BENZOLACTAMS-1. ALKYLATION OF 1,2,4,5-TETRAHYDRO-3-METHYL-3H-3-BENZAZEPIN-2-ONE WITH SODIUM HYDRIDE AND ALKYL HALIDE

Article abstract of DOI:10.1016/0040-4020(80)80055-X

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 (2l) and benzyl (2m-o) derivatives, in satisfactory yields, and secondary halides resulted in lower yields (2h,i) than primary halides.In attempted dialkylations with ω,ω'-dibromoalkanes, 5- and 6-membered spiro products (4c,d) were obtained by this method.The Michael type addition reaction was also studied and it was found that acrylic acid esters gave the corresponding adducts (2p,q).