A Tandem Ring Opening/Closure Reaction in A BF3‐Mediated Rearrangement of Spirooxindoles. Issue 24 (16th October 2017)

• Record Type: Journal Article
• Authors: Guo, Xuliang; Xing, Qingyu; Lei, Kunhua; Zhang‐Negrerie, Daisy; Du, Yunfei; Zhao, Kang
• Is Part Of: Advanced synthesis & catalysis. Volume 359:Issue 24(2017)
• Page Start: 4393
• Page End: 4398
• Publication Date: 2017-10-16
• Subjects: Spirocyclohexadienones -- BF3 -- 8-hydroxy-phenanthridin-6(5H)-one -- ring opening; ring closure; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201700728
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Treatment of the readily accessible spiro‐cyclohexadienones from the PhI(OCOCF3 )2 ‐mediated spiro‐cyclization of N‐substituted benzanilides, with BF3 ⋅Et2 O initiates a tandem ring opening/closure reaction leading to the formation of the biologically interesting 8‐hydroxy‐phenanthridin‐6(5 H )‐one compounds. This unique rearrangement pattern involves the 'migration' of the electron‐deficient N ‐methyl carbamoyl moiety rather than the electron‐rich aryl group as observed and reported previously in all other similar transformations. Abstract :