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

来源：

SYNLETT | 2019年 / 30卷 / 13期

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

页码：1580 / 1584

页数：5

共 50 条

[21] SYNTHESIS AND ELECTRONIC SPECTRA OF 1,1'-DIANTHRYLPOLY-YNES
AKIYAMA, S
NAKAGAWA, M
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1967, 40 (02) : 340 - +
[22] Synthesis of (1E)-1-Chloroalk-1-en-4-ynes
Shakhmaev, R. N.
Ignatishina, M. G.
Zorin, V. V.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2020, 90 (07) : 1365 - 1367
[23] Synthesis of (1E)-1-Chloroalk-1-en-4-ynes
R. N. Shakhmaev
M. G. Ignatishina
V. V. Zorin
Russian Journal of General Chemistry, 2020, 90 : 1365 - 1367
[24] Facile One-Pot Synthesis of Monosubstituted 1-Aryl-1H-1,2,3-triazoles from Arylboronic Acids and Prop-2-ynoic Acid (=Propiolic Acid) or Calcium Acetylide (=Calcium Carbide) as Acetylene Source
Yang, Qing
Jiang, Yubo
Kuang, Chunxiang
HELVETICA CHIMICA ACTA, 2012, 95 (03) : 448 - 454
[25] Click Reaction of Calcium Carbide-Derived Acetylene as a Direct Way to Chromophore- and Fluorophore-Substituted 1,2,3-Triazoles
Voronin, V. V.
Ledovskaya, M. S.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2024, 94 (12) : 3149 - 3154
[26] SYNTHESIS OF 4-DIALKYLAMINO-1-ACYL-1-BUTEN-3-YNES
OSTROUMOV, IG
KHAKUNOVA, EY
TSILKO, AE
MARETINA, IA
PETROV, AA
ZHURNAL ORGANICHESKOI KHIMII, 1990, 26 (12): : 2508 - 2510
[27] Calcium Carbide as Acetylene Source in Cascade Assemblies of Hydroxypyrrolines and 3H-Pyrroles from Ketoximes
Shabalin, Dmitrii A.
Dubovtsev, Alexey Yu.
Schmidt, Elena Yu.
Trofimov, Boris A.
CHEMISTRYSELECT, 2020, 5 (11): : 3434 - 3437
[28] The Use of Calcium Carbide as Acetylene Source in a Three-Component Coupling with ω-Chlorinated Ketones and Primary Amines
Van Beek, Wim E.
Gadde, Karthik
Tehrani, Kourosch Abbaspour
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (62) : 16645 - 16651
[29] OBSERVATION ON THE SYNTHESIS OF ALLENES BY HOMOLOGATION OF ALK-1-YNES
SEARLES, S
LI, Y
NASSIM, B
LOPES, MTR
TRAN, PT
CRABBE, P
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (04): : 747 - 751
[30] Synthesis of 2-ynamides by direct palladium-catalyzed oxidative aminocarbonylation of alk-1-ynes
Gabriele, B
Salerno, G
Veltri, L
Costa, M
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 622 (1-2) : 84 - 88

← 1 2 3 4 5 →