Synthesis of 6,12-Methanodibenzo[ c, f]azocines and 4-Aryltetrahydroisoquinolines from Aromatic Aldehydes

Evgeny M Buev; Maxim A Stepanov; Vladimir S Moshkin; Vyacheslav Y Sosnovskikh

doi:10.1021/acs.orglett.9b04401

Synthesis of 6,12-Methanodibenzo[ c, f]azocines and 4-Aryltetrahydroisoquinolines from Aromatic Aldehydes

Org Lett. 2020 Jan 17;22(2):631-635. doi: 10.1021/acs.orglett.9b04401. Epub 2019 Dec 31.

Authors

Evgeny M Buev¹, Maxim A Stepanov¹, Vladimir S Moshkin¹, Vyacheslav Y Sosnovskikh¹

Affiliation

¹ Institute of Natural Sciences and Mathematics , Ural Federal University , 620000 Ekaterinburg , Russian Federation.

PMID: 31891510
DOI: 10.1021/acs.orglett.9b04401

Abstract

A methodology for the synthesis of 7,12-dihydro-5H-6,12-methanodibenzo[c,f]azocines from aromatic aldehydes and N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine using catalysis by trifluoroacetic and perchloric acids is described. The developed protocol was applied for the synthesis of N-unsubstituted and N-methyl-4-aryltetrahydroisoquinolines.

Publication types

Research Support, Non-U.S. Gov't