Tetrahedron letters

A synthesis of quinoline-5, 8-quinones via the benzannulation of 1, 4-dihydro-2-pyridyl carbene complexes

GA Peterson, WD Wulff

Index: Peterson, Glen A.; Wulff, William D. Tetrahedron Letters, 1997 , vol. 38, # 32 p. 5587 - 5590

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Citation Number: 14

Abstract

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 ...