Reaction of substituted 2-vinylpyridines with azo dienophiles
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The reaction of 2-(1-alkoxyvinyl)pyridines with dimethyl azodicarboxylate proceeds primarily via a scheme involving addition to the vinyl substituent to give a mixture of cis- and trans-2-[1-alkoxy-2-(N, N'-dicarbomethoxyhydrazino)-vinyl] pyridines, which undergo partial reaction with a second molecule of azodicarboxylic acid ester via a 1, 4-cycloaddition scheme to give substituted 1, 2, 3, 4-tetrahydro-5-azacinnolines. 2-(1-Bromovinyl)pyridine does not react with dimethyl azodicarboxylate. 1-Phenyl-1, 3, 4-triazoline-2, 5-dione reacts with 2-(1-alkoxyvinyl)pyridines also via a scheme involving addition to the vinyl substituent, and its reaction with 2-(1-bromovinyl)pyridine gives 1, 2-bis (carbomethoxy)-1, 2-dihydro-5-azacinnoline.
KeywordsEster Organic Chemistry Pyridine Dimethyl Vinyl
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