Modular synthesis of heterocyclic carbene precursors

Attila Paczal, Attila C. Bényei, András Kotschy

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Abstract

A series of N-heterocyclic carbene precursors, containing an imidazoline or tetrahydropyrimidine framework, were prepared from ω-chloroalkanoyl chlorides. The sequential attachment of nitrogen nucleophiles and subsequent ring closure gave, depending on the reagents used, either the desired dihydroimidazolium and tetrahydropyrimidinium salts or their parent heterocycles. In this latter case, the second substituent was introduced in an alkylation step. The preparation of carbene precursors bearing chiral or bulky substituents was achieved with comparable efficiency.

Original languageEnglish
Pages (from-to)5969-5979
Number of pages11
JournalJournal of Organic Chemistry
Volume71
Issue number16
DOIs
Publication statusPublished - Aug 1 2006

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ASJC Scopus subject areas

  • Organic Chemistry

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