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Highly stereoselective construction of spiro[cyclopropane-1,4′-pyrazolin-5′-one]with 4-arylidene-3-methyl-1-phenyl-pyrazolin-5-one and arsonium ylide |
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| Authors: | Zhongjiao Ren Weiguo Cao Jie Chen Hongmei Deng Danyi Wu |
| Institution: | a Department of Chemistry, Shanghai University, Shanghai 200444, China b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032, China c Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, China |
| Abstract: | A highly stereoselective synthesis of exo-spirocyclopropane-1,4′-pyrazolin-5′-one] from 4-arylidene-3-methyl-1-phenyl-pyrazolin-5-one and arsonium bromide in the presence of base has been achieved. The triphenylarsine-catalyzed cyclopropanation of 4-arylidene-3-methyl-1-phenyl-pyrazolin-5-one with bromide in the presence of NaHCO3 has also been studied. Both exo and endo isomers were formed in this reaction. The structures of the products were characterized by IR, MS, 1H NMR, elemental analysis, and X-ray diffraction analysis. |
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