Cycliaddition Reactions Of Polysubstituted Cyclopropanes

Cyclopropanes have found a wide range of applications in modern organic synthesis. And it has drawn significant attentions of the chemists over the past decade. Introduction of various functional groups into the cyclopropane ring extends its reactivity significantly. They react with both nucleophiles and electrophiles. However, the most interesting synthetic application of Donor-Acceptor cyclopropanes is related to their ability to react, under Lewis acid or organic bases mediated conditions to afford five or six-membered carbo-and heterocycles.Here, we process a series of experiments of polysubstituted cyclopropanes mediated by organic bases undergoing a variety of reactions. And we’ve achieved a series of meaningful experimental results.1.We use a series of cyclopropanes (2-(4-Nitro-phenyl)-3-aryl-cyclopropane-1,1-dicarbonitrile and1-Cyano-2-(4-nitro-phenyl)-3-aryl-cyclopropanecarboxylic acid ethyl ester) to act as reactants in a Gewald Reaction. Under the condition given in the references, the reaction successfully yielded fourteen2-Amino-5-(4-nitro-phenyl)-4-phenyl-thiophene-3-carbonitrile derivatives. We Screened reaction conditions to select the optimal reaction conditions. The reaction results have been characterized by NMR, IR, HRMS and X-Ray.2. We use a series of cyclopropanes (2-Benzoyl-3-aryl-cyclopropane-1,1-dicarbonitrile and1-Cyano-2-benzoyl-3-aryl-cyclopropanecarboxylic acid ethyl ester) to act as reactants in a Gewald Reaction. Under the condition given in the references,the reaction successfully yielded tweleve2-Amino-thiophene derivatives. We screened reaction conditions to select the optimal reaction conditions. The reaction results have been characterized by NMR, IR, HRMS and X-Ray.3. There are references of Donor-acceptor cyclopropanes undergoing a variety of self isomerization and dimerization. We carried on a dimerization reaction of2-Benzoyl-3-aryl-cyclopropane-1,1-dicarbonitrile. We obtained thirteen dimers. The reaction conditions were optimized. And the products were characterized by NMR, IR, HRMS and X-Ray.