Synthesis of Vinylcyclopropane‐Fused Pyrazolone Derivatives by Sulfur Ylide‐Initiated 1, 6‐Michael Addition‐Cyclization Reactions. Issue 34 (23rd August 2018)

• Record Type: Journal Article
• Authors: Li, Xiang; Liu, Yan‐Qing; Kang, Jing‐Wen; Chen, Fei‐Yu; He, Xi‐Guo; Yuan, Shan‐Shan; Guo, Li; Peng, Cheng; Huang, Wei
• Is Part Of: European journal of organic chemistry. Issue 34(2018)
• Page Start: 4723
• Page End: 4730
• Publication Date: 2018-08-23
• Subjects: Sulfur -- Ylides -- Cyclization -- Heterocycles -- Pyrazolone; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201800710
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A highly diastereoselective cyclopropanation of α, β, γ, δ‐unsaturated pyrazolones has been disclosed. This method allows for construction of a vinylcyclopropane‐fused pyrazolone framework via a 1, 6‐addition/substitution sequence providing excellent regio‐ and chemoselectivity, good yields, broad functional group tolerance and gram‐scale capacity. Moreover, the subsequent transformation of derivatives demonstrates great potential in building useful synthetic architectures. Abstract : A highly diastereoselective cyclopropanation of α, β, γ, δ‐unsaturated pyrazolones is reported. This method affords a vinylcyclopropane‐fused pyrazolone framework by a 1, 6‐addition/substitution sequence providing excellent regio‐ and chemoselectivity, good yields, broad functional group tolerance and gram‐scale capacity.