When subjected to ultraviolet radiation in the presence of an alkene, s-triazolo[4,3-b]pyridazine (STP) undergoes an unusual 3 + 2 photocycloaddition wherein the alkene adds to the 1 and 8 positions of STP with concommitant N4-N5 bond cleavage yielding 5,6-disubstituted-6,7-dihydro-7-methylene (and 7-cyanomethyl)-5H-pyrrolo[1,2-b]-s-triazoles. Amides and esters of indole-3-carboxylic acid have been synthesized by a novel reaction employing the ultraviolet irradiation of 3-diazo-4-oxo-3,4-dihydroquinoline (QDA) in the presence of amines or alcohols respectively. QDA, when irradiated, is postulated to undergo an internal Wolff Rearrangement to Indole-3-ketene which can add any amine or alcohol to form the corresponding amide or ester in modest to good yield.
College and Department
Chemistry and Biochemistry
BYU ScholarsArchive Citation
Carlock, John Timothy, "A photochemical study of s-triazolo[4,3-b] pyridazine and 3-diazo-4-oxo-3,4-dihydroquinoline" (1977). Theses and Dissertations. 8184.
Heterocyclic compounds, Photochemistry