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

; 
Bahar, A.
; 
Bearpark, M.J.
; 
Garcia-Ramos, J.
; 
Ruggiero, A.
; 
Neuse, J.
; 
Vyas, M.
Publication Date
2005
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Keywords
Oxygen nitrogen heterocycle, Nitrogen heterocycle, Oxygen heterocycle, Ketone, Oxazine derivatives, Density functional method, Stereochemistry, Piperidine derivatives, Lactone, Diels Alder addition, Stereoselectivity, Regioselectivity
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Abstract
Forumla 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*).
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http://hdl.handle.net/10454/3750
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Citation
Afarinkia, K., Bahar, A., Bearpark, M.J. and Garcia-Ramos, J et al. (2005). An Investigation of the Diels-Alder Cycloadditions of 2(H)-1,4-Oxazin-2-ones. Journal of Organic Chemistry. Vol. 70, No. 23, pp. 9529-9537.
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https://doi.org/10.1021/jo051646i
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