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Synthesis and interconversion of 6‐aroyl‐4‐oxohexanoie acids and 5‐aryl‐2‐furanpropionic acids. Antiinflammatory agents
Author(s) -
Short Franklin W.,
Rockwood Gail M.
Publication year - 1969
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.5570060519
Subject(s) - chemistry , aryl , solvolysis , medicinal chemistry , organic chemistry , rationalization (economics) , hydrolysis , philosophy , alkyl , epistemology
A series of 6‐aroyl‐4‐oxohexanoic acids ( 2 ) was prepared for intermediate use by acid‐catalyzed solvolysis of substituted 3‐(2‐furyl)acrylophenones ( 1 ). This reaction occasionally gave 5‐aryl‐2‐furanpropionic acids ( 3 ) instead of, or in addition to, the desired diketones ( 2 ). Equilibrium between 2 and 3 was observed in the case where Ar is m ‐nitrophenyl. A rationalization for the formation of 3 is offered, and published reports with which our results differ are discussed. Diketones ( 2 ) were cyclized to furans ( 3 ) and antiinflammatory screening data are reported for the latter.