Regioselective Reactions of Ethyl (4,5-Dihydrofuran-3-yl)-2-oxoacetate and Ethyl 2-(3,4-Dihydro-2H-pyran-6-yl)-2-oxoacetate with 1-Unsubstituted Aminoazoles

The reactions of ethyl (4,5-dihydrofuran-3-yl)-2-oxoacetate and ethyl 2-(3,4-dihydro-2H-pyran-6-yl)-2-oxoacetate, as 1,3-bielectrophiles, with N-unsubstituted 5-aminoazoles, as N-C-N-binucleophiles, are the subject of this work. Regioselective heterocyclizations of ethyl 2-(3,4-dihydro-2H-pyran-6-yl...

Full description

Saved in:
Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 44; no. 6; pp. 895 - 902
Main Authors Stepaniuk, Oleksandr O., Matvienko, Vitalii O., Kondratov, Ivan S., Shishkin, Oleg V., Volochnyuk, Dmitriy M., Mykhailiuk, Pavel K., Tolmachev, Andrei A.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.03.2012
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CONVENIENT SYNTHESIS
pyrazolo[1,5-a]pyrimidines
SERIES
SRC KINASE INHIBITORS
ONE-POT SYNTHESIS
aminoazoles
RECEPTOR
DISCOVERY
lactones
AFFINITY
triazolo[1,5-a]pyrimidines
BIOLOGICAL EVALUATION
heterocyclization
DERIVATIVES
HALOACETYLATED ENOL ETHERS
Online AccessGet more information

Cover

More Information
Summary:The reactions of ethyl (4,5-dihydrofuran-3-yl)-2-oxoacetate and ethyl 2-(3,4-dihydro-2H-pyran-6-yl)-2-oxoacetate, as 1,3-bielectrophiles, with N-unsubstituted 5-aminoazoles, as N-C-N-binucleophiles, are the subject of this work. Regioselective heterocyclizations of ethyl 2-(3,4-dihydro-2H-pyran-6-yl)-2-oxoacetate lead to 3-hydroxypropyl-7-ethoxycarbonyl substituted pyrazolo-[1,5-a]pyrimidines and triazolo[1,5-a] pyrimidines whilst the corresponding reactions of ethyl (4,5-dihydrofuran-3-yl)-2-oxoacetate result in the formation of oxodihydropyrano[4,3-e] annulated products.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0031-1289733