Oxiranes in the Ritter Reaction. Synthesis of 6,7- and 5,8-Dimethoxy-3,3-dialkyl-3,4-dihydroisoquinolines by a Tandem Alkylation-Cyclization Reaction |
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| Authors: | V. A. Glushkov S. N. Shurov O. A. Maiorova G. A. Postanogova E. V. Feshina Yu. V. Shklyaev |
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| Affiliation: | (1) Institute of Technical Chemistry, Urals Branch, Russian Academy of Sciences, Perm, 614600, Russia;(2) Perm State University, Perm, 614600, Russia |
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| Abstract: | The interaction of 1,2- or 1,4-dimethoxybenzene with isobutylene oxide and nitriles RCN leads to 1-R-6,7- or 1-R-5,8-dimethoxy-3,3-dimethyl-3,4-dihydroisoquinolines. In the case of 1,2-dimethoxybenzene and cyclohexene oxide the similar reaction is accompanied by rearrangement and 1-R-3,3-tetramethylene-3,4-dihydroisoquinolines are formed in low yield. On using cyanoacetic acid ester and any oxide derivatives of tetrahydroisoquinolylideneacetic acid are formed. |
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| Keywords: | veratrole 1,4-dimethoxybenzene isoquinoline nitriles oxiranes alkylation quantum chemical calculations AM1 method Ritter reaction cyclization |
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