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  • The tert-Amino Effect in the Synthesis of Hetaryl- and Arylsulfonyl-Substituted Pyrrolo- and Pyrido[1,2-a]quinoline Derivatives and their Pyrazolo Annulated Analogues

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

Synthesis , 2012, 44 (06), 895-902

DOI: 10.1055/s-0031-1289733

Stepaniuk O. O.; Matvienko V. O.; Kondratov I. S.; Shishkin O. V.; Volochnyuk D. M.; Mykhailiuk P. K.; Tolmachev A. A.

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.

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

Stepaniuk O. O.; Matvienko V. O.; Kondratov I. S.; Shishkin O. V.; Volochnyuk D. M.; Mykhailiuk P. K.; Tolmachev A. A.
Synthesis 2012, 44 (06), 895-902
DOI: 10.1055/s-0031-1289733

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