Sulfur-Containing 1,2,3-Triazoles: Synthesis and Properties

被引:5
作者
Peng, Lifen [1 ,2 ]
Chen, Jiayi [1 ]
Chen, Yi [3 ]
Lu, Hao [2 ]
Okuda, Yasuhiro [4 ]
Tang, Zilong [1 ]
Orita, Akihiro [4 ]
Qiu, Renhua [2 ]
Yin, Shuang-Feng [2 ]
机构
[1] Hunan Univ Sci, Sch Chem & Chem Engn, Key Lab Theoret Organ Chem & Funct Mol,Minist Educ, Hunan Prov Key Lab Controllable Preparat & Funct A, Xiangtan 411201, Hunan, Peoples R China
[2] Hunan Univ, Coll Chem & Chem Engn, Adv Catalyt Engn Res Ctr,Minist Educ, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Peoples R China
[3] Hunan Univ Chinese Med, Sch Med, Dept Physiol, Changsha 410208, Hunan, Peoples R China
[4] Okayama Univ Sci, Dept Appl Chem, 1-1 Ridai Cho,Kita Ku, Okayama 7000005, Japan
基金
日本学术振兴会;
关键词
sulfur-containing 1,2,3-triazole; sulfanyl-1,2,3-triazole; sulfonyl-1,2,3-triazole; CuAAC; bioactivity; AZIDE-ALKYNE CYCLOADDITION; CLICK CHEMISTRY; CATALYZED CYCLOADDITION; 1,3-DIPOLAR CYCLOADDITION; REGIOSELECTIVE SYNTHESIS; SULFONYL AZIDES; AQUEOUS-MEDIA; INHIBITORS; COMPLEXES; MILD;
D O I
10.1002/ejoc.202301146
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sulfur-containing 1,2,3-triazoles display bioactivities like antidepressant, antifungal activity, antitumor, etc. Numerous approaches have been established to form sulfur-containing 1,2,3-triazoles. 4-Sulfanyl- and 5-sulfanyl-1,2,3-triazoles were produced by metal-catalyzed azide-alkyne cycloaddition (AAC), etc. N-Sulfonyl-1,2,3-triazoles were generated via the reaction of acetylides with sulfonyl azides, CuAAC. 4-Sulfonyl-1,2,3-triazoles were produced through [3+2] cycloaddition and reaction of azide with bromovinylsulfonyl fluoride. Although 5-sulfonyl-1,2,3-triazoles were formed successfully via RuAAC, their synthetic approaches were very limited. 1-Phosphinyl-2-sulfanylethynes were suitable substances to access sulfur- and phosphorus-containing triazoles. In this review, the synthesis and properties of sulfur-containing 1,2,3-triazoles were highlighted. Initially, the properties of organosulfurs, 1,2,3-triazoles and sulfur-containing 1,2,3-triazoles were briefly introduced. After stating the general procedures to construct 1,2,3-triazole skeleton, the synthetic approaches and properties of sulfur-involved 1,2,3-triazoles were sorted and described in details. According to different kinds of sulfur-containing 1,2,3-triazoles, synthetic methods and features of 4-sulfanyl-1,2,3-triazoles, 5-sulfanyl-1,2,3-triazoles, N-sulfonyl-1,2,3-triazoles, 4-sulfonyl-1,2,3-triazoles, 5-sulfonyl-1,2,3-triazoles, sulfur- and heteroatom-containing 1,2,3-triazoles were summarized. Sulfur-containing 1,2,3-triazoles display bioactivities. Numerous approaches have been established to form sulfur-containing 1,2,3-triazoles. In this review, the synthesis and properties of sulfur-containing 1,2,3-triazoles, including 4-sulfanyl-1,2,3-triazoles, 5-sulfanyl-1,2,3-triazoles, N-sulfonyl-1,2,3-triazoles, 4-sulfonyl-1,2,3-triazoles, 5-sulfonyl-1,2,3-triazoles, sulfur- and heteroatom-containing 1,2,3-triazoles, were highlighted.image
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页数:21
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