STEREOSPECIFIC SYNTHESIS OF SOME POLYCYCLIC CIS-β-LACTAMS

Article abstract of DOI:10.1016/0040-4020(80)80195-5

Amides 1 on reaction with P2S5 in pyridine give thioamides 2 which on treatment with methyl iodide afford the corresponding 1-methylthio-3,4-dihydroisoquinolines 3.Annelation of these imines with phenoxyacetyl chloride in the presence of triethylamine furnish 6-methylthio-7-phenoxy-2',3'-dimethoxybenzooctem 4a and 6-methylthio-7-phenoxy-2',3'-methylenedioxybenzooctem 4b respectively.Desulphurisation of these β-methylthio-β-lactams with Raney nickel yield the novel polycylic cis-β-lactams 5a and 5b.