Tetrahedron Letters p. 5587 - 5590 (1997)
Update date:2022-08-11
Topics:
Peterson, Glen A.
Wulff, William D.
A method for the preparation of quinoline-5,8-quinones is described with the key step the benzannulation of a dihydropyridyl Fischer carbene complex. The carbene complexes are generated by the standard Fischer method upon metallation of N-Boc protected 1,4-dihydropyridines and their reactions with alkynes to provide 1,4-dihydroquinolines. The latter are converted to quinoline,5,8-quinones by a two-step oxidation procedure involving eerie ammonium nitrate and trityl tetrafluoroborate.
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(1997)