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. - V. 54, l. 44. - P. 5869-5872.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

Benzaldehydes react smoothly with nonstabilized azomethine ylides, generated in situ from sarcosine/ formaldehyde or N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine, to give 5-aryloxazolidines as intermediates. These were converted into 2-(alkylamino)-1-arylethanols in good yields by simple heating in methanol with hydrochloric acid, or by treatment with hydrazine hydrate in ethanol. (C) 2013 Elsevier Ltd. All rights reserved.

Author keywords:

Benzaldehydes; Nonstabilized azomethine ylides; {[}3+2] Cycloaddition; 5-Aryloxazolidines; Phenethylamines; Epinephrine (adrenaline) AZOMETHINE YLIDES; 1,3-DIPOLAR CYCLOADDITION; 3-SUBSTITUTED COUMARINS; CACTUS ALKALOIDS

DOI:

10.1016/j.tetlet.2013.08.083

Web of Science ID:

ISI:000325666500008

Соавторы в МНС:

Другие поля

Поле	Значение
Month	OCT 30
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	AZOMETHINE YLIDES; 1,3-DIPOLAR CYCLOADDITION; 3-SUBSTITUTED COUMARINS; CACTUS ALKALOIDS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	mvslc@mail.ru
ResearcherID-Numbers	Moshkin, Vladimir/E-6623-2017
Funding-Acknowledgement	RFBR {[}12-03-31036]
Funding-Text	The research was carried out under the terms of the Ural Federal University development program with the financial support of young scientists, and was supported financially by RFBR (Grant 12-03-31036).
Number-of-Cited-References	37
Usage-Count-Last-180-days	3
Usage-Count-Since-2013	14
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	234TF