936, 1, 236.
  (b) Keyes, G. H.; Brooker, L. G. S. J. Am. Chem. Soc. 1937, 59, 74.
  (c) Akins, D. L.; özçelik, S.; Zhu, H.-R.; Guo, C. J. Phys. Chem. A 1997, 101, 3251.
  (d) Urano, T.; Hino, E. Imaging Sci. J. 1999, 47, 127.
  (e) Huang, W.; Zhang, X.-H.; Wang, L.-Y.; Zhai, G.-H.; Wen, Z.-Y.; Zhang, Z.-X. J. J. Mol. Struct. 2010, 977, 39.
2. [2]
  (a) Perrone, R.; Berardi, F.; Colabufo, N. A.; Tortorella, V.; Fornaretto, M. G.; Caccia, C.; Mcarthur, R. A. Eur. J. Med. Chem. 1997, 32, 739.
  (b) Li, Z.-G.; Yang, Q.; Qian, X.-H. Bioorg. Med. Chem. 2005, 13, 3149.
  (c) Hu, H.; Owwns, E. A.; Su, H.-R.; Yan, L.-L.; Lecitz, A.; Zhao, X.-Y.; Henary, M.; Zheng, Y. J. G. J. Med. Chem. 2015, 58, 1228.
3. [3]
  (a) El-Shishtawy, R. M.; Asiri, A. M.; Basaif, S. A.; Sobahi, T. R. Spectrochim. Acta A 2010, 75, 1605.
  (b) Aiken, S.; Allsopp, B.; Booth, K.; Gabbutt, C. D.; Heron, B. M.; Rice, C. R. Tetrahedron 2014, 70, 9352.
  (c) Yang, W.; Liu, C.-L.; Gao, Q.-Y.; Du, J.-Y.; Shen, P.; Liu, Y.; Yang, C.-Y. Opt. Mater. 2017, 66, 623.
  (d) Liu, C.-L.; Yang, W.; Gao, Q.-Y.; Du, J.-Y.; Luo, H.-J.; Liu, Y.; Yang, C.-Y. J. Lumin. 2018, 197, 193.
4. [4]
  (a) Lau, P. T. S.; Gompf, T. E. J. Org. Chem. 1970, 35, 4103.
  (b) Ulrich, P.; Cerami, A. J. Med. Chem. 1982, 25, 654.
  (c) El-Taweel, F. M. A. A.; Elnagdi, M. H. J. Heterocycl. Chem. 2001, 38, 981.
  (d) Al-Saleh, B.; El-Apasery, M. A.; Abdel-Aziz, R. S.; Elnagdi, M. H. J. Heterocycl. Chem. 2005, 42, 563.
5. [5]
  Zhang, L.-F.; Ni, Z.-H.; Li, D.-Y.; Qin, Z.-H.; Wei, X.-Y. Chin. Chem. Lett. 2012, 23, 281. doi: 10.1016/j.cclet.2011.12.004
6. [6]
  Jonaghani, M. Z.; Boeini, H. Z. Spectrochim. Acta A 2017, 178, 66. doi: 10.1016/j.saa.2017.01.065
7. [7]
  (a) Yoshimura, A.; Zhdankin, V. V. Chem. Rev. 2016, 116, 3328.
  (b) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299.
8. [8]
9. [9]
  (a) Alvarado, J.; Fournier, J.; Zakarian, A. Angew. Chem., Int. Ed. 2016, 55, 11625.
  (b) Zhang, H.; Shen, J.; Cheng, G.; Feng, Y.; Cui, X. Org. Lett. 2018, 20, 664.
  (c) Zhang, X.; Hou, W.; Zhang-Negrerie, D.; Zhao, K.; Du, Y. Org. Lett. 2015, 17, 5252.
  (d) Zheng, Y.; Li, X.; Ren, C.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. J. Org. Chem. 2012, 77, 10353.
  (e) Zhang, N.; Cheng, R.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. J. Org. Chem. 2014, 79, 10581.
10. [10]
  (a) Mariappan, A.; Rajaguru, K.; Roja, S. S.; Muthusubramanian, S.; Bhuvanesh, N. Eur. J. Org. Chem. 2016, 81, 302.
  (b) Downer-Riley, N. K.; Jackson, Y. A. Tetrahedron 2008, 64, 7741.
  (c) Guo, W.-S.; Gong, H.; Zhang, Y.-A.; Wen, L.-R.; Li, M. Org. Lett. 2018, 20, 6394.
  (d) Chinchilla, R.; Nájera, C.; Yus, M. Chem. Rev. 2004, 104, 2667.
  (e) Xie, H.; Cai, J.-H.; Wang, Z.-L.; Huang, H.-W.; Deng, G.-J. Org. Lett. 2016, 18, 2196.
  (f) Wipf, P.; Venkatraman, S. J. Org. Chem. 1996, 61, 8004.
  (g) Kumar, D.; Kumar, N. M.; Chang, K.-H.; Gupta, R.; Shah, K. Bioorg. Med. Chem. Lett. 2011, 21, 5897.
  (h) Bose, D. S.; Idrees, M. J. Org. Chem. 2006, 71, 8261.
11. [11]
  Kumar, D.; Kumar, N. M.; Chang, K.-H.; Gupta, R.; Shah, K. Bioorg. Med. Chem. Lett. 2011, 21, 5897. doi: 10.1016/j.bmcl.2011.07.089
