Yoichiro Hoshina

Cyclic amination onto aromatic ring of sulfonamides with (diacetoxyiodo)arenes: Effect of sulfonyl group

Abstract Sulfonamides of primary amine bearing an aromatic ring at γ-position were treated with (diacetoxyiodo)arene and iodine under irradiation conditions with a tungsten lamp to give the corresponding 1,2,3,4-tetrahydroquinoline derivatives in moderate to good yields. The present reaction proceeded under mild and neutral conditions.

Formation and synthetic use of oxygen-centred radicals with(diacetoxyiodo)arenes

o-Alkyl- or o-aryl-benzenecarboxylic acids and alcohols containing an aromatic ring are treated with a (diacetoxyiodo)arene–iodine system to give the corresponding cyclized products such as phthalide, benzocoumarin and chromane derivatives in moderate to good yields via the corresponding oxygen-centred radicals. For the carboxylic acids, [bis(trifluoroacetoxy)iodo]benzene functions effectively, while (diacetoxyiodo)benzene is effective for the alcohols. Chromane and its derivatives are obtained as iodinated compounds by hypoiodite species derived from (diacetoxyiodo)benzene and iodine.

CYCLIC AMINATION ONTO AROMATIC RING VIA RADICAL PATHWAY WITH (DIACETOXYIODO)ARENES

Sulfonamides of primary amine bearing an aromatic ring at γ-position were treated with (diacetoxyiodo)arene and iodine under irradiation conditions with a tungsten lamp to give the corresponding 1,2,3,4-tetrahydroquinoline derivatives in moderate to good yields.