Citation:
Aamer Saeed, Pervaiz Ali Channar, Qasir Iqbal, Jamaluddin Mahar. C-H Arylation using acyl thiourea ligands:Applications in the synthesis of 3,6-diaryl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles[J]. Chinese Chemical Letters,
;2016, 27(01): 37-40.
doi:
10.1016/j.cclet.2015.09.011
-
Synthesis of a series of new 3,6-diaryl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles(5a-o) was achieved by phophine free, C-H arylative cross-coupling of 6-aryl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles(4a-o) with suitably substituted iodoanilines using 1-(2-naphthoyl)-3-(4-bromophenyl)thiourea as a ligand. The requisite triazolothiadiazoles(4a-o) were obtained by the condensation of 4-amino-1,2,4-triazole-3-thiol(3) with suitably substituted aromatic acids in the presence of phosphoryl chloride.
-
-
-
[1]
[1] R.F. Heck, J.P. Nolley Jr., Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides, J. Org. Chem. 37(1972) 2320-2322.
-
[2]
[2] T. Mizoroki, K. Mori, A. Ozaki, Arylation of olefin with aryl iodide catalyzed by palladium, Bull. Chem. Soc. Jpn. 44(1971) 581-587.
-
[3]
[3] C. Shen, P. Zhang, Q. Sun, et al., Recent advances in C-S bond formation via C-H bond functionalization and decarboxylation, Chem. Soc. Rev. 44(2015) 291-314.
-
[4]
[4] X. Cai, B. Xie, Recent advances in nickel-catalyzed C-H bond functionalized reactions, ARKIVOC(i)(2015) 184-211.
-
[5]
[5] Z.Q. Lin, W.Z. Wang, S.B. Yan, Palladium-catalyzed enantioselective CH arylation for the synthesis of P-stereogenic compounds, Angew. Chem. Int. Ed. 54(2015) 6265-6269.
-
[6]
[6] M. Moselage, N. Sauermann, S.C. Richter, et al., C-H alkenylations with alkenyl acetates, phosphates, carbonates, and carbamates by cobalt catalysis at 23℃, Angew. Chem. Int. Ed. 54(2015) 6352-6635.
-
[7]
[7] S. Protti, M. Fagnoni, D. Ravelli, Photocatalytic CH activation by hydrogen-atom transfer in synthesis, ChemCatChem 7(2015) 1516-1523.
-
[8]
[8] X. Sun, Y. Sun, Y. Rao, A gram-scale synthesis of multi-substituted arenes via palladium catalyzed C-H halogenation, Chin. Chem. Lett. 25(2014) 667-669.
-
[9]
[9] L.Y. Liu, Y.Z. Yan, Y.J. Bao, Z.Y. Wang, Efficient synthesis of 2-arylquinazolines via copper-catalyzed dual oxidative benzylic C-H aminations of methylarenes, Chin. Chem. Lett.(2015), http://dx.doi.org/10.1016/j.cclet.2015.07.008.
-
[10]
[10] D. Chen, H. Mo, D. Chen, J. Yang, Direct C-H amination for indole synthesis from NTs-2-styrylaniline derivatives catalyzed by copper salt, Chin. Chem. Lett. 26(2015) 969-972.
-
[11]
[11] D. Yang, Y. Chen, N. Zhu, Sterically bulky thioureas as air-and moisture-stable ligands for Pd-catalyzed Heck reactions of aryl halides, Org. Lett. 6(2004) 1577-1580.
-
[12]
[12] D. Mingji, B. Liang, C. Wang, et al., A novel thiourea ligand applied in the Pdcatalyzed Heck, Suzuki and Suzuki carbonylative reactions, Adv. Synth. Catal. 346(2004) 1669-1673.
-
[13]
[13] S. Keesara, S. Parvathaneni, M.R. Mandapati, N,N'-Mono substituted acyclic thioureas:efficient ligands for the palladium catalyzed Heck reaction of deactivated aryl bromides, Tetrahedron Lett. 55(2014) 6769-6772.
-
[14]
[14] S.M.I. Badr, R.M. Barwa, Synthesis of some new[1,2,4] triazolo[3,4-b][1,3,4] thiadiazines and[1,2,4] triazolo[3,4-b][1,3,4] thiadiazoles starting from 5-nitro-2-furoic acid and evaluation of their antimicrobial activity, Bioorg. Med. Chem. 19(2011) 4506-4512.
-
[15]
[15] R.D. Hunashal, D. Satyanarayana, One pot synthesis of 3-(substituted phenoxymethyl)-6-phenyl/substituted phenoxymethyl-1,2,4-triazolo[3,4-b][1,3,4] thiadiazole derivatives as antimicrobial agents, Int. J. Pharm. Biol. Sci. 3(2012) 183-192.
-
[16]
[16] A. Saeed, S. Ashraf, J.M. White, et al., Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations, Spectrochim. Acta 143(2015) 59-66.
