A Divergent Nickel-Catalyzed Synthesis of Quinazolinediones and Benzoxazinone Imines

William Wertjes; Sloan Ayers; Qi Gao; Eric M. Simmons; Gregory L. Beutner

doi:10.1055/s-0037-1610140

Synthesis, Table of Contents

Synthesis 2018; 50(22): 4453-4461
DOI: 10.1055/s-0037-1610140

paper

A Divergent Nickel-Catalyzed Synthesis of Quinazolinediones and Benzoxazinone Imines

William Wertjes

^aChemical and Synthetic Development, Bristol-Myers Squibb Company, One Squibb Drive, New Brunswick, NJ 08903-0191, U.S.A. Email: gregory.beutner@bms.com

,

Sloan Ayers

^aChemical and Synthetic Development, Bristol-Myers Squibb Company, One Squibb Drive, New Brunswick, NJ 08903-0191, U.S.A. Email: gregory.beutner@bms.com

,

Qi Gao

^bDrug Product Sciences and Technology, Bristol-Myers Squibb Company, One Squibb Drive, New Brunswick, NJ 08903-0191, U.S.A.

,

Eric M. Simmons

^aChemical and Synthetic Development, Bristol-Myers Squibb Company, One Squibb Drive, New Brunswick, NJ 08903-0191, U.S.A. Email: gregory.beutner@bms.com

,

Gregory L. Beutner *

^aChemical and Synthetic Development, Bristol-Myers Squibb Company, One Squibb Drive, New Brunswick, NJ 08903-0191, U.S.A. Email: gregory.beutner@bms.com

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Abstract

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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 65^th 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.

Key words

quinazolinedione - benzoxazinone - nickel - cycloaddition

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References

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Supplementary Material

Supporting Information