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3‐Aroylmethyl derivatives of 2(1 H )quinoxalinone and 2 H ‐l,4‐benzoxazin‐2‐ones existing in the enamine form
Author(s) -
Iwanami Yasuo,
Inagaki Takeshi
Publication year - 1976
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.5570130402
Subject(s) - chemistry , enamine , mass spectrum , phenacyl , stereochemistry , medicinal chemistry , amidine , bicyclic molecule , organic chemistry , catalysis , ion
Seventeen derivatives of 2(1 H )quinoxalinone and 2 H ‐l,4‐benzoxazin‐2‐one have been synthesized for structural study. All of the compounds having a substituted phenacyl, isonicotinoylmethyl, or 2‐furoylmethyl side chain are shown to exist in the enamine form with an internal chelation both in the crystalline and solution states as evidenced by the ir and pmr spectra, respectively. In the gas phase, however, o ‐hydroxyphenacyl derivatives can exist in another type of intramolecularly hydrogen‐bonded form which is supported by their mass spectra.