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
  • [1] An efficient one-pot synthesis of 3-substituted-5-amino1,2,4-thiadiazoles from isothiocyanates and amidines
    Wu, Yong-Jin
    Zhang, Yunhui
    TETRAHEDRON LETTERS, 2008, 49 (18) : 2869 - 2871
  • [2] One-Pot Synthesis of 5-Acyl-2-amino-1,3,4-thiadiazoles
    Lindstrom, Johan
    Hallberg, Jesper
    SYNTHESIS-STUTTGART, 2012, 44 (19): : 3059 - 3062
  • [3] One-pot synthesis of bis(amino)-1,2,4-thiadiazoles via direct SNAr
    Beeley, Howard A.
    Degorce, Sebastien
    Harris, Craig S.
    Lecoq, Jonathan
    Morgentin, Remy
    Perkins, David
    TETRAHEDRON LETTERS, 2013, 54 (08) : 788 - 791
  • [4] Catalyst-Free One-Pot Access to 3-Pyrazolylisoindolinone Derivatives
    Che, Fengfeng
    Fu, Zhijie
    Shen, Tianhua
    Lin, Yan
    Song, Qingbao
    SYNTHESIS-STUTTGART, 2015, 47 (21): : 3403 - 3411
  • [5] Regioselectivity of alkylation of 3-substituted 5-amino-1,2,4-thiadiazoles
    Khakimov, M
    Ambartsumova, RF
    Tashkhodzhaev, B
    Antipin, MY
    Shakhidoyatov, KM
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2001, (08): : 1095 - 1100
  • [6] Regioselectivity of alkylation of 3-substituted 5-amino-1,2,4-thiadiazoles
    Khakimov M.
    Ambartsumova R.F.
    Tashkhodzhaev B.
    Antipin M.Yu.
    Shakhidoyatov Kh.M.
    Chemistry of Heterocyclic Compounds, 2001, 37 (08) : 1005 - 1010
  • [7] Copper-catalyzed synthesis of 3-substituted-5-amino-1,2,4-thiadiazoles via intramolecular N-S bond formation
    Kim, Ha-Young
    Kwak, Se Hun
    Lee, Gee-Hyung
    Gong, Young-Dae
    TETRAHEDRON, 2014, 70 (45) : 8737 - 8743
  • [8] A rapid one-pot synthesis of 5-substituted-2-mercapto-1,3,4-thiadiazoles using microwaves
    Kidwai, M
    Bhushan, KR
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1998, 37 (05): : 427 - 428
  • [9] A convenient four-component one-pot synthesis of 2-amino-1,3,4-thiadiazoles in water
    Peng Liu
    Ao-Ze Su
    Yuan-Qiang Wang
    Ze-Mei Ge
    Tie-Ming Cheng
    Run-Tao Li
    Molecular Diversity, 2014, 18 : 737 - 743
  • [10] A convenient four-component one-pot synthesis of 2-amino-1,3,4-thiadiazoles in water
    Liu, Peng
    Su, Ao-Ze
    Wang, Yuan-Qiang
    Ge, Ze-Mei
    Cheng, Tie-Ming
    Li, Run-Tao
    MOLECULAR DIVERSITY, 2014, 18 (04) : 737 - 743
12345