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Synthesis 1988; 1988(12): 999-1001
DOI: 10.1055/s-1988-27785
DOI: 10.1055/s-1988-27785
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Synthesis of N-Substituted Pyrroles From Azlactones via 1,3-Oxazolium 5-Oxides
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Publication Date:
20 August 2002 (online)
In situ N-alkylation of azlactones (1,3-oxazol-5(4H)-ones) with reactive alkylating agents has been successfully accomplished. The resulting mesoionic 1,3-oxazolium 5-oxides (munchnones) are further transformed into N-alkylated pyrroles via a 1,3-dipolar cycloaddition reaction with a dipolarophile (dimethyl acetylenedicarboxylate) in the presence of 2,6-di-tert-butylpyridine.