Direct synthesis of carbamates, thiocarbamates, and ureas from Boc-protected amines: a sustainable and efficient approach

被引:0
|
作者
Li, Wanyong [1 ]
Lv, Mengting [1 ]
Luo, Xiaolin [1 ]
Wang, Zhouyu [1 ,2 ]
Song, Qiao [1 ,2 ]
Yu, Xiaoqi [1 ,2 ]
机构
[1] Xihua Univ, Dept Chem, Chengdu 610039, Peoples R China
[2] Xihua Univ, Asymmetr Synth & Chiral Technol Key Lab Sichuan Pr, Chengdu 610039, Peoples R China
基金
中国国家自然科学基金;
关键词
ONE-POT SYNTHESIS; ANTIMICROBIAL ACTIVITY; ARYL;
D O I
10.1039/d4ra03683b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the quest for sustainable and efficient synthetic methodologies within medicinal chemistry, the synthesis of carbamates and their derivatives holds a pivotal role due to their widespread application in bioactive compounds. This investigation unveils a novel methodology for the straightforward transformation of Boc-protected amines into carbamates, thiocarbamates, and ureas, utilizing tert-butoxide lithium as the sole base. This approach effectively obviates the necessity for hazardous reagents and metal catalysts, presenting marked enhancements compared to traditional synthetic pathways. Notably, the method demonstrates facile scalability to gram-level production. This study contributes to the advancement of sustainable synthetic methodologies, offering a more benign and efficient alternative for the synthesis of key chemical intermediates with implications for broad pharmaceutical and agrochemical applications. This investigation unveils a novel methodology for the straightforward transformation of Boc-protected amines into carbamates, thiocarbamates, and ureas, utilizing tert-butoxide lithium as the sole base.
引用
收藏
页码:20656 / 20659
页数:4
相关论文
共 50 条
  • [1] One-pot synthesis of carbamates and thiocarbamates from Boc-protected amines
    Kim, Hee-Kwon
    Lee, Anna
    [J]. TETRAHEDRON LETTERS, 2016, 57 (44) : 4890 - 4892
  • [2] One-Pot Synthesis of Ureas from Boc-Protected Amines
    Spyropoulos, Constantinos
    Kokotos, Christoforos G.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (10): : 4477 - 4483
  • [3] Facile one-pot synthesis of unsymmetrical ureas, carbamates, and thiocarbamates from Cbz-protected amines
    Kim, Hee-Kwon
    Lee, Anna
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (30) : 7345 - 7353
  • [4] BF3-Catalyzed Synthesis of Cyclic Carbamates from Boc-Protected Aminals and Alkynes
    Kano, Taichi
    Yasumoto, Kento
    Maruoka, Keiji
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (08) : 1575 - 1578
  • [5] An efficient one-pot conversion of Boc-protected adenines to N6-ureas
    Machicao, Paulo A.
    Peterson, Matt A.
    Schols, Dominique
    [J]. TETRAHEDRON LETTERS, 2015, 56 (47) : 6574 - 6576
  • [6] Boc-protected amines via a mild and efficient one-pot Curtius rearrangement
    Lebel, H
    Leogane, O
    [J]. ORGANIC LETTERS, 2005, 7 (19) : 4107 - 4110
  • [7] Synthesis of α-alkyl-α-aminosilanes by rhodium-catalyzed hydrosilylation of Boc-protected vinyl amines
    Hewitt, GW
    Somers, JJ
    Sieburth, SM
    [J]. TETRAHEDRON LETTERS, 2000, 41 (52) : 10175 - 10179
  • [8] Synthesis of N -Trifluoromethyl Thiocarbamates and Ureas from 3-Aminopyridine-Derived Carbamates
    He, Xingjin
    Deng, Linbei
    You, Ying
    Lai, Yongxing
    Liu, Jianbo
    [J]. SYNTHESIS-STUTTGART, 2024, 56 (13): : 2118 - 2126
  • [9] Solid phase urea synthesis: An efficient and direct conversion of Fmoc-protected amines to ureas
    Chong, PY
    Petillo, PA
    [J]. TETRAHEDRON LETTERS, 1999, 40 (24) : 4501 - 4504
  • [10] Direct microwave synthesis of N,N′-diacylhydrazines and boc-protected hydrazides by in situ carbonylations under air
    Herrero, MA
    Wannberg, J
    Larhed, M
    [J]. SYNLETT, 2004, (13) : 2335 - 2338