Manganese(III) Acetate-Induced Formation of a Fused, Chloro-Substituted β-Lactam Derivative From a Chloroacetamide

Abstract

Reaction of 1-chloroacetyl-5-methoxy-2,3-dihydro-1H-dibenzo[de,h]quinoline (1) with manganese(III) acetate in acetic acid at 50° gave the novel fused spiro derivative 11-chloro-4-methoxy-1,2-dihydro-6H-azeto[2,1-f]dibenzo[de,h]quinoline-6,12(11H)-dione (6) in 21% yield, together with 5-methoxy-7H-dibenzo[de,h]quinolin-7-one (3), 5-methoxy-2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one (4), and 1- chloroacetyl-5-methoxy-2,3-dihydro-1H-dibenzo[de,h]-quinolin-7-yl ethanoate (5) in 1, 3 and 44% yields respectively. Compound (5) was shown to be a precursor of (3), (4) and (6).