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Tunable Approach to Diverse Phenethylamines via Reduction of 5-Aryloxazolidines with Triethylsilane. / Smorodina, Anastasia; Buev, Evgeny; Moshkin, Vladimir et al.
In: Journal of Organic Chemistry, Vol. 89, No. 4, 16.02.2024, p. 2294-2305.

Research output: Contribution to journal › Article › peer-review

Harvard

Smorodina, A, Buev, E, Moshkin, V & Sosnovskikh, V 2024, 'Tunable Approach to Diverse Phenethylamines via Reduction of 5-Aryloxazolidines with Triethylsilane', Journal of Organic Chemistry, vol. 89, no. 4, pp. 2294-2305. https://doi.org/10.1021/acs.joc.3c02264

APA

Smorodina, A., Buev, E., Moshkin, V., & Sosnovskikh, V. (2024). Tunable Approach to Diverse Phenethylamines via Reduction of 5-Aryloxazolidines with Triethylsilane. Journal of Organic Chemistry, 89(4), 2294-2305. https://doi.org/10.1021/acs.joc.3c02264

Vancouver

Smorodina A, Buev E, Moshkin V, Sosnovskikh V. Tunable Approach to Diverse Phenethylamines via Reduction of 5-Aryloxazolidines with Triethylsilane. Journal of Organic Chemistry. 2024 Feb 16;89(4):2294-2305. doi: 10.1021/acs.joc.3c02264

Author

Smorodina, Anastasia ; Buev, Evgeny ; Moshkin, Vladimir et al. / Tunable Approach to Diverse Phenethylamines via Reduction of 5-Aryloxazolidines with Triethylsilane. In: Journal of Organic Chemistry. 2024 ; Vol. 89, No. 4. pp. 2294-2305.

BibTeX

@article{19e5946b86584cf3bfcbe23bd3ca9e4c,
title = "Tunable Approach to Diverse Phenethylamines via Reduction of 5-Aryloxazolidines with Triethylsilane",
abstract = "A rapid pathway for the synthesis of various β-phenethylamines from aromatic aldehydes has been developed. Initially, a wide range of 5-aryloxazolidines was prepared via the [3 + 2] cycloaddition reaction of N-methylazomethine ylide derived from sarcosine and paraformaldehyde. The subsequent reduction of 5-aryloxazolidines with triethylsilane in trifluoroacetic acid yields three types of products: N,N-dimethylphenylethanolamines, N,N-dimethylphenethylamines, and tetrahydroisoquinolines, depending on the substituents in the aromatic ring and reaction conditions. Moreover, an additional step of oxazolidine hydrolysis or ring-opening with hydrogen cyanide allowed us to synthesize N-methyl- or N-methyl-N-(cyanomethyl)phenethylamines.",
author = "Anastasia Smorodina and Evgeny Buev and Vladimir Moshkin and Vyacheslav Sosnovskikh",
note = "This work was financially supported by the Russian Science Foundation (Grant 22-73-10008).",
year = "2024",
month = feb,
day = "16",
doi = "10.1021/acs.joc.3c02264",
language = "English",
volume = "89",
pages = "2294--2305",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "4",

}

RIS

TY - JOUR

T1 - Tunable Approach to Diverse Phenethylamines via Reduction of 5-Aryloxazolidines with Triethylsilane

AU - Smorodina, Anastasia

AU - Buev, Evgeny

AU - Moshkin, Vladimir

AU - Sosnovskikh, Vyacheslav

N1 - This work was financially supported by the Russian Science Foundation (Grant 22-73-10008).

PY - 2024/2/16

Y1 - 2024/2/16

N2 - A rapid pathway for the synthesis of various β-phenethylamines from aromatic aldehydes has been developed. Initially, a wide range of 5-aryloxazolidines was prepared via the [3 + 2] cycloaddition reaction of N-methylazomethine ylide derived from sarcosine and paraformaldehyde. The subsequent reduction of 5-aryloxazolidines with triethylsilane in trifluoroacetic acid yields three types of products: N,N-dimethylphenylethanolamines, N,N-dimethylphenethylamines, and tetrahydroisoquinolines, depending on the substituents in the aromatic ring and reaction conditions. Moreover, an additional step of oxazolidine hydrolysis or ring-opening with hydrogen cyanide allowed us to synthesize N-methyl- or N-methyl-N-(cyanomethyl)phenethylamines.

AB - A rapid pathway for the synthesis of various β-phenethylamines from aromatic aldehydes has been developed. Initially, a wide range of 5-aryloxazolidines was prepared via the [3 + 2] cycloaddition reaction of N-methylazomethine ylide derived from sarcosine and paraformaldehyde. The subsequent reduction of 5-aryloxazolidines with triethylsilane in trifluoroacetic acid yields three types of products: N,N-dimethylphenylethanolamines, N,N-dimethylphenethylamines, and tetrahydroisoquinolines, depending on the substituents in the aromatic ring and reaction conditions. Moreover, an additional step of oxazolidine hydrolysis or ring-opening with hydrogen cyanide allowed us to synthesize N-methyl- or N-methyl-N-(cyanomethyl)phenethylamines.

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85184806287

UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=001163382700001

U2 - 10.1021/acs.joc.3c02264

DO - 10.1021/acs.joc.3c02264

M3 - Article

VL - 89

SP - 2294

EP - 2305

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 4

ER -

ID: 53749794