Study Of Multicomponent Reactions Participated By Acetylenedicarboxyaltes

Multicomponent reactions (MCRs) means three or more of the starting material introduced into the reaction with one-pot procedure to generate a final product, the main parts of all the segments of materials were combined into the structure of final product. It involves the reactions of two or more functional groups in the process, or it can be regarded as a combination of multiple double molecule reaction. However, multicomponent reaction is not only a simple superposition of several normal double-molecular reaction, but also the organic combination of sequential reactions according to the domino rules. In this article, we have successfully developed several multicomponent reactions by employing acetylenedicarboxylates to synthesize a series of nitrogen-containing heterocyclic compounds. These reactions have the advantages of using common starting material, mild reaction conditions and operational simplicity. It has provided a feasible and effective method for the synthesis of diverse nitrogen-containing heterocyclic compounds.1. The four-component reactions of arylamines, dialkyl acetylenedicarboxylates, acenaphthenequinone and dimedone (or cyclohexane-1,3-dione) in acetic acid provided an efficient synthetic procedure for the functionalized spiro[acenaphthylene-1,2'-quinoline] derivatives in good yields. Totally,25 new spiro compounds were obtained in good yields and were fully characterized by IR, NMR and HRMS spectroscopy. The single crystal structures of two prepared compounds were determined by X-ray diffraction method.2. The one-pot two-step reactions of 4-picoline, dialkyl acetylenedicarboxylates and 2-oxoindolin-3-ylidene derivatives in DME at elevated temperature afforded polyfunctionalized 2-(1-(2-oxoindolin-3-ylidene)-2-aryl-2-oxoethyl)fumarates in moderate to good yields. The reaction mechanism involves the sequential formation of Huisgen' 1,4-dipole, Michael addition and splitting off pyridyl moiety. The 10 compounds were characterized by IR, NMR and HRMS spectroscopy. The single crystal structures of two prepared compounds were determined by X-ray diffraction method.3. The synthetic method of one important medical intermediate SATA was investigated, A optimized reaction conditions were obtained by examining reaction solvent, temperature, and catalysts in the reaction. Comparing with the reported method, this procedure has the advantages of short reaction time and higher yield.