Domino aza/oxa-hetero-Diels–Alder reaction for construction of novel spiro[pyrido[3′,2′:5,6]pyrano[2,3-d]pyrimidine-7,5′-pyrimidine]

Abstract

The unprecedented reaction of α,β-unsaturated N-arylaldimines with two molecular 5-arylidene-1,3-dimethylbarbituric acids in methylene dichloride at room temperature afforded unique spiro[pyrido[3′,2′:5,6]pyrano[2,3-d]pyrimidine-7,5′-pyrimidines] in moderate to good yields and with high diastereoselectivity. The reaction was believed to proceed with domino aza/oxa-hetero-Diels–Alder reactions, in which the two substrates not only acted as active aza-/oxa-1,4-dienes, but also played as reactive dienophiles.