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.
| Identifer | oai:union.ndltd.org:BGMYU2/oai:scholarsarchive.byu.edu:etd-9184 |
| Date | 01 August 1977 |
| Creators | Carlock, John Timothy |
| Publisher | BYU ScholarsArchive |
| Source Sets | Brigham Young University |
| Detected Language | English |
| Type | text |
| Format | application/pdf |
| Source | Theses and Dissertations |
| Rights | http://lib.byu.edu/about/copyright/ |
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