Synthesis 2012(6): 895-902  
DOI: 10.1055/s-0031-1289733
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Oleksandr O. Stepaniuka,b, Vitalii O. Matvienkoa,b, Ivan S. Kondratov*b,c, Oleg V. Shishkind, Dmitriy M. Volochnyukb,e, Pavel K. Mykhailiuka,b, Andrei A. Tolmacheva,b
a Kyiv National Taras Shevchenko University, 64 Volodymirska st., 01033 Kiev-33, Ukraine
b Enamine Ltd., 23 A. Matrosova st., 01103 Kiev, Ukraine
Fax: +380(44)5373253; e-Mail: vanya_ko@mail.ru;
c Institute of Bioorganic Chemistry and Petrochemistry, National Ukrainian Academy of Science, Murmanska 1, 02660 Kiev-94, Ukraine
d STC Institute for Single Crystals, NAS of Ukraine, 60 Lenina ave., 61001 Kharkiv, Ukraine
e Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, 02094 Kiev-94, Ukraine
Further Information

Publication History

Received 9 December 2011
Publication Date:
01 March 2012 (eFirst)

Abstract

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.