A general synthesis of substituted formylpyrroles from ketones and 4-formyloxazole |
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| Authors: | Reeves Jonathan T Song Jinhua J Tan Zhulin Lee Heewon Yee Nathan K Senanayake Chris H |
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| Institution: | Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc, Ridgefield, CT 06877-0368, USA. jreeves@rdg.boehringer-ingelheim.com |
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| Abstract: | 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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