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Substituted γ‐Lactones. 35 . Reduction of 4‐aroyl‐3‐hydroxy‐2(5 H )‐furanones
Author(s) -
Zimmer Hans,
Manning M. J.,
Ventura M.,
Amer Adel,
El Massry Abdel Monem
Publication year - 1986
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.5570230142
Subject(s) - chemistry , sodium borohydride , yield (engineering) , lactone , hydroxymethyl , medicinal chemistry , formaldehyde , organic chemistry , catalysis , materials science , metallurgy
The reduction of 4‐aroyl‐3‐hydroxy‐2(5 H )‐furanons 1a‐c was investigated using different reducing agents. Sodium borohydride reacts with type 1 compounds by loss of water to yield 4‐(arylmethylene)‐2,3(4 H ,5 H )‐furandiones 2a‐c . Platinum or charcoal supported by pallodium chloride transforms 1a to 4‐benzyl‐3‐hydroxy‐2(5 H )‐furanone ( 3). Compounds 2a and 2b react with o ‐phenylenediamine to give 3‐( E ‐(1′‐hydroxymethyl‐2′‐aryl)ethenyl]‐2‐quinoxalinones 4a and 4b . The lactone 3 under the same conditions splits out formaldehyde and forms 3‐(2′‐phenylethyl)‐2‐quinoxalinone ( 6 ). The structure assignments of the novel compounds are based on elemental analysis and nmr as well as ir spectroscopic data.