4.4 Article

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

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CHEMISTRYSELECT
卷 7, 期 33, 页码 -

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/slct.202203039

关键词

Benzyne chemistry; Bicyclic ethers; Cycloaddition; Heterocycles; Isoquinolines

资金

  1. Sao Paulo Research Foundation (FAPESP) [2020/12530-8]
  2. National Council for Scientific and Technological Development (CNPq)
  3. Coordination for the Improvement of Higher Education Personnel (CAPES)

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In this study, we investigated the reaction of several substituted oxazoles with o-(trimethylsilyl)aryl triflates promoted by potassium fluoride and 18-crown-6-ether. We obtained functionalized isoquinoline compounds in moderate to good yields at room temperature through a [4+2] cycloaddition-ring-opening reaction pathway, followed by acidic workup. Alternatively, bicyclic ethers were produced in reasonable yields at 60 degrees C through a sequence of [4+2] cycloaddition, retro-Diels-Alder, and [4+2] cycloaddition reactions.
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.

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