O. Hoshino, Y. Yamanashi, T. Toshioka
Oct 25, 1971
Citations
0
Influential Citations
5
Citations
Journal
Chemical & Pharmaceutical Bulletin
Abstract
4-Cyano- or 4-alkyl-7-hydroxy tetrahydroisoquinolines (V or VI-X, XII, XVIII) were obtained by reaction of 4, 7-diacetate (I) with potassium cyanide or nitromethane-K2CO3 in aqueous solution or with active methylene compounds (malononitrile, acetophenone, cyclohexanone, cyclopentanone, diethyl malonate or dimethylsulfoxide (DMSO) in anhydrous solution (tert-BuOH-KO-tert-Bu, C6H6-NaH or DMSO-NaH). While a diastereoisomeric mixture of IX or XVIII was obtained in the case of cyclohexanone or DMSO, two kinds of diastereoisomer, Xa and Xb (also formed by reaction of I with 2-cyclopentylidene cyclopentanone), could be isolated in the case of cyclopentanone. With respect to diethyl malonate, the reaction afforded 7-acetoxy- and 7-hydroxy-4-alkyl compound (XI and XII). Furthermore, the reaction pathway on formation of XI was inferred.