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

Authors

  • B. А. Глушков Institute of Technical Chemistry, Urals Branch, Russian Academy of Sciences, Perm 614600
  • C. H. Шуров Perm State University, Perm 614600
  • O. А. Mайорова Institute of Technical Chemistry, Urals Branch, Russian Academy of Sciences, Perm 614600
  • Г. А. Поcтаногова Institute of Technical Chemistry, Urals Branch, Russian Academy of Sciences, Perm 614600
  • E. В. Фешина Institute of Technical Chemistry, Urals Branch, Russian Academy of Sciences, Perm 614600
  • Ю. B. Шкляев Institute of Technical Chemistry, Urals Branch, Russian Academy of Sciences, Perm 614600

Keywords:

veratrole, 1,4-dimethoxybenzene, isoquinoline, nitriles, oxiranes, alkylation, quantum chemical calculations, AM1 method, Ritter reaction, cyclization

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.

How to Cite
Glushkov, V. A.; Shurov, S. N.; Maiorova, O. A.; Postanogova, G. A.; Feshina, E. V.; Shklyaev, Yu. V. Chem. Heterocycl. Compd. 2001, 37, 444. [Khim. Geterotsikl. Soedin. 2001, 492.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1017643703041

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Published

2001-04-25

Issue

No. 4 (2001)

Section

Original Papers