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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)105-113
JournalIranian Journal of Chemistry and Chemical Engineering
Volume27
Issue number1
Publication statusPublished - 2008

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