Nonstabilized azomethine ylides as reagents for alkylaminomethylation of aromatic ketones via 5-aryloxazolidines

被引：20

作者：

Moshkin, Vladimir S. ^{[1
]}

Buev, Evgeny M. ^{[1
]}

Sosnovskikh, Vyacheslav Y. ^{[1
]}

机构：

[1] Ural Fed Univ, Inst Nat Sci, Dept Chem, Ekaterinburg 620000, Russia

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 38期

基金：

俄罗斯科学基金会;

关键词：

Carbonyl compounds; Nonstabilized azomethine ylides; 3+2] Cycloaddition; 5-Aryloxazolidines; 2-Amino-1-arylethanols; ONE-POT SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; CACTUS ALKALOIDS; ALCOHOLS; DECARBOXYLATION; DERIVATIVES; ALDEHYDES; SARCOSINE;

D O I：

10.1016/j.tetlet.2015.07.068

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aromatic ketones were found to react smoothly with nonstabilized azomethine ylides, generated in situ from sarcosine/formaldehyde or N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine, to give 5-aryloxazolidines which were converted into 2-alkylaminoethanols in moderate to good yields by heating in n-butanol with hydrochloric acid. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：5278 / 5281

页数：4

共 34 条

[1] Reagents for Storage and Regeneration of Nonstabilized Azomethine Ylides: Spiroanthraceneoxazolidines
Buev, Evgeny M.
Moshkin, Vladimir S.
Sosnovskikh, Vyacheslav Y.
ORGANIC LETTERS, 2016, 18 (08) : 1764 - 1767
[2] Synthesis of 5-aryloxazolidines via 1,3-dipolar cycloaddition reaction of a non-stabilized azomethine ylide with aromatic aldehydes
Ryan, John H.
Spiccia, Nadia
Wong, Leon S. -M.
Holmes, Andrew B.
AUSTRALIAN JOURNAL OF CHEMISTRY, 2007, 60 (12) : 898 - 904
[3] 5-Aryloxazolidines as Reagents for Double Alkylation of Arenes: A Novel Synthesis of 4-Aryltetrahydroisoquinolines
Buev, Evgeny M.
Smorodina, Anastasia A.
Moshkin, Vladimir S.
Sosnovskikh, Vyacheslav Y.
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (21): : 15307 - 15317
[4] Tunable Approach to Diverse Phenethylamines via Reduction of 5-Aryloxazolidines with Triethylsilane
Smorodina, Anastasia A.
Buev, Evgeny M.
Moshkin, Vladimir S.
Sosnovskikh, Vyacheslav Y.
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (04): : 2294 - 2305
[5] Transmutation of 1,3-dipoles. The conversion of α-diazo ketones into azomethine ylides via carbonyl ylides
1600, (114):
[6] A simple two-step synthesis of 2-(alkylamino)-1-arylethanols, including racemic adrenaline, from aromatic aldehydes via 5-aryloxazolidines
Moshkin, Vladimir S.
Sosnovskikh, Vyacheslav Ya.
TETRAHEDRON LETTERS, 2013, 54 (44) : 5869 - 5872
[7] Synthesis of benzopyranopyrrolidines via 1,3-dipolar cycloaddition of nonstabilized azomethine ylides with 3-substituted coumarins
Moshkin, Vladimir S.
Sosnovskikh, Vyacheslav Ya.
Roeschenthaler, Gerd-Volker
TETRAHEDRON, 2013, 69 (29) : 5884 - 5892
[8] TRANSMUTATION OF 1,3-DIPOLES - THE CONVERSION OF ALPHA-DIAZO KETONES INTO AZOMETHINE YLIDES VIA CARBONYL YLIDES
PADWA, A
DEAN, DC
ZHI, L
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (02) : 593 - 601
[9] A one-pot synthesis of tetrahydroisoquinolin-4-ols via a novel acid-catalyzed rearrangement of 5-aryloxazolidines
Moshkin, Vladimir S.
Sosnovskikh, Vyacheslav Ya.
TETRAHEDRON LETTERS, 2013, 54 (20) : 2455 - 2457
[10] SIMPLE GENERATION OF NONSTABILIZED AZOMETHINE YLIDES THROUGH DECARBOXYLATIVE CONDENSATION OF ALPHA-AMINO-ACIDS WITH CARBONYL-COMPOUNDS VIA 5-OXAZOLIDINONE INTERMEDIATES
TSUGE, O
KANEMASA, S
OHE, M
TAKENAKA, S
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (11) : 4079 - 4089

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