Reagents for Storage and Regeneration of Nonstabilized Azomethine Ylides: Spiroanthraceneoxazolidines / Buev Evgeny M.,Moshkin Vladimir S.,Sosnovskikh Vyacheslav Y. // ORGANIC LETTERS. - 2016. - V. 18, l. 8. - P. 1764-1767.

ISSN/EISSN:

1523-7060 / 1523-7052

Type:

Article

Abstract:

Nonstabilized azomethine ylides are easily trapped by anthraquinone to form stable spiro-oxazolidines, which have an unusual ability to undergo a cycloreversion in the presence of other dipolarophiles at 120-150 degrees C. All tested recycloadditions with carbonyl compounds and electron-poor alkenes occurred in moderate to high yields (41-92\%). Moreover, increasing the reaction temperature to 210 degrees C made it possible to obtain adducts with low reactive dipolarophiles.

Author keywords:

FLASH VACUUM THERMOLYSIS; ALPHA-AMINO-ACIDS; 1,3-DIPOLAR CYCLOADDITION; STEREOSPECIFIC SYNTHESIS; 3-SUBSTITUTED COUMARINS; DECARBOXYLATIVE ROUTE; 2-AZAALLYL ANIONS; N-OXIDE; DERIVATIVES; 5-ARYLOXAZOLIDINES

DOI:

10.1021/acs.orglett.6b00475

Web of Science ID:

ISI:000374436800014

Соавторы в МНС:

Другие поля

Поле	Значение
Month	APR 15
Publisher	AMER CHEMICAL SOC
Address	1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Language	English
EISSN	1523-7052
Keywords-Plus	FLASH VACUUM THERMOLYSIS; ALPHA-AMINO-ACIDS; 1,3-DIPOLAR CYCLOADDITION; STEREOSPECIFIC SYNTHESIS; 3-SUBSTITUTED COUMARINS; DECARBOXYLATIVE ROUTE; 2-AZAALLYL ANIONS; N-OXIDE; DERIVATIVES; 5-ARYLOXAZOLIDINES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	mvslc@mail.ru
ResearcherID-Numbers	Moshkin, Vladimir/E-6623-2017
Funding-Acknowledgement	Russian Science Foundation {[}14-13-00388]
Funding-Text	This work was financially supported by the Russian Science Foundation (Grant 14-13-00388).
Number-of-Cited-References	49
Usage-Count-Last-180-days	4
Usage-Count-Since-2013	13
Journal-ISO	Org. Lett.
Doc-Delivery-Number	DJ8BJ