A KHSO4 mediated facile synthesis of 2-amino-1,3,4-oxadiazole derivatives

被引:10
作者
Long, Binyu [1 ,2 ]
Tian, Binghua [1 ]
Tang, Qiang [1 ,2 ]
Hu, Xiangnan [1 ,2 ]
Han, Lei [1 ]
Wang, Zifan [1 ]
Wang, Chenyu [1 ]
Wu, Yue [1 ]
Yu, Yu [1 ]
Gan, Zongjie [1 ]
机构
[1] Chongqing Med Univ, Dept Med Chem, Coll Pharm, Chongqing 400016, Peoples R China
[2] Chongqing Med Univ, Chongqing Res Ctr Pharmaceut Engn, Chongqing 400016, Peoples R China
基金
中国国家自然科学基金;
关键词
2-amino-1,3,4-thiadiazoles; KHSO4; Cyclodesulfurization; EFFICIENT SYNTHESIS; 1,3,4-OXADIAZOLE; DESIGN; BEARING; REAGENT; MILD;
D O I
10.1016/j.tet.2021.132382
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel, efficient and mild KHSO4 mediated synthesis for 2-amino-1,3,4-oxadiazoles has been established via the cyclodesulfurization of benzoylhydrazine and isothiocyanate derivatives in one pot. The reactions proceeded smoothly at room temperature and produced corresponding products in moderate to good yields. This protocol also showed good functional group tolerance. (C) 2021 Elsevier Ltd. All rights reserved.
引用
收藏
页数:8
相关论文
共 50 条
  • [21] Synthesis and Bioactivities of Novel 1,3,4-oxadiazole Derivatives Containing Pyridine Moiety
    Sun, Guo-Xiang
    Shi, Yan-Xia
    Sun, Zhao-Hui
    Yang, Ming-Yan
    Wu, Hong-Ke
    Weng, Jian-Quan
    Tan, Cheng-Xia
    Liu, Xing-Hai
    Li, Bao-Ju
    Zhang, Yong-Gang
    [J]. LETTERS IN DRUG DESIGN & DISCOVERY, 2014, 11 (09) : 1119 - 1123
  • [22] Synthesis and Anticancer Evaluation of Amide Derivatives of 1,3,4-Oxadiazole Linked with Benzoxazole
    Ravinaik, B.
    Ramachandran, D.
    Rao, M. V. Basaveswara
    [J]. RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2019, 89 (05) : 1003 - 1008
  • [23] Synthesis of some novel 1,3,4-oxadiazole derivatives and evaluation of their antimicrobial activity
    Tok, Fatih
    Kaya, Murat
    Karaca, Hulya
    Kocyigit-Kaymakcioglu, Bedia
    [J]. SYNTHETIC COMMUNICATIONS, 2022, 52 (06) : 926 - 935
  • [24] Synthesis and Fungicidal Activity of 1,3,4-Oxadiazole Derivatives Containing Pyrazole Moiety
    Sun, Nabo
    Tong, Jianying
    Wu, Hongke
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2013, 33 (01) : 101 - 105
  • [25] Synthesis and antiviral activity of 2-substituted methylthio-5-(4-amino-2-methylpyrimidin-5-yl)-1,3,4-oxadiazole derivatives
    Wu, Wenneng
    Chen, Qin
    Tai, Anqi
    Jiang, Guangqi
    Ouyang, Guiping
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (10) : 2243 - 2246
  • [26] Synthesis and bioactivities of novel 2-(thioether/sulfone)-5-pyrazolyl-1,3,4-oxadiazole derivatives
    Zheng, Yu-Tao
    Zhang, Teng-Teng
    Wang, Pei-Yi
    Wu, Zhi-Bing
    Zhou, Lei
    Ye, Yi-Qiang
    Zhou, Xiang
    He, Ming
    Yang, Song
    [J]. CHINESE CHEMICAL LETTERS, 2017, 28 (02) : 253 - 256
  • [27] Hydrazides: An Important Tool for the Synthesis of 1,3,4-Oxadiazole
    Tripathi, Shrishti
    Kumar, Rajnish
    Mazumder, Avijit
    Kukreti, Neelima
    Kumar, Arvind
    Singh, Gurvinder
    [J]. CURRENT ORGANIC CHEMISTRY, 2025, 29 (08) : 658 - 668
  • [28] Anti-Cancer Activity of Derivatives of 1,3,4-Oxadiazole
    Glomb, Teresa
    Szymankiewicz, Karolina
    Swiatek, Piotr
    [J]. MOLECULES, 2018, 23 (12):
  • [29] Synthesis, Biological Evaluation and Docking Studies of 1,3,4-oxadiazole Fused Benzothiazole Derivatives for Anticancer Drugs
    Subramanyam, Madala
    Sreenivasulu, Reddymasu
    Gundla, Rambabu
    Rao, Mandava V. B.
    Rao, Koya Prabhakara
    [J]. LETTERS IN DRUG DESIGN & DISCOVERY, 2018, 15 (12) : 1299 - 1307
  • [30] SYNTHESIS AND CHARACTERIZATION OF NEW THIAZOLYL 1,3,4-OXADIAZOLE AND 1,2,4-TRIAZOLE DERIVATIVES
    Darekar, Nirmala R.
    Dengale, Sujata G.
    Sasane, Kulbhushan A.
    Patil, Shripad M.
    Akolkar, Hemantkumar N.
    [J]. HETEROCYCLIC LETTERS, 2024, 14 (02):