Premium
Preparation and reactions of 3,4‐dihydro‐2 H ‐pyran‐2‐ones
Author(s) -
ElKholy Ibrahim ElSayed,
Mishrikey Morcos Michael,
AbdoulEla Salah Loutfi
Publication year - 1982
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570190615
Subject(s) - chemistry , pyran , nucleophile , cinnamates , dehydrogenation , ammonium acetate , organic chemistry , ring (chemistry) , michael reaction , sulfur , hydrolysis , medicinal chemistry , catalysis , high performance liquid chromatography
The Michael reaction of ethyl cinnamates with deoxybenzoin gave ethyl 3,4,5‐triaryl‐5‐oxopentanoates which were hydrolysed to the corresponding acids. The latter could be cyclized to the respective 3,4‐dihydro‐2 H ‐pyran‐2‐ones which underwent ring opening with several nucleophiles to the corresponding acid derivatives. However, their reaction with ammonium acetate led to the formation of 3,4‐dihydro‐2‐pyridones. The 3,4‐dihydro‐2‐pyrones and pyridones were dehydrogenated to the corresponding 2‐pyrones and 2‐pyridones by fusion with sulfur.