12. [12]
  Liu, T.-B.; Peng, Y.-F. Chin. J. Chem. Educ. 2018, 39, 36 (in Chinese).
1. [1]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
2. [2]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
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]
  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
5. [5]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
6. [6]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
7. [7]
  Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO₂ reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
8. [8]
  Xiting Zhou , Zhipeng Han , Xinlei Zhang , Shixuan Zhu , Cheng Che , Liang Xu , Zhenyu Sun , Leiduan Hao , Zhiyu Yang . Dual Modulation via Ag-Doped CuO Catalyst and Iodide-Containing Electrolyte for Enhanced Electrocatalytic CO₂ Reduction to Multi-Carbon Products: A Comprehensive Chemistry Experiment. University Chemistry, 2025, 40(7): 336-344. doi: 10.12461/PKU.DXHX202412070
9. [9]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
10. [10]
  Jianding LI , Junyang FENG , Huimin REN , Gang LI . Proton conductive properties of a Hf(Ⅳ)-based metal-organic framework built by 2,5-dibromophenyl-4,6-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1094-1100. doi: 10.11862/CJIC.20240464
11. [11]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
12. [12]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
13. [13]
  Zixuan Zhao , Miao Fan . “Carbon” with No “Ester”: A Boundless Journey of CO₂ Transformation. University Chemistry, 2025, 40(7): 213-217. doi: 10.12461/PKU.DXHX202409040
14. [14]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
15. [15]
  Yaping ZHANG , Tongchen WU , Yun ZHENG , Bizhou LIN . Z-scheme heterojunction β-Bi₂O₃ pillared CoAl layered double hydroxide nanohybrid: Fabrication and photocatalytic degradation property. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 531-539. doi: 10.11862/CJIC.20240256
16. [16]
  Runhua Chen , Qiong Wu , Jingchen Luo , Xiaolong Zu , Shan Zhu , Yongfu Sun . 缺陷态二维超薄材料用于光/电催化CO₂还原的基础与展望. Acta Physico-Chimica Sinica, 2025, 41(3): 2308052-. doi: 10.3866/PKU.WHXB202308052
17. [17]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
18. [18]
  Fei Xie , Chengcheng Yuan , Haiyan Tan , Alireza Z. Moshfegh , Bicheng Zhu , Jiaguo Yu . d带中心调控过渡金属单原子负载COF吸附O₂的理论计算研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2407013-. doi: 10.3866/PKU.WHXB202407013
19. [19]
  .
  南开大学师唯/华北电力大学（保定）刘景维：二维配位聚合物中有序的亲锂冠醚位点用于无枝晶锂沉积
  . CCS Chemistry, 2025, 7(0): -.
20. [20]
  Liuyun Chen , Wenju Wang , Tairong Lu , Xuan Luo , Xinling Xie , Kelin Huang , Shanli Qin , Tongming Su , Zuzeng Qin , Hongbing Ji . Soft template-induced deep pore structure of Cu/Al₂O₃ for promoting plasma-catalyzed CO₂ hydrogenation to DME. Acta Physico-Chimica Sinica, 2025, 41(6): 100054-. doi: 10.1016/j.actphy.2025.100054

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(838)
HTML views(55)

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

Metal-Free Rapid Synthesis of 2-Aroylamino Naphtho[1, 2-d]thiazoles

南开大学师唯/华北电力大学（保定）刘景维：二维配位聚合物中有序的亲锂冠醚位点用于无枝晶锂沉积

Metrics

通讯作者: 陈斌, bchen63@163.com