Deady, Leslie W. published the artcileA search for lone-pair interactions in forward and reverse Menshutkin reactions of some diaza heterocycles, Application of 2,7-Dimethyl-1,8-naphthyridine, the publication is Australian Journal of Chemistry (1981), 34(1), 163-70, database is CAplus.
The rates of methylation (forward reaction) of phthalazine (I), 1,8-naphthyridine (II), 1,10-phenanthroline (III), and some ring-methylated derivatives are compared with the rates of demethylation of the corresponding N-Me quaternary iodides. In II, and especially in III, an N lone pair in place of a CH group (quinoline and 8-methylquinoline, resp.) aids the forward reaction but does not retard the reverse process. In contrast to III, 2,2′-bipyridine showed behavior typical of α-substituted pyridines. The introduction of a 2-Me group into III had an appreciable rate-enhancing effect on methylation (at N-10), which is interpreted as evidence for lone-pair cooperativity in the forward reaction.
Australian Journal of Chemistry published new progress about 14903-78-7. 14903-78-7 belongs to naphthyridine, auxiliary class 6.6_Aromatics,Naphthyridines, name is 2,7-Dimethyl-1,8-naphthyridine, and the molecular formula is C10H10N2, Application of 2,7-Dimethyl-1,8-naphthyridine.
Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem