A SYNTHESIS OF QUINOLINE-5,8-QUINONES VIA THE BENZANNULATION OF 1,4-DIHYDRO-2-PYRIDYL CARBENE COMPLEXES

Authors
PETERSON GA WULFF WD
Citation
Ga. Peterson et Wd. Wulff, A SYNTHESIS OF QUINOLINE-5,8-QUINONES VIA THE BENZANNULATION OF 1,4-DIHYDRO-2-PYRIDYL CARBENE COMPLEXES, Tetrahedron letters, 38(32), 1997, pp. 5587-5590
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
32
Year of publication
1997
Pages
5587 - 5590
Database
ISI
SICI code
0040-4039(1997)38:32<5587:ASOQVT>2.0.ZU;2-O
Abstract
A method for the preparation of quinoline-5,8-quinones is described wi th 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 th eir reactions with alkynes to provide 1,4-dihydroquinolines. The latte r are convened to quinoline,5,8-quinones by a two-step oxidation proce dure involving eerie ammonium nitrate and trityl tetrafluoroborate. (C ) 1997 Elsevier Science Ltd.