OxiNDOLE, 3-ETHYL-l-METHYL

The formation of cyclopropane derivatives by photolysis of diazoalkanes in the presence of alkenes is believed to occur by photolytic decomposition of the diazoalkane to yield the carbene, followed by addition of this carbene to the alkene. Cycloaddition of this type has been reported in furan, dihydrofuran, and thiophene.198 Thus, photolysis of ethyl diazoacetate in thiophene yields the bicyclic sulfur heterocycle (215). Alternatively, photolysis of 3-diazo-l-methyl-oxindole (216) in cyclohexene leads to the formation of two isomers which are thought to have the spirocyclopropyl structure (217) photolysis in ethanol yields 3-ethoxy-1-methyloxindole.194... 

Ozone bubbled briefly into an ice-cooled soln. of 3-cyano-4-ethyl-4-methyl-l-tosyl-l,4-dihydroquinoline in methylene diloride, and the resulting ozonide refluxed briefly with methanol containing 5%-HCl 3-ethyl-3-methyl-l-tosyl-oxindole. Y ca. 100%. F. e. s. M. Natsume and I. Utsunomiya, Chem. Pharm. Bull. 20, 1595 (1972). 

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