Catalyst-free, one-pot strategy to access 3-substituted-5-amino-1,2,4-thiadiazoles in water

被引：3
|
作者：
Nagaraju, Chaithra [1 ]
Ashok, Swarup Hassan [2 ]
Narayana, Yatheesh [1 ]
Nagarakere, Sandhya C. [3 ]
Kempegowda, Mantelingu [1 ]
Kanchugarkoppal, Rangappa S. [1 ]
机构：
[1] Univ Mysore, Synthet Lab, DOS Chem, Mysuru, India
[2] BNM Inst Technol, Dept Chem, Bangalore, Karnataka, India
[3] St Philomenas Coll, PG Dept Chem, Mysuru, India
来源：
SYNTHETIC COMMUNICATIONS | 2021年 / 51卷 / 23期
关键词：
Amidoximes; catalyst-free; isothiacyanates; S-N bond formation; 1; 2; 4-thiadiazole; BIOLOGICAL EVALUATION; ALLOSTERIC MODULATOR; 1,2,4-THIADIAZOLES; 1,2,4-OXADIAZOLES; DERIVATIVES; SCH-202676; INHIBITORS; SOLVENT;
D O I：
10.1080/00397911.2021.1986840
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A protocol has been devised for the synthesis of 3-substituted 5-amino-1,2,4-thiadiazoles utilizing isothiocyanates, amidoximes and water as an eco-friendly solvent. The strategy involves consecutive C-N and S-N bonds formation in a one-pot reaction under catalyst-free conditions. Operational simplicity, low cost, broad substrate scope and readily available starting materials are the main features of this protocol.
引用
收藏
页码：3610 / 3619
页数：10
相关论文
共 50 条
  • [41] One-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazoles under ultrasonic irradiation
    Ying Jun Li Ya Zhen Sun Yong Ting Xu Li Ping Wen Ni Bo Hou Xiao Xiao Sun College of Chemistry and Chemical Engineering
    Chinese Chemical Letters, 2007, (09) : 1047 - 1048
  • [42] A facile synthesis of 3-substituted 5-oxo-1,2,4-thiadiazoles from amidoximes
    Kohara, Y
    Kubo, K
    Imamiya, E
    Naka, T
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (06) : 1419 - 1423
  • [43] ANTIFUNGAL AGENTS .I. 5-SUBSTITUTED-3-(TRICHLOROMETHYL)-1,2,4-THIADIAZOLES
    NARAYANAN, VL
    BERNSTEIN, J
    WILLIAMS, J
    JOURNAL OF PHARMACEUTICAL SCIENCES, 1966, 55 (02) : 217 - +
  • [44] THIADIAZOLES .8. 3-ALKYL(OR ARYL)-5-ALKYL(OR ARYL)-AMINO-1,2,4-THIADIAZOLES
    KURZER, F
    TERTIUK, W
    JOURNAL OF THE CHEMICAL SOCIETY, 1959, (SEP-O): : 2851 - 2857
  • [45] Rapid, green, and catalyst-free one-pot three-component syntheses of 5-substituted 1H-tetrazoles in magnetized water
    Bakherad, Mohammad
    Doosti, Rahele
    Keivanloo, Ali
    Gholizadeh, Mostafa
    Jadidi, Khosrow
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2017, 14 (12) : 2591 - 2597
  • [46] Rapid, green, and catalyst-free one-pot three-component syntheses of 5-substituted 1H-tetrazoles in magnetized water
    Mohammad Bakherad
    Rahele Doosti
    Ali Keivanloo
    Mostafa Gholizadeh
    Khosrow Jadidi
    Journal of the Iranian Chemical Society, 2017, 14 : 2591 - 2597
  • [47] Interaction of 2-Amino-1,3,4-thiadiazoles with 1,2,4-Triazine-5-carbonitriles
    Krinochkin, A. P.
    Shtaitz, Ya K.
    Kudryashova, E. A.
    Ladin, E. D.
    Kopchuk, D. S.
    Zyryanov, G., V
    Shafran, Yu M.
    Nosova, E., V
    Chupakhin, O. N.
    DOKLADY CHEMISTRY, 2022, 504 (01) : 79 - 82
  • [48] One-pot gram-scale synthesis of γ-hydroxybutenolides through catalyst-free annulation of α-amino acids with α-keto acids in water
    He, Zhiqing
    Fang, Fang
    Lv, Jianguang
    Zhang, Jianmin
    TETRAHEDRON LETTERS, 2017, 58 (11) : 1034 - 1036
  • [49] External oxidant-free electrooxidative intramolecular S-N bond formation for one-pot synthesis for 3,5-disubstituted 1,2,4-thiadiazoles
    Zhong, Qihao
    Sheng, Shouri
    Chen, Junmin
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2020, 195 (12) : 988 - 993
  • [50] Interaction of 2-Amino-1,3,4-thiadiazoles with 1,2,4-Triazine-5-carbonitriles
    A. P. Krinochkin
    Ya. K. Shtaitz
    E. A. Kudryashova
    E. D. Ladin
    D. S. Kopchuk
    G. V. Zyryanov
    Yu. M. Shafran
    E. V. Nosova
    O. N. Chupakhin
    Doklady Chemistry, 2022, 504 : 79 - 82
12345