Highly efficient and expedient synthesis of 5-hydroxy-1H-pyrrol-2-(5H)-ones from FeCl3-catalyzed tandem intramolecular enaminic addition of tertiary enamides to ketones and 1,3-hydroxy rearrangement.
Catalyzed by FeCl(3) under very mild conditions, tertiary enamides underwent a highly efficient intramolecular enaminic addition reaction to the ketonic carbonyls followed by 1,3-hydroxy rearrangement to produce 5-hydroxy-1H-pyrrol-2(5H)-ones in excellent yields.
Yang
Luo
L
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Lei
Chuan-Hu
CH
Wang
De-Xian
DX
Huang
Zhi-Tang
ZT
Wang
Mei-Xiang
MX
D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D005290:Ferric Compounds / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000577:Amides; D002712:Chlorides; D005290:Ferric Compounds; D007659:Ketones; D011758:Pyrroles; C024555:ferric chloride