Trimethyl Phosphite Mediated Simple Synthesis of Coumarins and Azacoumarins Through the Reaction of Phenols or Hydroxypyridines and Dimethyl Acetylenedicarboxylate (DMAD) or Diethyl Acetylenedicarboxylate (DEAD)

Protonation of the reactive intermediate produced in the reaction between trimethyl phosphite and dimethyl acetylenedicarboxylate or diethyl acetylenedicarboxylate by resorcinol, 5-methylresorcinol, 2,5-dihydroxyacetophenone, 4-chloro-2-methylphenol, 4-chloro-3,5-dimethy-lphenol, 4-hydroxypyridine,...

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Main Authors:	Shahram Moradi, Fatemeh Azarakhshi, Akbar Masoumi Shahi
Format:	Article
Language:	English
Published:	Iranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECR 2008-12-01
Series:	Iranian Journal of Chemistry & Chemical Engineering
Subjects:	2-oxo-2h-chromenes azacoumarins acetylenicester aromatic substitution trimethyl phosphate
Online Access:	http://www.ijcce.ac.ir/article_6936_cd9036b16a77cc53767a5929b3a780b7.pdf

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spelling	doaj-91590a5d17d34a9bbfb390623c87821c2020-11-25T01:29:00ZengIranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECRIranian Journal of Chemistry & Chemical Engineering 1021-99861021-99862008-12-0127435396936Trimethyl Phosphite Mediated Simple Synthesis of Coumarins and Azacoumarins Through the Reaction of Phenols or Hydroxypyridines and Dimethyl Acetylenedicarboxylate (DMAD) or Diethyl Acetylenedicarboxylate (DEAD)Shahram Moradi0Fatemeh Azarakhshi1Akbar Masoumi Shahi2Faculty of Chemistry, Islamic Azad University, Tehran North Branch, Tehran, I.R. IRANDepartment of Chemistry, Islamic Azad University, Arak Branch, Arak, I.R. IRANFaculty of Chemistry, Islamic Azad University, Tehran North Branch, Tehran, I.R. IRANProtonation of the reactive intermediate produced in the reaction between trimethyl phosphite and dimethyl acetylenedicarboxylate or diethyl acetylenedicarboxylate by resorcinol, 5-methylresorcinol, 2,5-dihydroxyacetophenone, 4-chloro-2-methylphenol, 4-chloro-3,5-dimethy-lphenol, 4-hydroxypyridine, 2-hydroxypyridine, 3-hydroxypyridine, or 8-hydroxyquinoline leads to vinylphosphonium salts, which undergo Michael addition with the conjugate base of the OH-acid to produce highly functionalized 2-oxo-2H-chromene or azacoumarins in good yields.http://www.ijcce.ac.ir/article_6936_cd9036b16a77cc53767a5929b3a780b7.pdf2-oxo-2h-chromenesazacoumarinsacetylenicesteraromatic substitutiontrimethyl phosphate
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Shahram Moradi Fatemeh Azarakhshi Akbar Masoumi Shahi
spellingShingle	Shahram Moradi Fatemeh Azarakhshi Akbar Masoumi Shahi Trimethyl Phosphite Mediated Simple Synthesis of Coumarins and Azacoumarins Through the Reaction of Phenols or Hydroxypyridines and Dimethyl Acetylenedicarboxylate (DMAD) or Diethyl Acetylenedicarboxylate (DEAD) Iranian Journal of Chemistry & Chemical Engineering 2-oxo-2h-chromenes azacoumarins acetylenicester aromatic substitution trimethyl phosphate
author_facet	Shahram Moradi Fatemeh Azarakhshi Akbar Masoumi Shahi
author_sort	Shahram Moradi
title	Trimethyl Phosphite Mediated Simple Synthesis of Coumarins and Azacoumarins Through the Reaction of Phenols or Hydroxypyridines and Dimethyl Acetylenedicarboxylate (DMAD) or Diethyl Acetylenedicarboxylate (DEAD)
title_short	Trimethyl Phosphite Mediated Simple Synthesis of Coumarins and Azacoumarins Through the Reaction of Phenols or Hydroxypyridines and Dimethyl Acetylenedicarboxylate (DMAD) or Diethyl Acetylenedicarboxylate (DEAD)
title_full	Trimethyl Phosphite Mediated Simple Synthesis of Coumarins and Azacoumarins Through the Reaction of Phenols or Hydroxypyridines and Dimethyl Acetylenedicarboxylate (DMAD) or Diethyl Acetylenedicarboxylate (DEAD)
title_fullStr	Trimethyl Phosphite Mediated Simple Synthesis of Coumarins and Azacoumarins Through the Reaction of Phenols or Hydroxypyridines and Dimethyl Acetylenedicarboxylate (DMAD) or Diethyl Acetylenedicarboxylate (DEAD)
title_full_unstemmed	Trimethyl Phosphite Mediated Simple Synthesis of Coumarins and Azacoumarins Through the Reaction of Phenols or Hydroxypyridines and Dimethyl Acetylenedicarboxylate (DMAD) or Diethyl Acetylenedicarboxylate (DEAD)
title_sort	trimethyl phosphite mediated simple synthesis of coumarins and azacoumarins through the reaction of phenols or hydroxypyridines and dimethyl acetylenedicarboxylate (dmad) or diethyl acetylenedicarboxylate (dead)
publisher	Iranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECR
series	Iranian Journal of Chemistry & Chemical Engineering
issn	1021-9986 1021-9986
publishDate	2008-12-01
description	Protonation of the reactive intermediate produced in the reaction between trimethyl phosphite and dimethyl acetylenedicarboxylate or diethyl acetylenedicarboxylate by resorcinol, 5-methylresorcinol, 2,5-dihydroxyacetophenone, 4-chloro-2-methylphenol, 4-chloro-3,5-dimethy-lphenol, 4-hydroxypyridine, 2-hydroxypyridine, 3-hydroxypyridine, or 8-hydroxyquinoline leads to vinylphosphonium salts, which undergo Michael addition with the conjugate base of the OH-acid to produce highly functionalized 2-oxo-2H-chromene or azacoumarins in good yields.
topic	2-oxo-2h-chromenes azacoumarins acetylenicester aromatic substitution trimethyl phosphate
url	http://www.ijcce.ac.ir/article_6936_cd9036b16a77cc53767a5929b3a780b7.pdf
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Trimethyl Phosphite Mediated Simple Synthesis of Coumarins and Azacoumarins Through the Reaction of Phenols or Hydroxypyridines and Dimethyl Acetylenedicarboxylate (DMAD) or Diethyl Acetylenedicarboxylate (DEAD)

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