In the title compound, C28H28N6O, the naphthyridine moiety is planar and the pyrrolidine ring adopts a half-chair conformation. The dimethylaminophenyl substituent is nearly orthogonal to the naphthyridine moiety, while the methoxyphenyl ring is twisted from it by 11.3 (2)°. The molecular structure is stabilized by an N—H⋯π interaction. In the solid state, the inversion-related molecules are linked to form N—H⋯N hydrogen-bonded dimers. The molecular packing is stabilized by weak C—H⋯π and π–π interactions.
[Show abstract][Hide abstract] ABSTRACT: A unique mean plane is defined for a general monocyclic puckered ring. The geometry of the puckering relative to this plane is described by amplitude and phase coordinates which are generalizations of those introduced for cyclopentane by Kilpatrick, Pitzer, and Spitzer. Unlike earlier treatments based on torsion angles, no mathematical approximations are involved. A short treatment of the four-, five-, and six-membered ring demonstrates the usefulness of this concept. Finally, an example is given of the analysis of crystallographic structural data in terms of these coordinates.
Journal of the American Chemical Society 03/1975; 97(6). DOI:10.1021/ja00839a011 · 12.11 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: The title compound has antibacterial properties. The piperazine fragment, possessing a chair conformation, is almost fully extended with respect to the naphthyridine ring plane, the dihedral angle between these two planes being 27.9 (3)degrees.
[Show abstract][Hide abstract] ABSTRACT: Besides the expected pyridinedicarboxylate (4), triethyl 2,7,8a-trimethyl-1,4,4a,5,8,8a-hexahydro-1,8-naphthyridine-3,4a,6-tricarboxylate (6) was also isolated in the Hantzsch pyridine synthesis starting from ethyl acetoacetate and hexamethylenetetramine in acetic acid. The 1,8-naphthyridine (6) was probably formed in the [4 + 2]cycloaddition of heterodiene (5) and the 1,4-dihydropyridinedicarboxylate (3). The observed regioselectivity was explained in terms of simple Hückel molecular orbital calculations. Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate (4) gave ethyl 2-methyl-5-oxo-5,6-dihydro-1,6-naphthyridine-3-carboxylate (9) in high yield in a one-step reaction with 1,3,5-triazine in the presence of ethanolic sodium ethoxide, or in a two-step procedure with DMF diethyl acetal followed by ring closure with ammonia.
Journal of the Chemical Society Perkin Transactions 1 05/1986; 1:753-757. DOI:10.1039/P19860000753 · 1.95 Impact Factor
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