scholarly journals Three-Component Reaction of Triphenylphosphine, Acetylenic Esters and 4-(Arylideneamino)-3-ethyl-1H-1,2,4-triazole-5(4H)-thiones for the Synthesis of Phosphorus Ylides

2011 ◽  
Vol 8 (s1) ◽  
pp. S27-S32
Author(s):  
Mohammad H. Mosslemin ◽  
Masoumeh Tabatabaee ◽  
Alireza Hassanabadi ◽  
Asal Lamei
Keyword(s):  
Phosphorus Ylides ◽  
Acetylenic Esters ◽  
Dialkyl Acetylenedicarboxylates ◽  
Three Component Reaction

Triphenylphosphine reacts with ‎4-(arylideneamino)-3-ethyl-1H-1,2,4-triazole-5(4H)-thiones in the presence of dialkyl acetylenedicarboxylates to produce highly functionalized, salt-free phosphorus ylides in excellent yields.

Synthesis and Variable Temperature 1H and 31P NMR Study of Phosphorus Ylides derived from reaction of NH-acids, triarylphosphine and acetylenic esters

2007 ◽  
Vol 2007 (6) ◽  
pp. 353-355 ◽  
Author(s):  
Seyyed Javad Sabounchei ◽  
Hassan Nemattalab
Keyword(s):  
Mass Spectroscopy ◽  
Nmr Spectra ◽  
31P Nmr ◽  
Variable Temperature ◽  
Phosphorus Ylides ◽  
Acetylenic Esters ◽  
Dialkyl Acetylenedicarboxylates ◽  
Nmr Study ◽  
One Step ◽  
C Nmr

A one-step synthesis of sterically congested phosphorus ylides in moderate to good yields by the reaction of dialkyl acetylenedicarboxylates, NH-acids and triarylphosphines are reported. Characterisation of the obtained compounds was performed by IR, 1H, 31P, 13C NMR, elemental analysis and mass spectroscopy. NMR spectra showed that some of these compounds (in CDCl3 as solvent) contained two rotamers with unequal populations that equilibrate rapidly at higher temperatures.

Three-Component Reaction of Triphenylphosphine, Acetylenic Esters, and Arylsulfonyl Hydrazides or Aryl Hydrazines: An Efficient One-Pot Synthesis of Stable β-Nitrogen-Substituted Phosphorus Ylides

2008 ◽  
Vol 38 (12) ◽  
pp. 1990-1999 ◽  
Author(s):  
Hossein Anaraki-Ardakani ◽  
Shirin Sadeghian ◽  
Foroghossadat Rastegari ◽  
Alireza Hassanabadi ◽  
Mohammad Anary-Abbasinejad
Keyword(s):  
Phosphorus Ylides ◽  
Acetylenic Esters ◽  
One Pot ◽  
One Pot Synthesis ◽  
Three Component Reaction

Water–acetone Media Enforced Chemoselective Synthesis of 2-substituted Pyrrole Stable Phosphorus Ylides from Reaction between Pyrrole and Acetylenic Esters in the Presence of Triphenylphosphine

2007 ◽  
Vol 2007 (10) ◽  
pp. 566-568 ◽  
Author(s):  
Malek Taher Maghsoodlou ◽  
Nourollah Hazeri ◽  
Sayyed Mostafa Habibi-Khorassani ◽  
Zohreh Moeeni ◽  
Ghasem Marandi ◽  
...  
Keyword(s):  
Good Yield ◽  
Phosphorus Ylides ◽  
Acetylenic Esters ◽  
Dialkyl Acetylenedicarboxylates ◽  
Chemoselective Synthesis ◽  
Stable Phosphorus Ylides

Pyrrole undergoes a smooth reaction with dialkyl acetylenedicarboxylates in the presence of triphenylphosphine in a mixture of water–acetone (50:50) as a solvent pathway to produce phosphorus ylides of 2-substituted pyrrole in good yield.

Three-component reaction between Triphenylphosphine, Acetylenic Esters and 4-hydroxycoumarin, 4-(phenylamino)coumarin, 4-hydroxyquinolin-2(1H)-one or 4-hydroxy-1-methylquinolin-2(1H)-one

2007 ◽  
Vol 2007 (10) ◽  
pp. 605-608 ◽  
Author(s):  
Mohammad Anary-Abbasinejad ◽  
Hossein Anaraki-Ardakani ◽  
Ali Ezadi ◽  
Alireza Hassanabadi
Keyword(s):  
Acetylenic Esters ◽  
Dialkyl Acetylenedicarboxylates ◽  
Three Component Reaction

Three-component reaction between dialkyl acetylenedicarboxylates and triphenylphosphine in the presence of 4-hydroxycoumarin, 4-(phenylamino)coumarin, 4-hydroxyquinolin-2(1 H)-one or 4-hydroxy-1-methylquinolin-2(1 H)-one is described.

ChemInform Abstract: Three-Component Reaction Between Alkyl(aryl) Isocyanides and Dialkyl Acetylenedicarboxylates in the Presence of Ethyl Trifluoroacetate.

ChemInform ◽  
2011 ◽  
Vol 42 (40) ◽  
pp. no-no
Author(s):  
Khatereh Khandan-Barani ◽  
Malek Taher Maghsoodlou ◽  
Sayyed Mostafa Habibi-Khorasani ◽  
Nourallah Hazeri ◽  
Seyyed Sajad Sajadikhah
Keyword(s):  
Alkyl Aryl ◽  
Dialkyl Acetylenedicarboxylates ◽  
Three Component Reaction

Nucleophilic Phosphine-Promoted Domino Reaction of Dialkyl Acetylenedicarboxylates and 3-Arylamino-1-methyl-1H-pyrrole-2,5-diones

Synthesis ◽  
2018 ◽  
Vol 50 (18) ◽  
pp. 3715-3722 ◽  
Author(s):  
Ying Han ◽  
Chao-Guo Yan ◽  
Chang-Zhou Liu ◽  
Yuan-Yuan Zhang ◽  
Jing Sun
Keyword(s):  
Room Temperature ◽  
Domino Reaction ◽  
Dimethyl Acetylenedicarboxylate ◽  
Dialkyl Acetylenedicarboxylates ◽  
Three Component Reaction

The three-component reaction of triphenylphosphine, dimethyl acetylenedicarboxylate and 3-arylamino-1-methyl-1H-pyrrole-2,5-diones in CH2Cl2 at room temperature resulted in functionalized 3-(triphenyl-λ5-phosphanylidene)succinates in nearly quantitative yields. However, tri(n-butyl)phosphine promoted reaction of dialkyl acetylenedicarboxylates and 3-arylamino-1-methyl-1H-pyrrole-2,5-diones in CH2Cl2 afforded functionalized pyrrolo[3,4-b]pyridine-4-carboxylates in satisfactory yields.

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