115975-86-5Relevant academic research and scientific papers
ALLENES. PART 46. SYNTHESIS OF 1,2-DIHYDRO-4H-3,1-BENZOXAZINES, 4H-3,1-BENZOXAZINES, AND 3-CYANOQUINOLINES FROM ALLENIC AND ACETYLENIC NITRILES
Fomum, Z. Tanee,Nkengfack, A. Ephraim,Landor, Stephen R.,Landor, Phyllis D.
, p. 277 - 282 (2007/10/02)
Allenic nitriles or phenylpropynenitrile react in refluxing ethanol with o-aminobenzyl alcohol to give first enaminic nitriles (2) which slowly cyclise to dihydro-4H-3,1-benzoxazines (3).The latter eliminate acetonitrile on heating to give 4H-3,1-benzoxazines (4) whereas the enaminic nitriles under the same conditions give mainly 2-alkyl-3-cyanoquinolines (5).Mechanistic considerations and spectroscopic details are discussed.
