19th Iranian Seminar on Organic Chemistry , 2012-09-05

Title : ( One-Pot Synthesis of Stable Phosphorus Ylides by Three Component Reaction between Electron-Deficient Acetylenic Esters, Triphenylphosphine and Thione Groups )

Authors: Hossein Eshghi , Mehdi Bakavoli , javad abedini torghabeh , Mohammad Rahimizadeh , Amir Keykha ,

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Electron-deficient acetylenic esters have proven to be very versatile reagent for the preparation of stable phosphorus ylides and many different products containing heterocycles can be synthesized [1,2]. Indeed, several series of heterocyclic compounds possessing a bridgehead thiazole or thiazine moiety play a vital role in many biological activities [3]. The present study aims to test the reactivity of DMAD towards imidazolidine-2-thione, pyrimidine-2-thione and N-phenylthiourea in the presence of triphenylphosphine. The new stable phosphorus ylides have been prepared in excellent yields by the three-components approach starting with activated electron-deficient acetylenic esters (dimethyl and diethyl acetylenedicarboxylate (DMAD and DEAD)), and imidazolidine-2-thione or pyrimidine-2-thione or N-phenylthiourea in the presence of triphenylphosphine. In some cases these ylides were cyclized to dihydro pyrimido thiazine, thioxoimidazolidine and thioxo tetrahydro pyrimidine derivatives. The FT-IR, 1H-NMR, 13C-NMR spectra confirm the structure of compounds.

Keywords

, phosphorus ylides, thiazole or
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@inproceedings{paperid:1029516,
author = {Eshghi, Hossein and Bakavoli, Mehdi and Abedini Torghabeh, Javad and Rahimizadeh, Mohammad and Keykha, Amir},
title = {One-Pot Synthesis of Stable Phosphorus Ylides by Three Component Reaction between Electron-Deficient Acetylenic Esters, Triphenylphosphine and Thione Groups},
booktitle = {19th Iranian Seminar on Organic Chemistry},
year = {2012},
location = {رفسنجان, IRAN},
keywords = {phosphorus ylides; thiazole or thiazine},
}

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%0 Conference Proceedings
%T One-Pot Synthesis of Stable Phosphorus Ylides by Three Component Reaction between Electron-Deficient Acetylenic Esters, Triphenylphosphine and Thione Groups
%A Eshghi, Hossein
%A Bakavoli, Mehdi
%A Abedini Torghabeh, Javad
%A Rahimizadeh, Mohammad
%A Keykha, Amir
%J 19th Iranian Seminar on Organic Chemistry
%D 2012

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