Chemistry of Heterocyclic Compounds. 61. Synthesis and Conformational Studies of Macrocycles Possessing 1,8- or 1,5-Naphthyridino Subunits Connected by Carbon-Oxygen Bridges

Article abstract of DOI:10.1021/jo00318a001

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.