Synthesis and nucleophilic properties of 1-(2-methoxyethyl) and 1-(2-phenoxyethyl)-3,3-dialkyl-3,4-dihydroisoquinolines

A. G. Mikhailovskii; Михайловский Александр Георгиевич; A. S. Yusov; Юсов Алексей Сергеевич; N. N. Pershina; Першина Наталья Николаевна

doi:10.31857/S0514749224040062

Synthesis and nucleophilic properties of 1-(2-methoxyethyl) and 1-(2-phenoxyethyl)-3,3-dialkyl-3,4-dihydroisoquinolines

Authors: Mikhailovskii A.G.¹, Yusov A.S.¹, Pershina N.N.¹
Affiliations:
1. Perm State Pharmaceutical Academy
Issue: Vol 60, No 4 (2024)
Pages: 461-467
Section: Articles
URL: https://rjpbr.com/0514-7492/article/view/672162
DOI: https://doi.org/10.31857/S0514749224040062
EDN: https://elibrary.ru/RZCJAD
ID: 672162

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Abstract

The Ritter reaction of dialkyl benzyl carbinols with 3-methoxy- and 3-phenoxypropanenitriles afforded the corresponding 1-(2-methoxyethyl)- and 1-(2-phenoxyethyl)-3,3-dialkyl-3,4-dihydroisoquinolines. Likewise, benzo[f]isoquinoline derivatives were synthesized from 2-methyl-3-(naphthalen-1-yl)propan-2-ol. The obtained compounds were shown to have the imine structure, but they exhibited enamine properties. In particular, their reactions with oxalyl chloride resulted in pyrrole annulation.

Keywords

β-methoxy and β-phenoxy-propionitriles, Ritter cyclocondensation, 1-(2-methoxyethyl) and 1-(2-phenoxyethyl)-3,3-dialkyl-3,4-dihydroisoquinolines, enamines, oxalyl chloride, annelation of the pyrrole cycle

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About the authors

A. G. Mikhailovskii

Perm State Pharmaceutical Academy

Author for correspondence.
Email: neorghim@pfa.ru
ORCID iD: 0000-0002-5104-4877
Russian Federation, ul. Polevaya, 2, Perm, 614990

A. S. Yusov

Perm State Pharmaceutical Academy

Email: neorghim@pfa.ru
ORCID iD: 0000-0003-4059-2613
Russian Federation, ul. Polevaya, 2, Perm, 614990

N. N. Pershina

Perm State Pharmaceutical Academy

Email: neorghim@pfa.ru
ORCID iD: 0000-0002-1422-2902
Russian Federation, ul. Polevaya, 2, Perm, 614990

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