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Synthesis of 1-substituted 4-ethoxycarbonyl-5- (ethoxycarbonylmethyl) pyrazoles Diethyl acetone-1, 3-dicarboxylate reacts with N, N-dimethylforma- mide dimethyl acetal (DMFDMA) in ethanol at room temperature. Unexpected product dichotomy is produced in the Biginelli-like condensation of 2-hydroxybenzaldehyde with urea or thiourea and dimethyl or diethyl acetone-1,3-dicarboxylate, respectively, as active methylene components. Ethyl 2-amino-4-(2-ethoxy-2-oxoethyl)thiazole-5-carboxylate (2a), prepared from diethylacetone-1,3-dicarboxylate, sulfuryl chloride and thiourea. Synthesis of diethyl 2,2-diethyl-3,5-dioxopimelate by the reaction of ethyl 3-chloro-3-oxo-2,2-dimethylpropionate with diethyl acetone-1,3-dicarboxylate.
T. A. Bryson,; T. M. Dolak. Dimethyl 2,3-Pentadienedioate. Organic Syntheses. <
Stefanie Reima,; Van Thi Hong Nguyen,; Uwe Albrechta,; Peter Langer. Synthesis of 3,5-dioxoalkanoates, 3,5-dioxopimelates and 2,4-dioxoadipates by acylation of 1,3-bis-silyl enol ethers. Tetrahedron Letters. 2005, 46 (48),8423-8425.
Valuable synthetic building block, compare Dimethyl acetone-1,3-dicarboxylate, A14969. Used in synthesis of isoquinolin-2-ones: Heterocycles, 33, 515 (1992).
Gefahrenhinweise (EU): H227
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