Efficient pyrrole synthesis using double nucleophilic addition to alpha,beta-unsaturated imines with plural nucleophiles.
[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.
Shimizu
Makoto
M
Department of Chemistry for Materials, Graduate School of Engineering, Mie University, Tsu, Mie 514-8507, Japan. mshimizu@chem.mie-u.ac.jp
Takahashi
Atsushi
A
Kawai
Shiho
S
D002384:Catalysis; D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D006836:Hydro-Lyases / Q000037:antagonists & inhibitors*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism
D004791:Enzyme Inhibitors; D007097:Imines; D017646:Organosilicon Compounds; D011758:Pyrroles; D006836:Hydro-Lyases; C021434:imidazoleglycerolphosphate dehydratase