Tetrahedron p. 2001 - 2008 (1983)
Update date:2022-08-05
Topics:
Newkome, George R.
Marston, Charles R.
2,6-Bis(bromomethyl)nicotinic oxazoline (15), prepared from ethyl 2,6-dimethylnicotinate, was converted into the 1:1-macrocyclic oxazolines 19 and 22 as well as the isomeric macrocyclic dimers 20.Ethyl 2,6-bis(bromomethyl)nicotinate (23), prepared from 6b, was converted to the corresponding 1:1-dibenzo-18-crown-6 macrocyclic analog 24.NMR and mass spectral data were used to ascertain the macrocyclic structures.Reaction of 22 with EtMgBr afforded, after oxidation, the 4-substituted pyridino macrocycle 26 in high yield.However, under identical conditions, the non-oxazoline macrocycle 27 was recovered in toto.
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