Diastereoselective and Efficient Synthesis of Indeno[2 '',1 '':4 ',5 ']furo[3 ',2 ':5,6]pyrido[2,3-d]pyrimidine-2,4,6(1H,3H)-trione and 6-(2,3-Dihydro-2-hydroxy-1,3-dioxo-1H-inden-2-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-2,4,7(1H,3H,6H)-trione Derivatives

摘要

A diastereoselective synthesis of some new N-containing heterocyclic compounds, indeno[2 '',1 '':4',5']furo[3',2':5,6]pyrido[2,3-d]pyrimidine-2,4,6(1H,3H)-trione derivatives, is presented. Products were obtained in good to excellent yields by the reaction of amino(thio)uracils with 2-hydroxy-2-(3-oxobut-1-en-2-yl)-2H-indene-1,3-dione in AcOH under reflux conditions. Also, a simple and efficient method was introduced for the synthesis of 6-(2,3-dihydro-2-hydroxy-1,3-dioxo-1H-inden-2-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-2,4,7(1H,3H,6H)-triones via the reaction of amino(thio)uracils and methyl 2-(2,3-dihydro-2-hydroxy-1,3-dioxo-1H-inden-2-yl)acrylate. The simple procedure and easy work-up, high yields, short reaction times, and diastereoselectivity of the reaction are salient features of this method. The structural assignments are supported by H-1- and C-13-NMR, and X-ray crystallography data.