P. B. Terent'ev, V. G. Kartsev, A. V. Gorelov
1980
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Chemistry of Heterocyclic Compounds
Abstract
When isomeric 2- and 4-vinylpyridines, as well as 2-methyl-5-vinylpyridine, are heated in polyphosphoric or acetic acid, they undergo dimerization, which proceeds via a 1,4-cycloaddition scheme to give pyridyl-substituted 5,6,7,8-tetrahydroquinclines or isoquinolines. Quantum-chemical calculations with the use of the concepts of molecular orbital perturbation theory make it possible to predict the regiospecificity of the reaction. The regiospecific cross cycloaddition of 4-vinylpyridine to 2-methyl-5-vinylpyridine was proposed theoretically and proven experimentally.