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. - V. 54, l. 20. - P. 2455-2457.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

Benzaldehydes with electron-donating substituents react smoothly with a nonstabilized azomethine ylide derived from sarcosine and formaldehyde to form 5-aryloxazolidines as intermediates, which undergo rearrangement into 2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ols in high yields by simple heating with hydrochloric acid. This one-pot synthesis of tetrahydroisoquinolines can be considered as a formal {[}3+3] cycloaddition of the azomethine ylide to the aromatic aldehyde. (C) 2013 Elsevier Ltd. All rights reserved.

Author keywords:

1,2,3,4-Tetrahydroisoquinolin-4-ols; 5-Aryloxazolidines; Nonstabilized azomethine ylide; {[}3+2] Cycloaddition; Rearrangement; Pictet-Spengler reaction AZOMETHINE YLIDE; ASYMMETRIC-SYNTHESIS; CACTUS ALKALOIDS; PHENETHYLAMINES; DERIVATIVES

DOI:

10.1016/j.tetlet.2013.02.087

Web of Science ID:

ISI:000317809900003

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAY 15
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	AZOMETHINE YLIDE; ASYMMETRIC-SYNTHESIS; CACTUS ALKALOIDS; PHENETHYLAMINES; DERIVATIVES
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	This work was supported financially by the RFBR (Grant 12-03-31036).
Number-of-Cited-References	35
Usage-Count-Since-2013	8
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	129AD