Quinolizines. Part XII. Reactions of some 1- and 2-aminoquinolizinium salts

Abstract

Bromination of the 1- or 2-aminoquinolizinium salts (I)–(IV) gave monobromo-amines (VII), (IX), and (XI)–(XIII); 1-amino-3-methylquinolizinium bromide (III) also gave a dibromo-amine (X). Under more forcing conditions a 2,3-disubstituted 1-acetamidoquinolizinium salt (VI) gave a brominated amide (VIII). Nitrous acid treatment of the amines gave two tricyclic systems; the 2,3-dimethyl-substituted amines (I) and (VII) gave pyrazoloquinolizinium salts (XIV) and (XV), while the 3-methyl substituted amine (III) gave an oxadiazoloquinolizine (XIX).