Studies on seven-membered ring compounds. XXIV. Syntheses of 8-methylimino cyclohepta[b]pyrrole and cyclohepta[b]pyrrole-8(1H)-thione derivatives and tropone analogues of tryptamine.

Abstract

8-Methylimino-1, 8-dihydrocyclohepta [b] pyrrole derivatives (XIa∼d) were synthesized by cyclization of azines obtained from 2-methylaminotropone hydrazone and various carbonyl compounds. Direct methylation of cyclohepta [b] pyrrol-8(1H)-one derivatives with dimethyl sulfate resulted in O-methylation affording 8-methoxycyclohepta [b] pyrroles (XVa∼c) which on condensation with methylmine also gave XIa∼c. Cyclohepta [b] pyrrole-8(1H)-thione derivatives were synthesized by reaction of XVa∼c and sodium sulfide. In addition, tropone analogues of tryptamine, 3-(2-aminoethyl) cyclohepta [b] pyrrole derivatives were prepared.