Direct Synthesis of 1-Arylprop-1-ynes with Calcium Carbide as an Acetylene Source

被引:27
|
作者
Gao, Lei [1 ]
Li, Zheng [1 ]
机构
[1] Northwest Normal Univ, Coll Chem & Chem Engn, Lanzhou 730070, Gansu, Peoples R China
基金
中国国家自然科学基金;
关键词
arylpropynes; calcium carbide; tosylhydrazones; aralkynes; FRIEDEL-CRAFTS ALKENYLATION; ONE-POT SYNTHESIS; N-TOSYLHYDRAZONES; INTERNAL ALKYNES; STEREOSELECTIVE-SYNTHESIS; CATALYZED ALLYLATION; TERMINAL ALKYNES; FACILE SYNTHESIS; IONIC LIQUID; DERIVATIVES;
D O I
10.1055/s-0037-1610718
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple method is described for the synthesis of 1-arylprop-1-ynes directly from aromatic aldehyde p-tosylhydrazones by using calcium carbide as an acetylene source. The salient features of this protocol are its use of a readily available and easily handled source of acetylene, its operational simplicity, its high yield, and its broad substrate scope.
引用
收藏
页码:1580 / 1584
页数:5
相关论文
共 50 条
  • [31] Direct Synthesis of Propen-2-yl Sulfones through Cascade Reactions Using Calcium Carbide as an Alkyne Source
    Gao, Lei
    Liu, Zhenrong
    Ma, Xiaolong
    Li, Zheng
    ORGANIC LETTERS, 2020, 22 (13) : 5246 - 5250
  • [32] On the oxidative addition of 1-halogenalk-1-ynes - Synthesis and structure of phenylalkynylalladium complexes
    Weigelt, M
    Becher, D
    Poetsch, E
    Bruhn, C
    Steinborn, D
    ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1999, 625 (09): : 1542 - 1547
  • [33] ACETYLENE REACTIONS .2. OXIDATION, HYDRATION, AND MANNICH REACTIONS WITH 3-AMINOBUT-1-YNES
    ROSE, JD
    WEEDON, BCL
    JOURNAL OF THE CHEMICAL SOCIETY, 1949, (APR): : 782 - 785
  • [34] Calcium Carbide as a Surrogate of Acetylene: Copper-Catalyzed Construction of 3-Methylene-2-arylisoindolin-1-ones
    Liu, Haiyan
    You, Xinjie
    Wen, Fei
    Zhang, Zeshuai
    Li, Zheng
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (07)
  • [35] Synthesis of Enantiopure 1-Arylprop-2-en-1-ols and Their tert-Butyl Carbonates
    Stambasky, Jan
    Malkov, Andrei V.
    Kocovsky, Pavel
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22): : 9148 - 9150
  • [36] Calcium carbide as the acetylide source: transition-metal-free synthesis of substituted pyrazoles via [1,5]-sigmatropic rearrangements
    Yu, Yue
    Huang, Wei
    Chen, Yang
    Gao, Bingjie
    Wu, Wanqing
    Jiang, Huanfeng
    GREEN CHEMISTRY, 2016, 18 (24) : 6445 - 6449
  • [37] SYNTHESIS OF 3 PHENOLIC PENT-1-EN-4-YNES
    DREWES, SE
    EMSLIE, ND
    HEMINGWAY, M
    SYNTHETIC COMMUNICATIONS, 1990, 20 (11) : 1671 - 1679
  • [38] A concise synthesis of rooperol and related 1,5-diarylpent-1-en-4-ynes
    Kerwin, Sean M.
    Cha, Jonathan
    TETRAHEDRON LETTERS, 2014, 55 (01) : 137 - 141
  • [39] Construction of pyrazolo[1,5-a]pyrimidines and pyrimido[1,2-b]indazoles with calcium carbide as an alkyne source
    You, Xinjie
    Wang, Botao
    Wen, Fei
    Li, Zheng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (28) : 5822 - 5826
  • [40] Direct Synthesis of Symmetric Diarylethynes from Calcium Carbide and Arylboronic Acids/Esters
    Fu, Rugang
    Li, Zheng
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (45) : 6648 - 6651