Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Journal of Organic Chemistry called Nuclear magnetic resonance studies on σ-adducts of heterocyclic systems with nucleophiles. 18. Proton and carbon-13 nuclear magnetic resonance investigations on σ-adduct formation between 1,X-naphthyridines and some methyl-1,8-naphthyridines with potassium amide in liquid ammonia, Author is Van der Plas, H. C.; Van Veldhuizen, A.; Wozniak, M.; Smit, P., which mentions a compound: 1569-17-1, SMILESS is CC1=C2C=CC=NC2=NC=C1, Molecular C9H8N2, Category: naphthyridine.
The 1,5-, 1,6-, and 1,8-naphthyridines dissolved in liquid NH3 containing KNH2 showed the H-2 and C-2 resonance at about 4 and 90 ppm higher field, resp., than the H-2 and C-2 resonance of the naphthyridines observed in CDCl3 as NH2- added to all 3 naphthyridines at C-2 to give a 2-amino-1,2-dihydro-1,X-naphthyridinide ion. The 1,7-naphthyridine showed a more complex reactivity pattern toward NH2-. Besides addition at C-2, addition at C-6 and at C-8 is observed The relation of this study with that of the Chichibabin amination of the 1,X-naphthyridines is discussed. NH2- and 2-methyl- and 4-methyl-1,8-naphthyridine gave only deprotonation of the Me group; 3-methyl-1,8-naphthyridine and NH2- gave the 2-amino-1,2-dihydro-3-methyl-1,8-naphthyridinide ion.
In addition to the literature in the link below, there is a lot of literature about this compound(4-Methyl-1,8-naphthyridine)Category: naphthyridine, illustrating the importance and wide applicability of this compound(1569-17-1).
Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem