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Highly Active Cyclic Zinc(II) Thione Catalyst for C−C and C−N Bond Formation Reactions

Von Wiley-VCH zur Verfügung gestellt

First discrete mononuclear zinc(II) thione catalyzed Knoevenagel condensation reactions, and 2,3-dihydroperimidine synthesis are reported with the best catalytic activities.


Abstract

The first discrete seven-membered cyclic zinc(II) complex catalyzed room temperature Knoevenagel condensation reactions, and the synthesis of perimidine derivatives has been reported under mild reaction conditions. The cyclic zinc(II) complex [(L)ZnBr2] (1) was isolated from the reaction between 1-(2-hydroxyethyl)-3-isopropyl-benzimidazol-2-thione (L) and ZnBr2. Complex 1 was characterized by different analytic techniques such as FT-IR, CHNS, TGA, NMR, and SCXRD. The mononuclear zinc(II) complex 1 was utilized as a catalyst for Knoevenagel condensation reactions to isolate twenty different substituted methylene malononitriles with excellent yield. Besides, the zinc(II) thione complex 1 was utilized for the synthesis of 2,4-dihydroperimidine derivatives in a highly efficient manner. Catalyst 1 depicted wide substrate scopes. Overall, twenty different substituted methylene malononitriles and nine different perimidine derivatives were synthesized using catalyst 1 at room temperature. The present investigation features a mild and fast synthetic approach along with excellent functional group tolerance.

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