Work

Application of 1,4-Oxazinone Precursors to the Construction of Pyridine Derivatives by Tandem Intermolecular Cycloaddition/Cycloreversion

Year: 2021

Type: article

Abstract: This study reveals a new method for the preparation of 1,4-oxazinone derivatives by Staudinger reductive cyclization of functionalized vinyl azide precursors. The resulting oxazinone derivatives prepared in this manner were intercepted with terminal alkyne substrates through an intermolecular cycloaddition/cycloreversion sequence to afford polysubstituted pyridine products. Alkyne substrates bearing propargyl oxygen substitution showed good regioselectivity in the cycloaddition operation selectively affording 2,4,6-substituted pyridines. Application of this chemistry to the synthesis of an ErbB4 receptor inhibitor is also described.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.1c00288

Authors: Nicole A. Carrillo Vallejo, Jonathan R. Scheerer

Institution: William & Mary

Language: English

Topic: Organic Chemistry Cycloaddition Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Arnold and Mabel Beckman Foundation, National Institute of General Medical Sciences

Award: New methods to prepare 1,4-oxazin-2-ones and applications in the construction of polysubstituted pyridines