Synthesis of Isoquinolines via the [4+2] Cycloaddition Reaction of Oxazoles and Arynes

Author(s)

Silva, Tamiris R. C. ; Souza, Vinicius V. ; Raminelli, Cristiano

• Document type: Journal article
• Source: CHEMISTRYSELECT; v. 7, n. 33, p. 4-pg., 2022-09-06.

Abstract

Herein, we report our investigations on the reaction of a variety of substituted oxazoles with o-(trimethylsilyl)aryl triflates promoted by potassium fluoride and 18-crown-6-ether. Several functionalized isoquinoline compounds were obtained in moderate to good yields when the transformation was carried out at room temperature, followed by acidic workup, presumably via a [4+2] cycloaddition-ring-opening reaction pathway. Alternatively, bicyclic ethers were produced in reasonable yields when performing the transformation at 60 degrees C via a sequence of [4+2] cycloaddition, retro-Diels-Alder, and [4+2] cycloaddition reactions. (AU)

• FAPESP's process: 20/12530-8 - 2-(Trimethylsilyl)aryl trifluoromethanesulfonates as aryne precursors aiming to the preparation of functionalized (hetero)aromatic compounds and syntheses of bioactive natural products
• Grantee: Cristiano Raminelli
• Support Opportunities: Regular Research Grants