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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).

A general methodology, i.e. ring destruction with cyanogen bromide and chloroformate ester is applied to the synthesis of the new thiadiazole‐anellated heterocyclophanes (III) and (VI).

Dedicated to Professor Jim Coxon on the occasion of his 65th birthday. AbstractRing distorted 3-aza[5] and 3-aza [6](1,7)naphthalenophanes have been shown to undergo ready Diels-Alder cycloaddition reactions with 4-phenyl-1,2,4-triazoline-3,5-dione, tetracyanoethylene, 1,1-dicyanoethylene and 1,1-diethyl methylenemalonate to form new functionalized polycyclic heterocyclic derivatives. Addition was shown to occur selectively in each case in the less substituted aromatic ring of the naphthalene moiety.

ChemInform Abstract The dibenzoquinolones (I) are reduced and then acylated to give the N-chloroacetyl compounds (IV) which are irradiated to give the bridged cyclization products (V), together with minor amounts of the pentacyclus (VIa). (Intermediates).