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
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 27卷 / 45期
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
  • [1] Mechanochemical Metal-free N-Sulfonyl Transfer Reaction: Expedient Synthesis of N-Sulfonyl Amidines
    Guha, Souvik
    Maheshwari, Sanjana
    Ravva, Mahesh
    Jacob, Jesni
    Yadav, Shalini
    Sen, Subhabrata
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (10)
  • [2] Mechanochemical Metal-free N-Sulfonyl Transfer Reaction: Expedient Synthesis of N-Sulfonyl Amidines
    Guha, Souvik
    Maheshwari, Sanjana
    Ravva, Mahesh K.
    Jacob, Jesni M.
    Yadav, Shalini
    Sen, Subhabrata
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023,
  • [3] Regioselective synthesis of heterocyclic N-sulfonyl amidines from heteroaromatic thioamides and sulfonyl azides
    Ilkin, Vladimir
    Berseneva, Vera
    Beryozkina, Tetyana
    Glukhareva, Tatiana
    Dianova, Lidia
    Dehaen, Wim
    Seliverstova, Eugenia
    Bakulev, Vasiliy
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 2937 - 2947
  • [4] Advances in the Synthesis of N-Sulfonyl Amidines
    Zheng, Xixi
    Liu, Yunyun
    Wan, Jie-Ping
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (07) : 1891 - 1900
  • [5] N-Sulfonyl acetylketenimine as a highly reactive intermediate for the synthesis of N-sulfonyl amidines
    Yang, Weiguang
    Huang, Dayun
    Zeng, Xiaobao
    Luo, Dongping
    Wang, Xinyan
    Hu, Yuefei
    CHEMICAL COMMUNICATIONS, 2018, 54 (59) : 8222 - 8225
  • [6] Metal-Free Direct Access to N-Sulfonyl Amidines from Sulfonamides and Secondary Amines Involving Tandem C-N Bond Formations
    Nishad, Chandra Shekhar
    Haldar, Krishna Kanta
    Banerjee, Biplab
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (17): : 11644 - 11655
  • [7] Metal-free synthesis of N-sulfonyl imines from benzyl alcohol derivatives and iminoiodinanes via mechanochemistry
    Guha, Souvik
    Bhattacharya, Ritwik
    Jacob, Jesni
    Ravva, Mahesh
    Sen, Subhabrata
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (27) : 5592 - 5600
  • [8] Synthesis of N-Sulfonyl Amidines and Acyl Sulfonyl Ureas from Sulfonyl Azides, Carbon Monoxide, and Amides
    Chow, Shiao Y.
    Odell, Luke R.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (05): : 2515 - 2522
  • [9] Transition metal- and catalyst-free one-pot green method for the synthesis of N-sulfonyl amidines via direct reaction of sulfonyl azides with amines
    Kaboudin, Babak
    Torabi, Saeed
    Kazemi, Foad
    Aoyama, Hiroshi
    RSC ADVANCES, 2020, 10 (45) : 26701 - 26708
  • [10] Catalyst- and Additive-Free Direct Synthesis of N-Sulfonyl Guanidines
    Maierhaba, Julaiti
    Bulunuer, Yusan
    Abudureheman, Wusiman
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (04) : 1276 - 1283
12345