Synthetic Studies on the Biologically Active 3-Benzazepines

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1. A series of (methylsulfinyl)acetamides reacted with electron-rich arenes in the presence of p-toluenesulfonic acid to give alpha-(methylthio)aryl- acetamides, some of which were transformed into biologically active aryl- ethylamines such as (<plus-minus>)-macromerin2.1,3,4,5-Tetrahydro-2H-3-benzazepin-2-one derivatives were synthesized by an acid-catalyzed cyclization of N-(2-arylethyl)-N-methyl-2-sulfinylacet- amides. Some chemical transformations of the 2H-3-benzazepin-2-ones were also investigated.3. Synthesis of 1,3,5,6,9,15-hexahydro-4H-1,3-dioxolo[4,5-h]pyrrolo[2,1-b]- [3]benzazepin-2(1H),8-dione, a key intermediate for the total synthesis of (<plus-minus>)-cephalotaxine, has been achieved in a stereoselective manner by a synthetic sequence involving an acid-catalyzed cylization of the alpha- sulfinylacetamide as a key ste