SYNTHESIS OF EPOXYISOINDOLO[1,2-<i>a</i>]ISOQUINOLINIUM SALTS BY AN INTRAMOLECULAR [2+4] CYCLOADDITION REACTION IN 2-ALLYL-1-FURYLISOQUINOLINIUM HALIDES

Authors

  • Ф. И. Зубков Peoples' Friendship University of Russia
  • В. П. Зайцев Peoples' Friendship University of Russia
  • М. Д. Обушак Ivan Franko Lviv National University
  • Ю. Д. Ершова Peoples' Friendship University of Russia
  • Д. Ф. Мерцалов Peoples' Friendship University of Russia
  • Е. А. Сорокина Peoples' Friendship University of Russia
  • Е. В. Никитина Peoples' Friendship University of Russia
  • Ю. И. Горак Ivan Franko Lviv National University
  • Р. З. Лытвын Ivan Franko Lviv National University
  • А. В. Варламов Peoples' Friendship University of Russia

DOI:

https://doi.org/10.1007/151

Keywords:

alkaloids, allyl halides, furan, isoindolo[1, 2-a]isoquinolines, intramolecular [2 4] cycloaddition

Abstract

We examined the tandem alkylation/[2+4] cycloaddition of 1-(2-furyl)-3,4-dihydroisoquinolines by various allyl halides. It was found that the process occurred through the intermediate formation of 2-allyl-1-furyl-3,4-dihydroisoquinolinium salts with a subsequent intramolecular exo addition of the allyl fragment to the furan ring. The adducts obtained were structural analogs of the isoindolo[1,2-a]isoquinoline alkaloids jamtine and hirsutine.

Authors: F. I. Zubkov, V. P. Zaytsev, M. D. Obushak, Yu. D. Ershova, D. F. Mertsalov, E. A. Sorokina, E. V. Nikitina, Yu. I. Gorak, R. Z. Lytvyn, and A. V. Varlamov

English Translation in Chemistry of Heterocyclic Compounds, 2013, 49 (5), pp 746-759

http://link.springer.com/article/10.1007/s10593-013-1306-1

Author Biographies

Ф. И. Зубков, Peoples' Friendship University of Russia

Федор Иванович Зубков

В. П. Зайцев, Peoples' Friendship University of Russia

Владимир Петрович Зайцев

М. Д. Обушак, Ivan Franko Lviv National University

Микола Дмитрович Обушак

Ю. Д. Ершова, Peoples' Friendship University of Russia

Юлия Дмитриевна Ершова

Д. Ф. Мерцалов, Peoples' Friendship University of Russia

Дмитрий Федорович Мерцалов

Е. А. Сорокина, Peoples' Friendship University of Russia

Елена Анатольевна Сорокина

Е. В. Никитина, Peoples' Friendship University of Russia

Евгения Валентиновна Никитина

Ю. И. Горак, Ivan Franko Lviv National University

Юрий Игорович Горак

Р. З. Лытвын, Ivan Franko Lviv National University

Роман Зиновиевич Лытвын

А. В. Варламов, Peoples' Friendship University of Russia

Алексей Васильевич Варламов

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Published

2013-04-30

Issue

No. 5 (2013)

Section

Original Papers