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Synthesis and Cycloaddition Reactions of 2,3,4,5-Tetrahydropyrazine 1-Oxide

✍ Scribed by Mohammed I.M Wazeer; Herman P Perzanowski; Sajid I Qureshi; Mohammad B Al-Murad; Sk Asrof Ali

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
201 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

The stereochemistry and reactivity of the cycloaddition reactions of a heterocyclic nitrone, 2,3,4,5,-tetrahydropyrazine 1-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.

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4,5-Dihydro-2-methyloxazole la and 4,5-dihydro-2,4.4-trimethyloxazole lb, which are examples of cyclic imidate esters, undergo 1,fdipolar cycloaddition reactions with benzonitrile N-oxide, to give the appropriate 5,6-dihydro-7a-methyl-3-