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Synthesis 2018; 50(22): 4453-4461
DOI: 10.1055/s-0037-1610140
DOI: 10.1055/s-0037-1610140
paper
A Divergent Nickel-Catalyzed Synthesis of Quinazolinediones and Benzoxazinone Imines
Further Information
Publication History
Received: 21 March 2018
Accepted after revision: 09 April 2018
Publication Date:
17 May 2018 (online)
Dedicated to Prof. Scott Denmark on his birthday.
Published as part of the Special Section dedicated to Scott E. Denmark on the occasion of his 65th birthday
Abstract
During exploration of the nickel(0)-catalyzed reaction of isocyanates and isatoic anhydrides, it was found that changes in the substitution pattern of the isocyanate led to constitutionally isomeric quinazolinediones [quinazoline-2,4(1H,3H)-diones] or benzoxazinone imines [2-imino-1,2-dihydro-4H-3,1-benzoxazin-4-ones]. Ligand and solvent screening experiments allowed for identification of conditions that could lead to each constitutional isomer in good to excellent levels of selectivity and yield. Comprehensive characterization of the previously poorly characterized benzoxazinone imines is also provided.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610140.
- Supporting Information
-
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