Table 1.

Generation of Aza-Anthraquinones via Photoelectrocyclization Reactions

entry	X	Conditions	Coupling Yield	Oxidation Yield	aminoquinone	time (min.)b	quinoline	yield	quinolone	yield
1	CI	A	76%	75%		255		47%		50%
2	OH	B	56%	80%		75		76%		21%
3	OH	B	81%	95%		25		90% (cis:trans = 15:1)		--d
4	CI	A	78%	70%		50		33%		--e
5	OH	B	—	52%c		60		20%		--e
6	OH	B	—	45%c		60		20%		--e

^aConditions: A: Et₃N, CH₂Cl₂; B: EDC·HCl, 4-DMAP, and CH₂Cl₂.

^bTime required for the disappearance of the starting material by thin-layer chromatography (TLC).

^cYield for two steps.

^dA trace amount of 15 was formed if the reaction was allowed to proceed for more than 60 min.

^eAn intractable mixture of what we presume as oxidized byproducts was obtained.