Substituent effects on the tautomer ratios between the enamine and methylene imine forms in side‐chained quinoxalines | Zendy

Kurasawa Yoshihisa | Zendy; Miyashita Ryuichiro | Zendy; Takada Atsushi | Zendy; Kim Ho Sik | Zendy; Okamoto Yoshihisa | Zendy

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Substituent effects on the tautomer ratios between the enamine and methylene imine forms in side‐chained quinoxalines

Author(s) -

Kurasawa Yoshihisa,

Miyashita Ryuichiro,

Takada Atsushi,

Kim Ho Sik,

Okamoto Yoshihisa

Publication year - 1995

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.5570320249

Subject(s) - chemistry , tautomer , trifluoroacetic acid , sulfoxide , enamine , substituent , methylene , dimethyl sulfoxide , imine , medicinal chemistry , organic chemistry , catalysis

The p ‐ and m ‐substituted 3‐arylcarbamoylmethylene‐2‐oxo‐1,2,3,4‐tetrahydroquinoxalines 3a‐o showed the tautomeric equilibria between the enamine C and methylene imine D forms in dimethyl sulfoxide or dimethyl sulfoxide/trifluoroacetic acid media. The linear correlation of the Hammett σ p and σ m values with the log K T values was observed in the dimethyl sulfoxide/trifluoroacetic acid (2:1) media of compounds 3a‐o , wherein K T meaned the tautomeric equilibrium constants ([D]/[C]).

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