Benzolactams—I: Alkylation of 1, 2, 4, 5-tetrahydro-3-methyl-3h-3-benzazepin-2-one with sodium hydride and alkyl halide

K Orito, T Matsuzaki

Index: Orito, Kazuhiko; Matsuzaki, Tsutomu Tetrahedron, 1980 , vol. 36, # 81 p. 1017 - 1021

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Citation Number: 14

Abstract

Alkylation of 1, 2, 4, 5-tetrahydro-3-methyl-3H-3-benzazepin-2-one 1a with various halides and sodium hydride in tetrahydrofuran-dimethylformamide solvent system was studied. Primary halides predominantly provided the 1-mono-substituted products, such as alkyl (2a- g, p, q), allyl (2j, k), propargyl (21) and benzyl (2m-o) derivatives, in satisfactory yields, and secondary halides resulted in lower yields (2h, i) than primary halides. In attempted ...