Abstract
Reaction of (4,7-diazadecane-1,10-diamine)copper(II) or (3,6-diazaoctane-1,8-diamine)nickel(II) ions in alcoholic base with formaldehyde and a variety of carbon acids with nitro-substituents has been studied. The RCH 2NO 2carbon acids 1-nitrododecane, 12-nitrododecanoic acid, 3-nitropropanoic acid, tetrahydro-2-(2′-nitroethoxy)-2H-pyran and nitromethane undergo facile Mannich-type reactions to yield new pendant-arm macrocycles with a NHCH 2C(R)NO 2CH 2NH link built between the two primary amines of the precursor compound. In the case of nitromethane, R in the major product is CH 2OH rather than H, due to further condensation of the residual acidic proton with formaldehyde; otherwise, R is the expected substituent carried through from reaction of the RCH 2NO 2 unit. Zinc/acid reduction of the copper(II) complex of the long-chain pendant macrocycle formed by condensation involving 12-nitrododecanoic acid permitted isolation of 1,4,8,12-cyclopentadecane-10-amine-10-undecanoic acid as the hydrochloride salt.
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