ChemInform Abstract: ALKYLIERUNGS‐, ACYLIERUNGS‐ UND RED.‐VERSUCHE AN 1‐CYAN‐1,2‐DIHYDRO‐ UND ‐1,2,3,4‐TETRAHYDRO‐ISOCHINOLIN‐DERIVATEN

Abstract

Die ,,Dihydro‐Reissert‐Verbindung" (I) reagiert mit NaH in DMF unter Bildung des entsprechenden Carbanions, aus dem mit den Halogeniden (II) bzw. mit Phenylsenföl die in 1‐Stellung substituierten Produkte (III) (26‐98% Ausbeute) bzw. (IV) (73%) entstehen.

Synthesis of 1-(aminomethyl)-1,2,3,4-tetrahydroisoquinolines and their actions at adrenoceptors in vivo and in vitro

“…However, use of the acidic reagent aluminum hydride was also unsuccessful, the major product (14%) being the unexpected l,T-bi(l,2,3,4-tetrahydroisoquinolinyl) (8). Similar products have been reported from the reduction of isoquinolines with aluminum amalgam.24 These problems were finally overcome by reduction of the IV-benzyl derivative (6, R = CH2Ph) with aluminum hydride, resulting in excellent yields of the aminomethyl compound (9), which was readily hydrogenolyzed to the model noradrenaline analogue (10). The model isoproterenol analogue (11) was prepared by reductive alkylation with acetone and sodium cyanoborohydride prior to debenzylation.…”