Facile synthesis of spirosubstituted cyclopropanes through reaction of electron-deficient olefins and 1, 3-indandione. Issue 4 (23rd January 2020)

• Record Type: Journal Article
• Authors: Huang, Jiamin; Liu, Wenli; Wang, Changqing; Yang, Liu; Cao, Xiaohua
• Is Part Of: Tetrahedron letters. Volume 61:Issue 4(2020)
• Publication Date: 2020-01-23
• Subjects: Spirocyclopropyl compound -- 1, 3-Indandione -- Iodine -- Alkenes; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.151417
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Facile synthesis of spirocyclopropanes by 1, 3-indandione and arylidenemalononitrile. The reaction occurred in the presence of molecular iodine and dimethylaminopyridine. Various substituents on the benzene ring were well tolerated and gave good yields. The structures of products were confirmed by NMR and X-ray diffraction analysis. A possible mechanism of this reaction process is proposed. Abstract: An efficient and facile approach for the synthesis of spirosubstituted cyclopropane derivatives has been described. The reaction of 1, 3-indandione with arylidenemalononitrile in the presence of molecular iodine and dimethylaminopyridine occurred to give cyclopropanes in moderate to excellent yields. The structures of the products were characterized by NMR and X-ray diffraction analysis. A possible mechanism of this reaction process is proposed.