A novel synthesis of aromatic methoxy and methylenedioxy substituted 2,3,4,5‐tetrahydro‐1H‐3‐benzazepines

Abstract

A new synthesis of aromatic methoxy and methylenedioxy substituted 2,3,4,5‐tetrahydro‐1H‐3‐benzazepines is described. Suitably substituted phenethylamines and their α‐methyl homologs in the form of their N‐acetyl derivatives are chloromethylated, the resulting benzyl chlorides are reacted with cyanide and hydrolysis of the latter yields 2‐(2‐aminoethyl)phenylacetic acid derivatives. Thermal cyclization yields the corresponding lactams. Hydride reduction of these lactams furnishes the substituted 2,3,4,5‐tetrahydro‐1H‐3‐benzazepines which may be methylated on nitrogen by formaldehyde and hydrogen. By this sequence a number of previously unde‐scribed compounds have been prepared.

A Fluorous, Pummerer Cyclative‐Capture Strategy for the Synthesis of N‐Heterocycles

“…Thus, treatment of 4- (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylsulfanyl)-2-methyl-1,2-dihydroisoquinolin-3(4H)one (9) (153 mg, 0.24 mmol, 1 equiv) in THF (5 mL) with SmI 2 (6.0 mL of a 0.1 m solution in THF, 0.60 mmol, 2.5 equiv) and purification by using fluorous silica gel gave the title compound (39 mg, 0.18 mmol, 74 %) as a yellow oil. 1 [34] General procedure C was followed. Thus, treatment of 14 (0.12 g, 0.14 mmol, 1 equiv) with SmI 2 (6.34 mL, 0.1 m solution in THF, 0.63 mmol, 4.4 equiv) and purification by using fluorous silica ( [M] + .…”