Synthesis of Pyrrole Phosphonate Esters: Emphasis on Pyrrole NH Acids and Dialkylacetylenic Esters Substitution

M.T. Maghsoodlou; R.C. Faramarz; H.K. Sayed Mostafa; K. Maryam; Mohamed Makha

Synthesis of Pyrrole Phosphonate Esters: Emphasis on Pyrrole NH Acids and Dialkylacetylenic Esters Substitution

M.T. Maghsoodlou, R.C. Faramarz, H.K. Sayed Mostafa, K. Maryam, Mohamed Makha

School of Molecular Sciences

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

Reaction of dialkyl acetylenedicarboxylates 1a-c and pyrrole derivatives 2a-e in thepresence of triphenylphosphite (TPP) was investigated and the effect of the pyrrole substitution wasestablished. Diastereoselectivity is observed with pyrroles, 2a,b, yielding phosphonate esterderivatives 3a-f and 4, and their relative configuration is determined by 1H/13C and 31P NMR andconfirmed by single X-ray diffraction. Similar reactions with higher degree of substitution of thepyrrole, 2c,e showed no diastereoselectivity.

Original language	English
Pages (from-to)	105-113
Journal	Iranian Journal of Chemistry and Chemical Engineering
Volume	27
Issue number	1
Publication status	Published - 2008

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title = "Synthesis of Pyrrole Phosphonate Esters: Emphasis on Pyrrole NH Acids and Dialkylacetylenic Esters Substitution",

abstract = "Reaction of dialkyl acetylenedicarboxylates 1a-c and pyrrole derivatives 2a-e in thepresence of triphenylphosphite (TPP) was investigated and the effect of the pyrrole substitution wasestablished. Diastereoselectivity is observed with pyrroles, 2a,b, yielding phosphonate esterderivatives 3a-f and 4, and their relative configuration is determined by 1H/13C and 31P NMR andconfirmed by single X-ray diffraction. Similar reactions with higher degree of substitution of thepyrrole, 2c,e showed no diastereoselectivity.",

author = "M.T. Maghsoodlou and R.C. Faramarz and {Sayed Mostafa}, H.K. and K. Maryam and Mohamed Makha",

year = "2008",

language = "English",

volume = "27",

pages = "105--113",

journal = "Iranian Journal of Chemistry and Chemical Engineering",

issn = "1021-9986",

publisher = "Iranian Journal of Chemistry and Chemical Engineering",

number = "1",

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TY - JOUR

T1 - Synthesis of Pyrrole Phosphonate Esters: Emphasis on Pyrrole NH Acids and Dialkylacetylenic Esters Substitution

AU - Maghsoodlou, M.T.

AU - Faramarz, R.C.

AU - Sayed Mostafa, H.K.

AU - Maryam, K.

AU - Makha, Mohamed

PY - 2008

Y1 - 2008

N2 - Reaction of dialkyl acetylenedicarboxylates 1a-c and pyrrole derivatives 2a-e in thepresence of triphenylphosphite (TPP) was investigated and the effect of the pyrrole substitution wasestablished. Diastereoselectivity is observed with pyrroles, 2a,b, yielding phosphonate esterderivatives 3a-f and 4, and their relative configuration is determined by 1H/13C and 31P NMR andconfirmed by single X-ray diffraction. Similar reactions with higher degree of substitution of thepyrrole, 2c,e showed no diastereoselectivity.

AB - Reaction of dialkyl acetylenedicarboxylates 1a-c and pyrrole derivatives 2a-e in thepresence of triphenylphosphite (TPP) was investigated and the effect of the pyrrole substitution wasestablished. Diastereoselectivity is observed with pyrroles, 2a,b, yielding phosphonate esterderivatives 3a-f and 4, and their relative configuration is determined by 1H/13C and 31P NMR andconfirmed by single X-ray diffraction. Similar reactions with higher degree of substitution of thepyrrole, 2c,e showed no diastereoselectivity.

M3 - Article

VL - 27

SP - 105

EP - 113

JO - Iranian Journal of Chemistry and Chemical Engineering

JF - Iranian Journal of Chemistry and Chemical Engineering

SN - 1021-9986

IS - 1

ER -

Synthesis of Pyrrole Phosphonate Esters: Emphasis on Pyrrole NH Acids and Dialkylacetylenic Esters Substitution

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