Dipotassium hydrogen phosphate powder catalyzed conversion of dialkyl 2-(2,5-dihydroxyphenyl)-3-(1,1,1-triphenyl-λ5-phosphanylidene)succinates to alkyl 6-hydroxy-2-oxo-2H-chromen-4-carboxylates

被引：19

作者：

Souldozi, A ^{[1
]}

Ramazani, A ^{[1
]}

Noshiranzadeh, N ^{[1
]}

机构：

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

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2006年 / 181卷 / 03期

关键词：

dipotassium hydrogen phosphate; hydroquinone; acetylenic ester; triphenylphosphine; vinyltriphenylphosphonium salt;

D O I：

10.1080/10426500500269570

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by hydroquinone leads to vinyltriphenylphosphonium salts, which undergo an electrophilic substitution reaction with a conjugate base to produce corresponding stabilized phosphorus ylides. Dipotassium hydrogen phosphate powder was found to catalyze conversion of the stabilized phosphorus ylides to alkyl 6-hydroxy-2-oxo-2H-chromene-4-carboxylates under thermal or microwave irradiation in solvent-free conditions.

引用

页码：587 / 589

页数：3

共 50 条

[1] Silica gel catalyzed conversion of dialkyl 2-(2-hydroxy-1-naphthyl)-3-(1,1,1-triphenyl-λ5-phosphanylidene) succinates to alkyl 3-oxo-3H-benzo[f]chromene-1-carboxylates in solvent-free conditions
Ramazani, A
Souldozi, A
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2003, 178 (06) : 1329 - 1332
[2] Synthesis of dialkyl 2-(1-cyano-2-oxo-1-phenyl-alkyl)-3-(triphenyl-λ5-phosphanylidene)-succinates
Yavari, I
Islami, MR
Habibi, A
Tikdari, AM
Ebrahimi, L
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2004, 179 (03) : 575 - 583
[3] Synthesis of dialkyl 2-(2-oxo-2-phenylethyl)-3-(1,1,1-triphenyl-λ5-phosphanylidene)succinates from triphenylphosphine, acetylenic ester and 4,4,4-trifluoro-1-phenyl-1,3-butanedione in the presence of basic alumina powder
Jafari, Ali
Ahmadi, Ebrahim
Alinia, Mokhtar
Ramazani, Ali
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (05) : 1116 - 1123
[4] One-pot synthesis of dimethyl 2-[acyl(1-naphthyl)amino]-3-(1,1, 1-triphenyl-λ5-phosphanylidene)succinates
Ramazani, A
Karimi-Avargani, L
Gouranlou, F
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2003, 42 (02): : 390 - 392
[5] Synthesis of alkyl 2-(2-oxo-1,2-dihydronaphtho[2,1-b]thiophen-1-yl)-2-(1,1,1-triphenyl-λ5-phosphanylidene)acetates from triphenylphosphine, acetylenic esters, and 2-naphthalenethiol
Amini, Issa
Ramazani, Ali
Ahankar, Hamideh
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (08) : 1994 - 1999
[6] Silica gel catalyzed conversion of dialkyl 2-(1-hydroxy-2-naphthyl)-3-(triphenylphosphoranylidene)-butanedioates to alkyl 2-oxo-2H-benzo[h]chromene-4-carboxylates in solvent-free conditions
Ramazani, A
Souldozi, A
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2003, 178 (06) : 1325 - 1328
[7] Dipotassium hydrogen phosphate powder catalyzed conversion of dimethyl-2-(5-bromo-2-hydroxyphenyl)-3-(triphenylphosphoranylidene)butanedioate to methyl-6-bromo-2-oxo-2H-chromene-4-carboxylate
Ramazani, Ali
Yousefi, Leila
Souldozi, Ali
Noshiranzadeh, Nader
ASIAN JOURNAL OF CHEMISTRY, 2007, 19 (02) : 1595 - 1596
[8] Silica gel catalyzed stereoselective conversion of dialkyl 2-(3-acetyl-4-hydroxy-1-naphthyl)-3-(triphenylphosphoranylidene) butanedioates to dialkyl 2-(3-acetyl-4-hydroxy-1-naphthyl)-2-butenedioates in solvent-free conditions
Ramazani, A
Momeni-Movahhed, A
Gouranlou, F
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2002, 177 (04) : 903 - 907
[9] SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF 2-ACETYL-5-HYDROXY-5-METHYL-3-PHENYL-1-CYCLOHEXANONE AND ALKYL-4-HYDROXY-4-METHYL-2-OXO-6-PHENYLCYCLOHEXANE-1-CARBOXYLATES
Gein, V. L.
Vagapov, A. V.
Nosova, N. V.
Voronina, E. V.
Vakhrin, M. I.
Kriven'ko, A. P.
PHARMACEUTICAL CHEMISTRY JOURNAL, 2010, 44 (05) : 245 - 247
[10] Synthesis and antimicrobial activity of 2-acetyl-5-hydroxy-5-methyl-3-phenyl-1cyclohexanone and alkyl-4-hydroxy-4-methyl2-oxo-6-phenylcyclohexane-1-carboxylates
V. L. Gein
A. V. Vagapov
N. V. Nosova
E. V. Voronina
M. I. Vakhrin
A. P. Kriven’ko
Pharmaceutical Chemistry Journal, 2010, 44 : 245 - 247

← 1 2 3 4 5 →