Synthesis of Tetra‐Substituted Trifluoromethyl‐3, 1‐Benzoxazines by Transition‐Metal‐Catalyzed Decarboxylative Cyclization of N‐Benzoyl Benzoxazinones. Issue 5 (19th February 2021)

• Record Type: Journal Article
• Authors: Uno, Hiroto; Fujimoto, Daichi; Harada, Kyosuke; Tanaka, Chika; Shibata, Norio
• Is Part Of: ChemistryOpen. Volume 10:Issue 5(2021)
• Page Start: 518
• Page End: 522
• Publication Date: 2021-02-19
• Subjects: Benzoxazinones -- copper -- decarboxylation reactions -- fluorinated compounds -- heterocycle derivatives -- intramolecular cyclization reactions; Chemistry -- Periodicals; 540; 540.5
• DOI: 10.1002/open.202000360
• Languages: English
• ISSNs: 2191-1363

Abstract

Abstract: Efficient synthesis of N, O ‐heterocyclic tetra‐substituted trifluoromethyl‐3, 1‐benzoxazines via a transition‐metal‐catalyzed decarboxylative intramolecular cyclization was achieved. The decarboxylation of N ‐benzoyl trifluoromethyl‐benzoxazinones generated the amide oxygen nucleophile, allowing a selective internal C1 ‐attack on Pd‐ or Cu‐coordinated zwitterions, affording medicinally attractive tetra‐substituted vinyl‐ or ethynyl‐trifluoromethyl‐3, 1‐benzoxazines. This protocol can be applied to the synthesis of perfluoroalkyl‐ and non‐fluorinated 3, 1‐benzoxazines. Abstract : Efficient synthesis of N, O‐ heterocyclic tetra‐substituted trifluoromethyl‐3, 1‐benzoxazines via a transition‐metal‐catalyzed decarboxylative intramolecular cyclization was achieved. The decarboxylation of N‐benzoyl trifluoromethyl‐benzoxazinones generated the amide oxygen nucleophile, allowing a selective internal C1 ‐attack on Pd‐ or Cu‐coordinated zwitterions, affording medicinally attractive tetra‐substituted vinyl‐ or ethynyl‐trifluoromethyl‐3, 1‐benzoxazines. This protocol can be applied to the synthesis of perfluoroalkyl‐ and non‐fluorinated 3, 1‐benzoxazines.