Reaction of 5-aryloxazolidines with arylmagnesium bromides as a new route to N-benzyl-beta-hydroxyphenethylamines as starting materials for the preparation of 4-aryl-1,2,3,4-tetrahydroisoquinolines / Moshkin Vladimir S.,Sosnovskikh Vyacheslav Ya. // TETRAHEDRON LETTERS. - 2013. - V. 54, l. 21. - P. 2699-2702.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

Benzaldehydes react smoothly with the non-stabilized azomethine ylide derived from sarcosine and formaldehyde to form 5-aryloxazolidines as intermediates, which undergo ring-opening to give N-benzyl-beta-hydroxyphenethylamines in good yields by the action of arylmagnesium bromides. Their subsequent acid-catalyzed cyclization into 4-aryl-1,2,3,4-tetrahydroisoquinolines was performed in moderate to good yields. (c) 2013 Elsevier Ltd. All rights reserved.

Author keywords:

4-Aryl-1,2,3,4-tetrahydroisoquinolines; 5-Aryloxazolidines; Non-stabilized azomethine ylide; {[}3+2] Cycloaddition; Cyclization reaction ONE-POT SYNTHESIS; DOPAMINE D-1; CHERYLLINE; TETRAHYDROISOQUINOLINES; (\&/-)-CHERYLLINE; REARRANGEMENT; DERIVATIVES; CYCLIZATION

DOI:

10.1016/j.tetlet.2013.03.076

Web of Science ID:

ISI:000318393000034

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAY 22
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	ONE-POT SYNTHESIS; DOPAMINE D-1; CHERYLLINE; TETRAHYDROISOQUINOLINES; (\&/-)-CHERYLLINE; REARRANGEMENT; DERIVATIVES; CYCLIZATION
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-Last-180-days	2
Usage-Count-Since-2013	10
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	136WB