Study of Reaction between Activated Acetylenes and N,N′-Diethyl-2-thiobarbituric Acid in the Presence of Isocyanides or Triphenylphosphine

被引：18

作者：

Marandi, Ghasem ^{[2
]}

Maghsoodlou, Malek Taher ^{[1
]}

Hazeri, Nourallah ^{[1
]}

Heydari, Reza ^{[1
]}

Khorassani, Sayyed Mostafa Habibi ^{[1
]}

Ebrahimi, Ali ^{[1
]}

Poor, Sakineh Mollaee ^{[1
]}

Mandiabad, Hassan Hosseini ^{[1
]}

Nassiri, Mahmoud ^{[1
]}

Kabiri, Roya ^{[3
]}

机构：

[1] Univ Sistan & Baluchestan, Dept Chem, Zahedan, Iran

[2] Payame Noor Univ Khoy, Fac Sci, Dept Chem, Khoy, Iran

[3] Univ Tabriz, Fac Chem, Tabriz, Iran

来源：

HETEROATOM CHEMISTRY | 2010年 / 21卷 / 04期

关键词：

STABLE PHOSPHORUS YLIDES; PHOSPHINE-CATALYZED REACTION; ONE-POT SYNTHESIS; FACILE SYNTHESIS; ROUTE;

D O I：

10.1002/hc.20601

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In a series of separate experiments reaction between N,N'-diethyl-2-thiobarbituric acid and acetylenic diesters in the presence of isocyanides or triphenylphosphine led to highly functionalized 4H-pyrano[2,3-d]thiopyrimidine or 1,4-di-ionic organophosphorus derivatives. The H-1 NMR spectra of diethyl-7-(2,6-dimethylphenylamino)-4-oxo-2-thio-1,3-diethyl-4H-pyrano[2,3-d]pyrimidine-5,6-dicarboxylate showed dynamic NMR effect that was attributed to restricted rotation around the aryl-nitrogen single bond. Activation free energy (Delta G(not equal)) for this process is about 54.85 +/- 2 kJ mol(-1) Betaines as 1,4-diionic organophosphorus compounds in this reaction are possessed of two vicinal stereo genic centers and exist in the solution as a mixture of two diastereoisomers. (C) 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:228-235, 2010; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20601

引用

页码：228 / 235

页数：8

共 50 条

[21] Novel synthesis of stable 1,5-diionic organophosphorus compounds from the reaction between triphenylphosphine and acetylenedicarboxylic acid in the presence of N–H heterocyclic compounds
Morteza Ziyaadini
Malek Taher Maghsoodlou
Nourallah Hazeri
Sayyed Mostafa Habibi-Khorassani
Monatshefte für Chemie - Chemical Monthly, 2012, 143 : 1681 - 1685
[22] Reaction between alkyl isocyanides and dimethyl acetylenedicarboxylate in presence of N,N′-dimethylbarbituric acid.: A convenient route to highly functionalized 4H-pyrano[3,2-d]pyrimidine derivatives
Yavari, I
Maghsoodlou, MT
JOURNAL OF CHEMICAL RESEARCH-S, 1998, (07): : 386 - +
[23] Unexpected formation of hydroxyborazaphosphonic acid in the reaction of (N-benzyl)benzylideneimine-2-boronic acid with diethyl phosphite
Rydzewska, Agata
Slepokura, Katarzyna
Lis, Tadeusz
Kafarski, Pawel
Mlynarz, Piotr
TETRAHEDRON LETTERS, 2009, 50 (01) : 132 - 134
[24] REACTION OF N-1,2,2,2-TETRACHLOROETHYLAMIDES OF ACIDS WITH DIPHENYLPHOSPHINOUS ACID ETHYL-ESTER AND TRIPHENYLPHOSPHINE
DRACH, BS
SVIRIDOV, EP
KIRSANOV, AV
ZHURNAL OBSHCHEI KHIMII, 1975, 45 (01): : 12 - 16
[25] Novel synthesis of stable 1,5-diionic organophosphorus compounds from the reaction between triphenylphosphine and acetylenedicarboxylic acid in the presence of N-H heterocyclic compounds
Ziyaadini, Morteza
Maghsoodlou, Malek Taher
Hazeri, Nourallah
Habibi-Khorassani, Sayyed Mostafa
MONATSHEFTE FUR CHEMIE, 2012, 143 (12): : 1681 - 1685
[26] CALORIMETRIC STUDY OF THE REACTION BETWEEN FORMIC-ACID AND N,N,N',N'-TETRAMETHYLETHYLENEDIAMINE FROM THE ASPECT OF THERMAL-ENERGY STORAGE
SALMAN, M
GIRAULT, Y
BALBI, N
ELEGANT, L
JOURNAL OF THERMAL ANALYSIS, 1991, 37 (10): : 2389 - 2394
[27] Three-component reaction between ethyl N-(4-oxo-2-thioxothiazolidin-3-yl)oxalamate and acetylenic esters in the presence of triphenylphosphine
Hassanabadi, Alireza
JOURNAL OF CHEMICAL RESEARCH, 2013, (03) : 149 - 151
[28] SPECTROPHOTOMETRIC STUDY OF REACTION BETWEEN PICRIC ACID AND N,N'-DIPHENYLGUANIDINE IN CARBOXYLIC-ACIDS AND IN BENZENE MEDIA
KOKOT, Z
JASINSKI, T
ROCZNIKI CHEMII, 1972, 46 (7-8): : 1335 - &
[29] Colour reaction of chromium (VI) with N,N-diethyl-1,4-phenylenediamine in the presence of ethanol and cyclohexyldiamine tetraacetic acid as well as its application in the species analysis of chromium
Zhang, MH
Zhang, QR
Fang, Z
Lei, ZC
TALANTA, 1999, 48 (02) : 369 - 375
[30] Reaction between acid N'-(2-oxo-2-phenyl-ethyl)hydrazides, acetylenic esters and alkyl isocyanides in the presence of silica sulfuric acid: One-pot synthesis of highly functionalized 2,3-dihydro-1H-pyrazoles
Ardakani, Leili Shaker
Mosslemin, Mohammad H.
Hassanabadi, Alireza
Hashemian, Saeedeh
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2021, 196 (11) : 1004 - 1009

← 1 2 3 4 5 →