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A novel two-step synthesis of substituted 2-formylpyrroles is described. Aldol adducts of ketones and 4-formyloxazole undergo a dehydration/oxazole hydrolysis/cyclization cascade on sequential treatment with MsCl/Et3N and aqueous NaOH to yield 5-substituted and 4,5-disubstituted 2-formylpyrroles. The methodology was extended to an N-benzyl thiazolium salt.
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Reeves et al. (2007) studied this question.
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