THE ELIMINATION OF AN ALKOXY GROUP IN THE PHOTO-GRAEBE-ULLMANN CONVERSION OF 1-(2,5-DIALKOXYPHENYL)TRIAZOLOPYRIDINES INTO CARBOLINES, AND THE PREPARATION OF ALPHA-CARBOLINE, GAMMA-CARBOLINE AND DELTA-CARBOLINEQUINONES
Lk. Mehta et al., THE ELIMINATION OF AN ALKOXY GROUP IN THE PHOTO-GRAEBE-ULLMANN CONVERSION OF 1-(2,5-DIALKOXYPHENYL)TRIAZOLOPYRIDINES INTO CARBOLINES, AND THE PREPARATION OF ALPHA-CARBOLINE, GAMMA-CARBOLINE AND DELTA-CARBOLINEQUINONES, Journal of the Chemical Society. Perkin transactions. I, (11), 1993, pp. 1261-1267
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 dialkoxycarboli
nes. The carbolines having either a methoxy and a isopropoxy substitue
nt 22, 34a and 34b or two methoxy groups 41 were oxidised with ceric a
mmonium nitrate to yield the alpha, gamma- or delta-carboline p-quinon
es 37, 38 and 42.