Methyl Pyruvate Oxime as a Carbonyl Synthon: Synthesis of Ureas, Carbamates, Thiocarbamates, and Anilides

被引:0
|
作者
Kim, Seo Yeon [1 ]
Lim, Hee Nam [1 ]
机构
[1] Yeungnam Univ, Dept Chem, Gyongsan 38541, Gyeongbuk, South Korea
基金
新加坡国家研究基金会;
关键词
CATALYZED CARBONYLATION; UNSYMMETRICAL UREAS; PRACTICAL SYNTHESIS; AMINES; ACIDS; MILD; CO2;
D O I
10.1021/acs.orglett.4c01007
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new strategy for the synthesis of unsymmetrical ureas, carbamates, thiocarbamates, and anilides was developed with methyl pyruvate oxime as the carbonyl synthon. The intrinsic reactivity of the reagent enabled consecutive disubstitution involving direct amidation and one-pot deoximative substitution with various nucleophiles. The utility of the method was demonstrated with the synthesis of bioactive molecules.
引用
收藏
页码:3850 / 3854
页数:5
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共 23 条
  • [1] Carbamoylimidazolium and thiocarbamoylimidazolium salts: novel reagents for the synthesis of ureas, thioureas, carbamates, thiocarbamates and amides
    Grzyb, JA
    Shen, M
    Yoshina-Ishii, C
    Chi, W
    Brown, RS
    Batey, RA
    [J]. TETRAHEDRON, 2005, 61 (30) : 7153 - 7175
  • [2] 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
  • [3] Direct synthesis of carbamates, thiocarbamates, and ureas from Boc-protected amines: a sustainable and efficient approach
    Li, Wanyong
    Lv, Mengting
    Luo, Xiaolin
    Wang, Zhouyu
    Song, Qiao
    Yu, Xiaoqi
    [J]. RSC ADVANCES, 2024, 14 (29) : 20656 - 20659
  • [4] 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
  • [5] Intra- and intermolecular hydrogen bonding in N,N '-Carbonyl bis (carbamates),-( S-thiocarbamates) and N,N '-biscarbamoyl ureas
    Pfeiffer, Jonathan
    Mobs, Martin
    Reith, Sascha
    Tallu, Mirko
    Tambornino, Frank
    [J]. JOURNAL OF MOLECULAR STRUCTURE, 2024, 1309
  • [6] N-Alkyl Carbamoylimidazoles as Isocyanate Equivalents: Exploration of the Reaction Scope for the Synthesis of Ureas, Hydantoins, Carbamates, Thiocarbamates, and Oxazolidinones
    Bansagi, Jazmin
    Wilson-Konderka, Cody
    Debrauwer, Vincent
    Narayanan, Pournima
    Batey, Robert A.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (17): : 11329 - 11349
  • [7] USE OF METHYL THIOMETHYL SULFOXIDE AS CARBONYL SYNTHON FOR SYNTHESIS OF DIALKYL KETONES
    SCHILL, G
    JONES, PR
    [J]. SYNTHESIS-STUTTGART, 1974, (02): : 117 - 118
  • [8] Achieving functional group diversity in parallel synthesis: solution-phase synthesis of a library of ureas, carbamates, thiocarbamates, and amides using carbamoylimidazolium salts
    Grzyb, Justyna A.
    Batey, Robert A.
    [J]. TETRAHEDRON LETTERS, 2008, 49 (36) : 5279 - 5282
  • [9] Green and efficient synthesis of thioureas, ureas, primary O-thiocarbamates, and carbamates in deep eutectic solvent/catalyst systems using thiourea and urea
    Bagherzadeh, Nastaran
    Sardarian, Ali Reza
    Inaloo, Iman Dindarloo
    [J]. NEW JOURNAL OF CHEMISTRY, 2021, 45 (26) : 11852 - 11858
  • [10] SYNTHESIS AND ANTHELMINTIC ACTIVITY OF SOME CARBAMATES, THIOCARBAMATES AND UREAS DERIVED FROM 6-CARBOXY-5(H)-OXOTHIAZOLO[3,2-A]PYRIMIDINE
    SHRIDHAR, DR
    JOGIBHUKTA, M
    KRISHNAN, VSH
    [J]. INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1986, 25 (03): : 345 - 346