HFIP‐Mediated Decarboxylative [4+3]‐Annulation of Azaoxyallyl Cations with Isatoic Anhydride. Issue 17 (29th May 2020)

• Record Type: Journal Article
• Authors: Kim, Eunjin; Lee, Chang Yoon; Kim, Sung‐Gon
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 17(2020)
• Page Start: 3594
• Page End: 3603
• Publication Date: 2020-05-29
• Subjects: Benzodiazepinedione -- Annulation -- Decarboxylative addition -- Azaoxyallyl cation -- Isatoic anhydride; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202000439
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: The first example of a [4+3]‐annulation reaction between in situ‐generated azaoxyallyl cations and isatoic anhydride has been developed for the construction of seven‐membered 1, 4‐benzodiazepinediones in moderate to good yields (up to 91% yield). This annulation reaction involves the cascade reaction of decarboxylative addition of hexafluoroisopropanol to isatoic anhydride, addition to the azaoxyallyl cation, and intramolecular substitution to yield 1, 4‐benzodiazepinediones. Abstract :