Synthesis And Cycloaddition Reactions Of 2,3,4,5Tetrahydropyrazine
1-Oxide
Wazeer, MIM; Perzanowski, HP; Qureshi, SI; Al-Murad, MB; Ali, SA
PERGAMON-ELSEVIER SCIENCE LTD, TETRAHEDRON; pp: 7229-7236; Vol: 56
King Fahd University of Petroleum & Minerals
http://www.kfupm.edu.sa
Summary
The stereochemistry and reactivity of the cycloaddition reactions of a heterocyclic
nitrone, 2,3,4,5,-tetrahydropyrazine I-oxide, have been studied. The heterocyclic
nitrone is found to be more reactive than its carbocyclic counterpart. The nitrone
underwent regio- and stereo-selective cycloaddition reaction with several alkenes to
afford bicyclic isoxazolidines efficiently. Barriers to nitrogen inversion in the
cycloadducts have been determined. (C) 2000 Elsevier Science Ltd. ALI rights
reserved.
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