-
[1]
-
-
-
[1]
Entian Cui , Yulian Lu , Zhaoxia Li , Zhilei Chen , Chengyan Ge , Jizhou Jiang . Interfacial B-O bonding modulated S-scheme B-doped N-deficient C3N4/O-doped-C3N5 for efficient photocatalytic overall water splitting. Chinese Chemical Letters, 2025, 36(1): 110288-. doi: 10.1016/j.cclet.2024.110288
-
[2]
Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp3)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
-
[3]
Xuejiao Wang , Suiying Dong , Kezhen Qi , Vadim Popkov , Xianglin Xiang . Photocatalytic CO2 Reduction by Modified g-C3N4. Acta Physico-Chimica Sinica, 2024, 40(12): 2408005-. doi: 10.3866/PKU.WHXB202408005
-
[4]
Liang Ma , Zhou Li , Zhiqiang Jiang , Xiaofeng Wu , Shixin Chang , Sónia A. C. Carabineiro , Kangle Lv . Effect of precursors on the structure and photocatalytic performance of g-C3N4 for NO oxidation and CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100416-100416. doi: 10.1016/j.cjsc.2024.100416
-
[5]
Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C3N4光催化剂及其高效H2O2光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
-
[6]
Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C3N4纳米片用于高效光催化产H2O2. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
-
[7]
Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C3N4/AgI.x.y heterojunction photocatalyst for simultaneous and stoichiometric production of H2 and H2O2 from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
-
[8]
Zhi Zhu , Xiaohan Xing , Qi Qi , Wenjing Shen , Hongyue Wu , Dongyi Li , Binrong Li , Jialin Liang , Xu Tang , Jun Zhao , Hongping Li , Pengwei Huo . Fabrication of graphene modified CeO2/g-C3N4 heterostructures for photocatalytic degradation of organic pollutants. Chinese Journal of Structural Chemistry, 2023, 42(12): 100194-100194. doi: 10.1016/j.cjsc.2023.100194
-
[9]
Qingwang LIU . MoS2/Ag/g-C3N4 Z-scheme heterojunction: Preparation and photocatalytic performance. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 821-832. doi: 10.11862/CJIC.20240148
-
[10]
Kai Han , Guohui Dong , Ishaaq Saeed , Tingting Dong , Chenyang Xiao . Morphology and photocatalytic tetracycline degradation of g-C3N4 optimized by the coal gangue. Chinese Journal of Structural Chemistry, 2024, 43(2): 100208-100208. doi: 10.1016/j.cjsc.2023.100208
-
[11]
Yanghanbin Zhang , Dongxiao Wen , Wei Sun , Jiahe Peng , Dezhong Yu , Xin Li , Yang Qu , Jizhou Jiang . State-of-the-art evolution of g-C3N4-based photocatalytic applications: A critical review. Chinese Journal of Structural Chemistry, 2024, 43(12): 100469-100469. doi: 10.1016/j.cjsc.2024.100469
-
[12]
Min WANG , Dehua XIN , Yaning SHI , Wenyao ZHU , Yuanqun ZHANG , Wei ZHANG . Construction and full-spectrum catalytic performance of multilevel Ag/Bi/nitrogen vacancy g-C3N4/Ti3C2Tx Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477
-
[13]
Jianyu Qin , Yuejiao An , Yanfeng Zhang . In Situ Assembled ZnWO4/g-C3N4 S-Scheme Heterojunction with Nitrogen Defect for CO2 Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408002-. doi: 10.3866/PKU.WHXB202408002
-
[14]
Heng Chen , Longhui Nie , Kai Xu , Yiqiong Yang , Caihong Fang . 两步焙烧法制备大比表面积和结晶性增强超薄g-C3N4纳米片及其高效光催化产H2O2. Acta Physico-Chimica Sinica, 2024, 40(11): 2406019-. doi: 10.3866/PKU.WHXB202406019
-
[15]
Hong-Tao Ji , Yu-Han Lu , Yan-Ting Liu , Yu-Lin Huang , Jiang-Feng Tian , Feng Liu , Yan-Yan Zeng , Hai-Yan Yang , Yong-Hong Zhang , Wei-Min He . Nd@C3N4-photoredox/chlorine dual catalyzed synthesis and evaluation of antitumor activities of 4-alkylated sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110568-. doi: 10.1016/j.cclet.2024.110568
-
[16]
Xin Jiang , Han Jiang , Yimin Tang , Huizhu Zhang , Libin Yang , Xiuwen Wang , Bing Zhao . g-C3N4/TiO2-X heterojunction with high-efficiency carrier separation and multiple charge transfer paths for ultrasensitive SERS sensing. Chinese Chemical Letters, 2024, 35(10): 109415-. doi: 10.1016/j.cclet.2023.109415
-
[17]
Xiaoming Fu , Haibo Huang , Guogang Tang , Jingmin Zhang , Junyue Sheng , Hua Tang . Recent advances in g-C3N4-based direct Z-scheme photocatalysts for environmental and energy applications. Chinese Journal of Structural Chemistry, 2024, 43(2): 100214-100214. doi: 10.1016/j.cjsc.2024.100214
-
[18]
Guangming YIN , Huaiyao WANG , Jianhua ZHENG , Xinyue DONG , Jian LI , Yi'nan SUN , Yiming GAO , Bingbing WANG . Preparation and photocatalytic degradation performance of Ag/protonated g-C3N4 nanorod materials. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1491-1500. doi: 10.11862/CJIC.20240086
-
[19]
Shengkai Li , Yuqin Zou , Chen Chen , Shuangyin Wang , Zhao-Qing Liu . Defect engineered electrocatalysts for C–N coupling reactions toward urea synthesis. Chinese Chemical Letters, 2024, 35(8): 109147-. doi: 10.1016/j.cclet.2023.109147
-
[20]
Yingqi BAI , Hua ZHAO , Huipeng LI , Xinran REN , Jun LI . Perovskite LaCoO3/g-C3N4 heterojunction: Construction and photocatalytic degradation properties. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 480-490. doi: 10.11862/CJIC.20240259
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(704)
- HTML views(18)