5-Aryloxazolidines as Reagents for Double Alkylation of Arenes: A Novel Synthesis of 4-Aryltetrahydroisoquinolines
Publication type: Journal Article
Publication date: 2021-09-30
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
34591479
Organic Chemistry
Abstract
5-Aryloxazolidines react with arenes under Lewis or Brønsted acid conditions via the Friedel-Crafts/Pictet-Spengler double alkylation sequence to give alkaloid-like 4-aryltetrahydroisoquinolines in 12-94% yields. Three approaches for the controlled insertion of substituents into the target molecules and application of oxazolidine derivatives such as 1-arylethanol-2-amines or 4-hydroxytetrahydroisoquinolines in the alkylation of arenes are also described. An unprecedented two-step easily scalable synthesis of the 4-aryltetrahydroisoquinoline core from aromatic aldehyde was achieved applying oxazolidine methodology.
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Citations from 2024:
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Buev E. M. et al. 5-Aryloxazolidines as Reagents for Double Alkylation of Arenes: A Novel Synthesis of 4-Aryltetrahydroisoquinolines // Journal of Organic Chemistry. 2021. Vol. 86. No. 21. pp. 15307-15317.
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Buev E. M., Smorodina A. A., Moshkin V. S., Sosnovskikh V. Y. 5-Aryloxazolidines as Reagents for Double Alkylation of Arenes: A Novel Synthesis of 4-Aryltetrahydroisoquinolines // Journal of Organic Chemistry. 2021. Vol. 86. No. 21. pp. 15307-15317.
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TY - JOUR
DO - 10.1021/acs.joc.1c01881
UR - https://doi.org/10.1021/acs.joc.1c01881
TI - 5-Aryloxazolidines as Reagents for Double Alkylation of Arenes: A Novel Synthesis of 4-Aryltetrahydroisoquinolines
T2 - Journal of Organic Chemistry
AU - Buev, Evgeny M
AU - Smorodina, Anastasia A
AU - Moshkin, Vladimir S
AU - Sosnovskikh, Vyacheslav Ya.
PY - 2021
DA - 2021/09/30
PB - American Chemical Society (ACS)
SP - 15307-15317
IS - 21
VL - 86
PMID - 34591479
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2021_Buev,
author = {Evgeny M Buev and Anastasia A Smorodina and Vladimir S Moshkin and Vyacheslav Ya. Sosnovskikh},
title = {5-Aryloxazolidines as Reagents for Double Alkylation of Arenes: A Novel Synthesis of 4-Aryltetrahydroisoquinolines},
journal = {Journal of Organic Chemistry},
year = {2021},
volume = {86},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/acs.joc.1c01881},
number = {21},
pages = {15307--15317},
doi = {10.1021/acs.joc.1c01881}
}
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MLA
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Buev, Evgeny M., et al. “5-Aryloxazolidines as Reagents for Double Alkylation of Arenes: A Novel Synthesis of 4-Aryltetrahydroisoquinolines.” Journal of Organic Chemistry, vol. 86, no. 21, Sep. 2021, pp. 15307-15317. https://doi.org/10.1021/acs.joc.1c01881.