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

Document Type : Research Article


1 Department of Chemistry, University of Sistan & Baluchestan, P.O. Box 98135-674 Zahedan, I.R. IRAN

2 High Education Center, Gorgan University of Agricultural Sciences and Natural Resources, P.O.Box 163, Gonbad, I.R. IRAN


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


Main Subjects

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