The elimination of an alkoxy group in the photo-Graebe–Ullmann conversion of 1-(2,5-dialkoxyphenyl)triazolopyridines into carbolines, and the preparation of α-, γ- and δ-carboline quinones
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 11,p. 1261-1267
- https://doi.org/10.1039/p19930001261
Abstract
Photochemical decomposition of 1-(2,5-dialkoxyphenyl)triazolopyridines 7a, 21 and 33 resulted in elimination of an alkoxy group to give the alkoxycarbolines 9a and 35 in addition to the expected dialkoxycarbolines. The carbolines having either a methoxy and a isopropoxy substltuent 22, 34a and 34b or two methoxy groups 41 were oxidised with ceric ammonium nitrate to yield the α-, γ- or δ-carboline p-quinones 37, 38 and 42.Keywords
This publication has 10 references indexed in Scilit:
- Generation and rearrangement of 4aH-carbazolesJournal of the Chemical Society, Perkin Transactions 1, 1985
- Routes to mitomycins. Application of iminium salts to the synthesis of naphthoquinone mitosene analogsThe Journal of Organic Chemistry, 1980
- Synthesis of 1-substituted ellipticines by a new route to pyrido[4,3-b]carbazolesJournal of the Chemical Society, Perkin Transactions 1, 1979
- Synthesis and analgesic activity of 1,3-dihydro-3-(substituted phenyl)imidazo[4,5-b]pyridin-2-ones and 3-(substituted phenyl)-1,2,3-triazolo[4,5-b]pyridinesJournal of Medicinal Chemistry, 1978
- Photochemical decomposition of 1H-1,2,3-triazole derivativesJournal of the American Chemical Society, 1968
- 85. Nucleophilic displacement reactions in aromatic systems. Part I. Kinetics of the reactions of chloronitropyridines with aromatic amines and with pyridineJournal of the Chemical Society, 1952
- 240. The relative directive powers of groups of the forms RO and RR′N in aromatic substitution. Part X. The nitration of 4-tert.-butoxyanisole and 4-isopropoxyanisoleJournal of the Chemical Society, 1936
- LI.—The relative directive powers of groups of the form RO and RR′N in aromatic substitution. Part III. The nitration of some p-alkyloxyanisolesJournal of the Chemical Society, 1926
- Ueber Phenylirungen bei Gegenwart von Kupfer als KatalysatorEuropean Journal of Inorganic Chemistry, 1906
- Ueber eine neue CarbazolsyntheseEuropean Journal of Organic Chemistry, 1896