Diaziridines. II. The Addition of Diaziridines to Electrophilic Acetylenes

Harold W. Heine, Thomas It Hoye, Paul G. Williard, Rebecca Cowan Hoye

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25 Scopus citations

Abstract

Addition of 3,3-dialkyl-, 1,3-dialkyl-, and 1,3,3-trialkyldiaziridines to dibenzoylacetylene, diethyl acetylenedi-oarboxylate, and ethyl propiolate gives, generally, adducts in which the diaziridine ring is no longer intact. For example, addition of 1,3-dialkyl- and 1,3,3-trialkyldiaziridines to dibenzoylacetylene forms 2-(alkylidenehydrazino)-l,4-diphenyl-2-butene-l,4-diones (2). Evidence is presented that it is the alkylated nitrogen of 1-methyl-3,3-pentamethylenediaziridine which adds to the triple bond of dibenzoylacetylene. Stereochemical studies show that diaziridines add to ethyl propiolate to give trans adducts. Hydrolysis of 2-(alkylidenehydrazino)-l,4-diphenyl-2-butene-l,4-diones is shown to be a useful method for the preparation of l-alkyl-3-phenyl-5-benzoylpyrazoles.

Original languageEnglish (US)
Pages (from-to)2984-2988
Number of pages5
JournalJournal of Organic Chemistry
Volume38
Issue number17
DOIs
StatePublished - Aug 1 1973

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