Table 2. Oxidative Condensation of 4-Halo-1,2,3-benzenetriols with N-Alkylbenzene-1,2-diamine^a.

entry	1,2-diamine	4-halo-1,2,3-benzenetriols	product	yield (%)b
1c	5	9	2c	20
2d	6	9	3c	21
3d	4	10	1b	18
4c	5	10	2b	10
5d	6	10	3b	15

^aUnless otherwise noted, reactions were performed at rt, with O₂ bubbling or under an oxygen atmosphere, using N-alkylbenzene-1,2-diamine (30.0 mg) and 4-halo-1,2,3-benzenetriols (1.0 equiv) in the presence of Cs₂CO₃ (1.0 equiv).

^bIsolated yield.

^cThe reaction was performed with oxygen bubbling.

^dThe reaction was performed under an oxygen atmosphere.