Metal-Free Direct Synthesis of N-Sulfonyl Amidines from Thioamides and Electron Deficient N-Sulfonylamides

被引:0
|
作者
Vankar, Jigarkumar K. [1 ]
Tothadi, Srinu [2 ]
Gururaja, Guddeangadi N. [1 ]
机构
[1] Cent Univ Gujarat, Sch Chem Sci, Gandhinagar 382030, India
[2] CSIR Cent Salt & MarineChem Res Inst, Bhavnagar 364002, India
关键词
ROTATIONAL BARRIER; COUPLING REACTION; 3-COMPONENT; AZIDES; INTERCEPTION; ALKYNE; SALTS;
D O I
10.1002/ejoc.202400776
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A metal-free, efficient synthesis of N-sulfonyl amidines has been demonstrated from easily accessible thioamides and electron-deficient sulfonyl amides. The amidation reaction is facile at room temperature with low sulfonyl amide loading. The reaction with thioamides is illustrated with various thioamides and electron-deficient sulfonyl amides with broad substrate scope. The utility of N-sulfonyl amidine synthesis is validated with late-stage drug functionalization.
引用
收藏
页数:6
相关论文
共 50 条
  • [21] Direct Synthesis of Enolizable N-Sulfonyl Ketimines Under Microwave Irradiation
    Ortiz, Pablo
    Collados, Juan F.
    Harutyunyan, Syuzanna R.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (07) : 1247 - 1250
  • [22] EFFICIENT SYNTHESIS OF N-SULFONYL β-ARYLMETHYLALANINATES FROM SERINE VIA RING OPENING OF N-SULFONYL AZIRIDINE-2-CARBOXYLATE
    Chaudhari, Prashant
    Bari, Sanjay
    SYNTHETIC COMMUNICATIONS, 2015, 45 (03) : 401 - 412
  • [23] Metal Free, Microwave Assisted Preparation of N-Sulfonyl and N-Sulfinyl lmines and Imidates
    Verrier, Charlie
    Carret, Sebastien
    Poisson, Jean-Francois
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2018, 6 (07): : 8563 - 8569
  • [24] Synthesis of N-Sulfonyl Amidines and 1,3,4-Oxadiazoles through Electrochemical Activation of DMF
    Mahanty, Kingshuk
    Halder, Atreyee
    De Sarkar, Suman
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (01) : 96 - 103
  • [25] Interception of amide ylides with sulfonamides: synthesis of (E)-N-sulfonyl amidines catalyzed by Zn(OTf)2
    Chen, Jijun
    Long, Wenhao
    Fang, Shangwen
    Yang, Yonggang
    Wan, Xiaobing
    CHEMICAL COMMUNICATIONS, 2017, 53 (99) : 13256 - 13259
  • [26] Metal-free synthesis of N-sulfonylformamidines via skeletal reconstruction of sulfonyl oximonitriles
    Li, Feng
    Wu, Ziyan
    Wang, Jingjing
    Zhang, Siyuan
    Yu, Jiaxin
    Yuan, Zhen
    Liu, Jingya
    Shen, Renzeng
    Zhou, Yao
    Liu, Lantao
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (03) : 627 - 632
  • [27] Addition of a carbamoylsilane to N-sulfonylimines: direct synthesis of α-(N-sulfonyl)amino-N-methoxymethyl-N-methylamides
    Liu, Hui
    Guo, Qilin
    Chen, Jianxin
    TETRAHEDRON LETTERS, 2015, 56 (42) : 5747 - 5751
  • [28] Two-step synthesis of N-sulfonyl aziridines from epoxides
    Huang, Jianhui
    O'Brien, Peter
    Synthesis, 2006, (03) : 425 - 434
  • [29] Transition metal-free, chemoselective arylation of thioamides yielding aryl thioimidates or N-aryl thioamides
    Villo, Piret
    Kervefors, Gabriella
    Olofsson, Berit
    CHEMICAL COMMUNICATIONS, 2018, 54 (64) : 8810 - 8813
  • [30] Two-step synthesis of N-sulfonyl aziridines from epoxides
    Huang, JH
    O'Brien, P
    SYNTHESIS-STUTTGART, 2006, (03): : 425 - 434