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An Investigation of the Diels-Alder Cycloadditions of 2(H)-1,4-Oxazin-2-ones.

By Kamyar Afarinkia, A. Bahar, M.J. Bearpark, J. Garcia-Ramos, A. Ruggiero, J. Neuse and M. Vyas

Abstract

NoForumla chem. . A variety of 5-chloro-2(H)-1,4-oxazin-2-ones bearing a range of substituents at their 3- and 6-positions undergo Diels-Alder cycloaddition as a 2-azadiene component with electron-rich, electron-deficient, and electron-neutral dienophiles. These reactions proceed with moderate regio- and stereoselectivity to afford relatively stable and readily isolable bridged bicyclic lactone cycloadducts. Chemical manipulation of these cycloadducts affords highly substituted and functionally rich piperidines. The regio- and stereochemical preferences of the cycloadditions of 5-chloro-2(H)-1,4-oxazin-2-ones are investigated computationally using density functional theory (B3LYP/6-31G*)

Topics: Oxygen nitrogen heterocycle, Nitrogen heterocycle, Oxygen heterocycle, Ketone, Oxazine derivatives, Density functional method, Stereochemistry, Piperidine derivatives, Lactone, Diels Alder addition, Stereoselectivity, Regioselectivity
Year: 2005
DOI identifier: 10.1021/jo051646i
OAI identifier: oai:bradscholars.brad.ac.uk:10454/3750
Provided by: Bradford Scholars
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