Результаты исследований: Вклад в журнал › Статья › Рецензирование
Результаты исследований: Вклад в журнал › Статья › Рецензирование
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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