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Molecular diversity

Synthesis of functionalized 5-imino-2,5-dihydro-furans through the reaction of isocyanides with activated acetylenes in the presence of ethyl bromopyruvate.


PMID 16967197

Abstract

The reaction between alkyl(aryl) isocyanides and dibenzoylacetylene in the presence of ethyl bromopyruvate leads to ethyl 3,4-dibenzoyl-2-bromomethyl-5-alkyl(aryl)imino-2,5-dihydro-furan-2-carboxylates in high yields. Dialkyl acetylenedicarboxylates react with tert-butyl isocyanide and ethyl bromopyruvate to produce 3,4-dialkyl 2-ethyl 2-bromomethyl-5-tert-butylimino-2,5-dihydro-furan-2,3,4-tricarboxylates.