Efficient pyrrole synthesis using double nucleophilic addition to alpha,beta-unsaturated imines with plural nucleophiles |
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| Authors: | Shimizu Makoto Takahashi Atsushi Kawai Shiho |
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| Institution: | Department of Chemistry for Materials, Graduate School of Engineering, Mie University, Tsu, Mie 514-8507, Japan. mshimizu@chem.mie-u.ac.jp |
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| Abstract: | reaction: see text] 2,3,5-Trisubstituted pyrroles were prepared in a regioselective manner using the double nucleophilic addition of alpha,alpha-dialkoxy ketene silyl acetals and ketene sily thioacetals or trimethylsilyl cyanide to alpha,beta-unsaturated imines followed by acid-promoted cyclization and oxidation with DDQ. Using this methodology an imidazole glycerol phosphate dehydratase inhibitor (IGPDI) possessing a monopyrrole aldehyde moiety was synthesized. |
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