Chemoselective Strategy for the Direct Formation of Tetrahydro-2,5-methanobenzo[c]azepines or Azetotetrahydroisoquinolines via Regio- and Stereoselective Reactions

Ervin Kovács, Balázs Huszka, Tamás Gáti, Miklós Nyerges, F. Faigl, Zoltán Mucsi

Research output: Contribution to journalArticle

Abstract

The present study reports regio- and highly diastereoselective preparative methods for the synthesis of versatile alkaloid-type compounds from oxiranylmethyl tetrahydroisoquinolines. 2,5-Methanobenzo[c]azepines or azetidine-fused heterocycles were synthesized in tandem reactions depending on the absence or presence of a BF3 co-reagent. A high functional group tolerance has also been demonstrated. DFT calculations with an explicit solvent model confirmed the proposed reaction mechanisms and the role of kinetic controls on the stereochemical outcome of the reported new methods.

Original languageEnglish
Pages (from-to)7100-7112
Number of pages13
JournalJournal of Organic Chemistry
Volume84
Issue number11
DOIs
Publication statusPublished - Jun 7 2019

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Azepines
Tetrahydroisoquinolines
Alkaloids
Discrete Fourier transforms
Functional groups
Kinetics
azetidine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Chemoselective Strategy for the Direct Formation of Tetrahydro-2,5-methanobenzo[c]azepines or Azetotetrahydroisoquinolines via Regio- and Stereoselective Reactions. / Kovács, Ervin; Huszka, Balázs; Gáti, Tamás; Nyerges, Miklós; Faigl, F.; Mucsi, Zoltán.

In: Journal of Organic Chemistry, Vol. 84, No. 11, 07.06.2019, p. 7100-7112.

Research output: Contribution to journalArticle

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