Synthesis 2018; 50(22): 4453-4461
DOI: 10.1055/s-0037-1610140
paper
© Georg Thieme Verlag Stuttgart · New York

A Divergent Nickel-Catalyzed Synthesis of Quinazolinediones and Benzoxazinone Imines

William Wertjes
a  Chemical 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
a  Chemical 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
b  Drug Product Sciences and Technology, Bristol-Myers Squibb Company, One Squibb Drive, New Brunswick, NJ 08903-0191, U.S.A.
,
Eric M. Simmons
a  Chemical and Synthetic Development, Bristol-Myers Squibb Company, One Squibb Drive, New Brunswick, NJ 08903-0191, U.S.A.   Email: gregory.beutner@bms.com
,
a  Chemical and Synthetic Development, Bristol-Myers Squibb Company, One Squibb Drive, New Brunswick, NJ 08903-0191, U.S.A.   Email: gregory.beutner@bms.com
› Author Affiliations
Further Information

Publication History

Received: 21 March 2018

Accepted after revision: 09 April 2018

Publication Date:
17 May 2018 (eFirst)

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

 
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