規那塩基誘導体の合成 (第25報)

規那塩基の2´-置換体の合成

抄録

When the mono- and di-salt of the ar -N-oxide of quinine or dihydroquinine is warmed with phosphoryl chloride in chloroform, 2′-chloroquinine or -dihydroquinine is formed, as in the case of the free base. Mono salt gives a better result and the monothiocyanate, an intermediate in the synthesis of the N-oxide of quina base, is the most suitable since it gives the 2′-chloro compound in about 90% yield. Application of sodium methoxide, phenoxide, methanethioid, and piperidine to 2′-chloroquinine and -dihydroquinine yields the corresponding 2′-methoxy, -phenoxy, -thiomethyl, and N′-piperidyl derivatives.