Aromatic rings proton sponges

Aromatic /-amines can act as carbon nucleophiles in reaction with perfluorinated 1,3,5-triazines. Amines used are 1-methylpyrrole, 1-methylindole, l,8-bis(dimethylamino)naphthalene (proton sponge), A,A-dimethyl- and JV,7V-diethyl-aniline. All the amines reacted at the expected position in the ring except A,7V-diethylaniline which also gave some or//io-product not seen with N,N-dimethylaniline (Equation (8)) <92T7939>. 

Incorporation of a dialkylamino group of proton sponge into an aromatic ring such as in quino[7.8-h]quinoline (18) results in an increase in basicity [18,19]. In contrast to... 

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