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 shu

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

1.
Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan

Corresponding author: Aamer Saeed,
Received Date: 17 June 2015
Available Online: 5 August 2015

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.
- [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazoles,
- Acyl thiourea,
- C-H arylative coupling,
- N,N-Dimethylacetamide
1. [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]
  [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]
  [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]
  [4] X. Cai, B. Xie, Recent advances in nickel-catalyzed C-H bond functionalized reactions, ARKIVOC(i)(2015) 184-211.
5. [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]
  [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]
  [7] S. Protti, M. Fagnoni, D. Ravelli, Photocatalytic CH activation by hydrogen-atom transfer in synthesis, ChemCatChem 7(2015) 1516-1523.
8. [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  Qiong-Hui Peng , Ning-Bo Li , Jia-Cheng Hou , Cai-Jun He , Ya-Xin Yang , Chun-Lin Zhuang , Li-Juan Ou , Mei Yuan , Wei-Min He . Nd@g-C₃N₄ dual-functional photosynthesis and antitumor activities of 3-fluoroalkylated quinoxalin-2(1H)-ones. Chinese Chemical Letters, 2025, 36(12): 111402-. doi: 10.1016/j.cclet.2025.111402
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  Xuejiao Wang , Suiying Dong , Kezhen Qi , Vadim Popkov , Xianglin Xiang . Photocatalytic CO₂ Reduction by Modified g-C₃N₄. Acta Physico-Chimica Sinica, 2024, 40(12): 2408005-0. doi: 10.3866/PKU.WHXB202408005
7. [7]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . Molten Intermediate Transportation-Oriented Synthesis of Amino-Rich g-C₃N₄ Nanosheets for Efficient Photocatalytic H₂O₂ Production. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-0. doi: 10.3866/PKU.WHXB202406021
8. [8]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . Simultaneously Improving Inter-Plane Crystallization and Incorporating K Atoms in g-C₃N₄ Photocatalyst for Highly-Efficient H₂O₂ Photosynthesis. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-0. doi: 10.3866/PKU.WHXB202406005
9. [9]
  Zheng Liu , Yuqing Bian , Graham Dawson , Jiawei Zhu , Kai Dai . Rational constructing of Zn_0.5Cd_0.5S-diethylenetriamine/g-C₃N₄ S-scheme heterojunction with enhanced photocatalytic H₂O₂ production. Chinese Chemical Letters, 2025, 36(9): 111272-. doi: 10.1016/j.cclet.2025.111272
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  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
15. [15]
  Haitao Wang , Lianglang Yu , Jizhou Jiang , Arramel , Jing Zou . S-Doping of the N-Sites of g-C₃N₄ to Enhance Photocatalytic H₂ Evolution Activity. Acta Physico-Chimica Sinica, 2024, 40(5): 2305047-0. doi: 10.3866/PKU.WHXB202305047
16. [16]
  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/Ti₃C₂T_x Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477
17. [17]
  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): 2408002-0. doi: 10.3866/PKU.WHXB202408002
18. [18]
  Huahong ZHANG , Yang ZHAO , Rui NING , Shuixing WU , Xiaopeng ZHANG . Coordination equilibrium between cyclometalated Pt(Ⅱ) complexs [Pt(κ³-N^C^N′)(CNXyl)]Cl and [Pt(κ²-N^C^N′)(CNXyl)Cl]. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1840-1850. doi: 10.11862/CJIC.20250136
19. [19]
  Qi Wu , Changhua Wang , Yingying Li , Xintong Zhang . Enhanced photocatalytic synthesis of H₂O₂ by triplet electron transfer at g-C₃N₄@BN van der Waals heterojunction interface. Acta Physico-Chimica Sinica, 2025, 41(9): 100107-0. doi: 10.1016/j.actphy.2025.100107
20. [20]
  Heng Chen , Longhui Nie , Kai Xu , Yiqiong Yang , Caihong Fang . Remarkable Photocatalytic H₂O₂ Production Efficiency over Ultrathin g-C₃N₄ Nanosheet with Large Surface Area and Enhanced Crystallinity by Two-Step Calcination. Acta Physico-Chimica Sinica, 2024, 40(11): 2406019-0. doi: 10.3866/PKU.WHXB202406019

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1142)
HTML views(32)

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