Condensation of Carboxylic Acids with Non-Nucleophilic N-Heterocycles and Anilides Using Boc2O

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Abstract

A novel condensation reaction of carboxylic acids with various non-nucleophilic N-heterocycles and anilides was developed. The reaction proceeds in the presence of di-tert-butyl dicarbonate (Boc2O), catalytic 4-(dimethylamino)pyridine (DMAP), and 2,6-lutidine and is applicable to the acylation of a wide range of non-nucleophilic nitrogen compounds, including indoles, pyrroles, pyrazole, carbazole, lactams, oxazolidinones, and anilides with high functional group compatibility. The scope of indoles, carboxylic acids, and anilides was also studied.

Original languageEnglish
Pages (from-to)11444-11453
Number of pages10
JournalJournal of Organic Chemistry
Volume81
Issue number22
DOIs
Publication statusPublished - 2016 Nov 18

ASJC Scopus subject areas

  • Organic Chemistry

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