SYNTHESIS OF STABILIZED PHOSPHORUS YLIDES FROM ELECTRON-POOR ALCOHOLS AND THEIR APPLICATIONS IN THE PREPARATION OF 2,5-DIHYDROFURAN DERIVATIVES

被引：4

作者：

Salmanpour, Sadegh ^{[2
]}

Ramazani, Ali ^{[1
]}

Ahmadi, Yavar ^{[3
]}

机构：

[1] Islamic Azad Univ, Dept Chem, Zanjan Branch, Zanjan, Iran

[2] Islamic Azad Univ, Sari Branch, Dept Chem, Sari, Iran

[3] Zanjan Univ, Dept Chem, Zanjan, Iran

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF ETHIOPIA | 2012年 / 26卷 / 01期

关键词：

Electron-poor alcohol; Acetylenic esters; Ninhydrin; Intramolecular Wittig reaction; Vinyltriphenylphosphonium salt; ONE-POT SYNTHESIS; CATALYZED STEREOSELECTIVE CONVERSION; AROMATIC CARBOXYLIC-ACIDS; SINGLE-CRYSTAL STRUCTURE; X-RAY-STRUCTURE; 3-COMPONENT REACTION; SILICA-GEL; 1,3,4-OXADIAZOLE DERIVATIVES; 4-COMPONENT SYNTHESIS; SECONDARY AMINE;

D O I：

10.4314/bcse.v26i1.18

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by alcohols (2-methanol thiophen, 3-methanol thiophen, 1,1,1,3,3,3-hexafluoro-2-propanol and [4-(trifluoromethyl)-phenyl] methanol) leads to vinyltriphenylphosphonium salts, which undergo Michael addition reaction with conjugate base to produce the corresponding stabilized phosphorus ylides. Wittig reaction of the stabilized phosphorus ylides with ninhydrin leads to the corresponding densely functionalized 2H-indeno[2,1-b]furans in fairly good yields.

引用

页码：153 / 158

页数：6

共 48 条

[1] Synthesis of electron-poor pyrazole derivatives from in-situ generated stabilized phosphorus ylides
Ganjeie, Bijan
Ramazani, Ali
Kazemizadeh, Ali Reza
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2007, 182 (08) : 1703 - 1708
[2] Synthesis of 2,3,4-trisubstituted 2,5-dihydrofuran derivatives
Gowrisankar, S
Park, DY
Kim, JN
[J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2005, 26 (11): : 1826 - 1828
[3] DERIVATIVES OF FURAN AND 2,5-DIHYDROFURAN FROM CUMULENIC CARBINOL ETHERS
ROMPES, JA
HOFF, S
MONTIJN, PP
BRANDSMA, L
ARENS, JF
[J]. RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS, 1969, 88 (12): : 1445 - &
[4] Synthesis of highly electron-poor alkenes from in situ generated stabilized phosphorus ylides and ninhydrin via intermolecular Wittig reaction
Ramazani, A
Bodaghi, A
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2004, 179 (08) : 1615 - 1620
[5] Stereoselective Synthesis of Conjugated Bisallenols as Precursors of Novel Bis(2,5-dihydrofuran) Derivatives
Poonoth, Manojkumar
Krause, Norbert
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (1-2) : 117 - 122
[6] Synthesis of 2,5-dihydrofuran and tetrahydrofuran from 1,3-butadiene
Bobyleva, LI
Abreimova, MA
Rybina, GV
Kryukov, SI
Moskvichev, YA
[J]. PETROLEUM CHEMISTRY, 2004, 44 (03) : 188 - 192
[7] Isosarcophytoxide Derivatives with a 2,5-Dihydrofuran Moiety from the Soft Coral Sarcophyton cinereum
Chao, Chih-Hua
Wu, Yuan-Jhong
Huang, Tzu-Yin
Tai, Chi-Jen
Chen, Yi-Ju
Huang, Chiung-Yao
Lin, Chi-Chien
Dai, Chang-Feng
Huang, Hui-Chi
Sheu, Jyh-Horng
[J]. MOLECULES, 2023, 28 (02):
[8] Focused microwave-assisted synthesis of 2,5-dihydrofuran derivatives as electron acceptors for highly efficient nonlinear optical chromophores
Liu, S
Haller, MA
Ma, H
Dalton, LR
Jang, SH
Jen, AKY
[J]. ADVANCED MATERIALS, 2003, 15 (7-8) : 603 - 607
[9] Focused microwave-assisted synthesis of 2,5-dihydrofuran derivatives as electron acceptors for highly efficient nonlinear optical chromophores
Liu, S
Haller, MA
Luo, JD
Jang, SH
Ma, H
Dalton, LR
Jen, AKY
[J]. ORGANIC AND POLYMERIC MATERIALS AND DEVICES, 2003, 771 : 375 - 380
[10] Efficient and mild synthesis of highly substituted 2,5-dihydrofuran and furan derivatives via stepwise reaction
Wang, Tiantian
Liu, Jia
Lv, Zhiliang
Zhong, Hanyu
Chen, Huan
Niu, Chunjuan
Li, Ke
[J]. TETRAHEDRON, 2011, 67 (19) : 3476 - 3482

← 1 2 3 4 5 →