Ring Opening of N-Sulfonyl Aziridines by Amines in Silica-Water

被引：4
|
作者：
Li, Tiantian [1 ]
Ma, Xiaosi [1 ]
Qi, Junmei [1 ]
Sun, Feifei [1 ,2 ]
Ma, Ning [1 ,2 ]
机构：
[1] Tianjin Univ, Sch Sci, Dept Chem, Tianjin 300072, Peoples R China
[2] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300072, Peoples R China
来源：
CHINESE JOURNAL OF CHEMISTRY | 2014年 / 32卷 / 11期
基金：
中国国家自然科学基金;
关键词：
aziridines; ring opening; amines; silica gel; reactions in water; ORGANIC-SYNTHESIS; EFFICIENT SYNTHESIS; FACILE SYNTHESIS; SOLVENT-FREE; CHEMISTRY; EPOXIDES; SALTS; SULFONYLCYCLOTHIOUREAS; TRIBUTYLPHOSPHINE; ALCOHOLS;
D O I：
10.1002/cjoc.201400300
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Ring opening reactions of N-sulfonyl aziridines by primary and secondary amines in silica gel (SG)-water system were achieved, which provided a mild, practical and environmentally benign method to synthesize mono- and bis-sulfonyl substituted amines. When primary and secondary amines were used in excess, they reacted with N-sulfonyl aziridines smoothly at room temperature, mainly affording 1:1 ring opening products. Reactions of primary amines with 2 equiv. of aziridines produced 2:1 ring opening products. Some 1:1 products can be cyclized with CS2 to synthesize N-sulfonyl cyclothioureas also in water.
引用
收藏
页码：1135 / 1142
页数：8
相关论文
共 50 条
  • [41] Practical synthesis of chiral β-telluro amines by ring-opening reaction of aziridines
    Vargas, Fabricio
    Comasseto, Joao V.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (01) : 122 - 126
  • [42] Ring-opening reaction of aziridines with amines under the influence of dimethyl sulfoxide
    Isobe, Toshihiro
    Oriyama, Takeshi
    TETRAHEDRON LETTERS, 2016, 57 (26) : 2849 - 2852
  • [43] Mild and efficient method for regioselective ring opening of aziridines with amines by bismuth trichloride
    Swamy, NR
    Venkateswarlu, Y
    SYNTHETIC COMMUNICATIONS, 2003, 33 (04) : 547 - 554
  • [44] Nickel-Catalyzed Enantioselective α-Alkenylation of N-Sulfonyl Amines: Modular Access to Chiral α-Branched Amines
    Li, Lun
    Liu, Yu-Cheng
    Shi, Hang
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (11) : 4154 - 4161
  • [45] Synthesis of Metallocene Analogues of the Phenethylamine and Tetrahydroisoquinoline Scaffolds via Regioselective Ring Opening of 2-Aryl-N-sulfonyl Aziridines
    Gonzalez-Pelayo, Silvia
    Bernardo, Olaya
    Borge, Javier
    Lopez, Luis A.
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (03) : 819 - 825
  • [46] Cobalt-catalyzed divergent functionalization of N-sulfonyl amines via β-carbon elimination
    Lun Xu
    Hang Shi
    Science China Chemistry, 2022, 65 : 2214 - 2218
  • [47] Cobalt-catalyzed divergent functionalization of N-sulfonyl amines via β-carbon elimination
    Lun Xu
    Hang Shi
    Science China(Chemistry), 2022, 65 (11) : 2214 - 2218
  • [48] Cobalt-catalyzed divergent functionalization of N-sulfonyl amines via β-carbon elimination
    Xu, Lun
    Shi, Hang
    SCIENCE CHINA-CHEMISTRY, 2022, 65 (11) : 2214 - 2218
  • [49] Well-Defined Poly(Ester Amide)-Based Homo- and Block Copolymers by One-Pot Organocatalytic Anionic Ring-Opening Copolymerization of N-Sulfonyl Aziridines and Cyclic Anhydrides
    Xu, Jiaxi
    Hadjichristidis, Nikos
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (13) : 6949 - 6954
  • [50] Cobalt-catalyzed divergent functionalization of N-sulfonyl amines via β-carbon elimination
    Lun Xu
    Hang Shi
    Science China(Chemistry) , 2022, (11) : 2214 - 2218
12345