Synthesis of podands with dihydropyrimidine fragments based on polyethers with terminal acetoacetamide groups / Radionova Elena S.,Fedorova Olga V.,Titova Yulia A.,Rusinov Gennady L.,Charushin Valery N. // CHEMISTRY OF HETEROCYCLIC COMPOUNDS. - 2015. - V. 51, l. 5. - P. 478-482.

ISSN/EISSN:

0009-3122 / 1573-8353

Type:

Article

Abstract:

Reactions of aliphatic aminopodands having different length of the polyether chain with acetoacetic ester and 2,2,6-trimethyl-4H-1,3-dioxin-4-one were studied. The interaction of aminopodands with acetoacetic ester in toluene upon sonication (60A degrees D) or heating (90A degrees D) gave podands with terminal aminocrotonate fragments. The use of dioxinone at the same temperature allowed to transform aminopodands into aliphatic acetoacetamide-containing podands. An asymmetric podand with 2-pyridone fragment was isolated as byproduct from the reaction of dioxinone with 1,5-diamino-3-oxapentane. A three-component Biginelli reaction of acetoacetamidecontaining podands with benzaldehyde and urea in the presence of catalytic amounts of polyphosphoric acid immobilized on nanosized TiO2-SiO2 oxide surface enabled the synthesis of podands with 1,4-dihydropyrimidin-2-(1De)-one fragments.

Author keywords:

acetoacetamide-containing podands; acetylketene; dihydropyrimidine-containing podands; nanosized oxide; polyphosphoric acid; Biginelli reaction POT MULTICOMPONENT SYNTHESIS; DIKETENE

DOI:

10.1007/s10593-015-1723-4

Web of Science ID:

ISI:000358138200010

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAY
Publisher	SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
EISSN	1573-8353
Keywords-Plus	POT MULTICOMPONENT SYNTHESIS; DIKETENE
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	sintonin@mail.ru fedorova@ios.uran.ru
Number-of-Cited-References	19
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	6
Journal-ISO	Chem. Heterocycl. Compds.
Doc-Delivery-Number	CN0XN