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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- 1.P. B. Terent'ev, A. N. Kost, and V. G. Kartsev, Khim. Geterotsikl. Soedin., No. 5, 702 (1976).Google Scholar
- 2.P. B. Terent'ev, V. G. Kartsev, and A. N. Kost, Khim. Geterotsikl. Soedin., No. 7, 976 (1976).Google Scholar
- 3.B. Oisen, Systematische Studien von Azodicarbonsäuren, Köln (1960).Google Scholar
- 4.P. B. Terent'ev and N. G. Kotova, Khim. Geterotsikl. Soedin., No. 5, 647 (1978).Google Scholar
- 5.I. Bourdais, F. Cudnut, and I. C. Prin, Bull. Soc. Chim. France, No. 3, 50 (1964).Google Scholar
- 6.R. S. Cookson, S. S. Rupte, and I. D. R. Sevens, Organic Synthesis, Vol. 51 (1971), p. 121.Google Scholar