Journal of Organic Chemistry p. 833 - 839 (1981)
Update date:2022-08-11
Topics:
Newkome, George R.
Garbis, Sam J.
Majestic, Veronica K.
Fronczek, Frank R.
Chiari, Giacomo
Polyethereal macrocycles were prepared from both 2,6-dichloro-1,5-naphthyridine (2) and 2,7-dichloro-1,8-naphthyridine (6).The "cross-the-face" structures of 1:1 macrocycles 7, derived from 2, were confirmed by NMR.The 2,7-(1,8-naphthyridino) macrocyclic structures 9 and 10 were also supported by NMR data which were indicative of diminished N-electron density, when compared to the parent 1,8-naphthyridine.Template reactions did not appreciably enhance product yields.The X-ray crystal structure of 1:1 macrocycle 9b was conducted and showed that the imidate moieties possess a nearly 0 deg dihedral angle and that the naphthyridine subunit exhibits marginal deviation from planarity.
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