ACETALES OF LACTAMS AND AMIDES. 60. N- AND O-ALKYLATION OF 5-OXO-5,6,7,8-TETRAHYDROCARBOSTYRILS. SYNTHESIS OF ISOXAZOLO- AND PYRAZOLOQUINOLINES

Article abstract of DOI:10.1007/BF00633222

The alkylation of 5-oxo-5,6,7,8-tetrahydrocarbostyrils has been examined by GLC.It has been found that, irrespective of the reaction conditions and the alkylating agent used, both N- and O-alkylation occur.When triethyloxonium fluoroborate and N,N-DMF diethyl acetal are used O-alkylation predominates, and with alkyl halides, N-alkylation.Reaction of N-ethyl-5-oxo-5,6,7,8-tetrahydrocarbostyril and 2-ethoxy-5-oxo-5,6,7,8-tetrahydroquinoline with DMF diethyl acetal gives the 6-dimethylaminomethylene derivatives, treatment of which with hydrazine hydrate or hydroxylamine affording isoxazolo<5,4-f>- or pyrazolo<3,4-f>quinolines.