Approach to 3-aminoindolin-2-ones via oxime ether functionalized carbamoylcyclohexadienes

The Journal of Organic Chemistry
A Franco BellaJohn C Walton

Abstract

O-Benzyloxime ether substituted amidocyclohexadienes were prepared in three steps in good yields from 2-aminoacetophenone. EPR spectroscopic observations and product analyses showed that peroxide-induced decompositions of model compounds led to indolin-2-ones with benzyloxyaminyl substitution at their 3-positions. The cyclization steps were very rapid and took place regioselectively at the C-atoms of the C=N bonds, by 5-exo ring closures. An O-trityloxime ether analogue was also prepared. The cyclohexadienyl intermediate smoothly yielded an alkoxylaminyl radical again by rapid 5-exo-cyclization. However, ring closure was quickly followed by another beta-scission step that released the persistent trityl radical and a 3-nitrosoindolin-2-one derivative. EPR spectroscopic evidence showed that the nitroso compound trapped other transient intermediates to afford a series of nitroxides. GC-MS analyses of products formed in reactions including methyl thioglycolate indicated that 1-benzyl-3-methyl-1,3-dihydro-2H-indol-2-one was derived from the indolinone moiety.

References

May 8, 2003·Journal of the American Chemical Society·Armido StuderJohn C Walton

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Citations

Jul 7, 2005·Angewandte Chemie·Jens Kemper, Armido Studer
Mar 21, 2012·Organic & Biomolecular Chemistry·Feng ZhouJian Zhou
Aug 28, 2009·Organic Letters·Liang ChengYong-Jun Chen
Jun 7, 2008·Organic Letters·Stephen P MarsdenSteven A Raw
Aug 30, 2008·The Journal of Organic Chemistry·Edouard GodineauYannick Landais
Oct 20, 2005·Accounts of Chemical Research·John C Walton, Armido Studer
Apr 1, 2015·Organic Letters·Benjamin OvadiaYannick Landais
Feb 8, 2007·Journal of the American Chemical Society·Derrick L J CliveRajendra Subedi

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