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  • 1
    ISSN: 0170-2041
    Keywords: 6H-1,2-Oxazines ; Methoxyallene ; Nitroso alkene ; Hetero Diels-Alder reaction ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Regioselective hetero Diels-Alder reactions of in-situ generated nitroso alkenes 2-4 with methoxyallene derivatives 1 provide 4H-1,2-oxazines 5-7 with an exo-methylene group at C-5. These primary cycloadducts are smoothly transformed into conjugated 6H-1,2-oxazines 11-13 by base or acid catalysis. The bicylic nitroso alkene 17 and methoxyallene (1a) combine to give the tricyclic 1,2-oxazine 18, thus demonstrating that an exo-transition state is favoured in this [4+2] cycloaddition. The reaction of the sterically hindered methoxyallene 1h with nitrosostyrene affords the cycloadduct 22 in low yield. 22 is very likely formed by a two-step Diels-Alder reaction via a zwitterion. Allene derivatives lacking a methoxy group are not sufficiently reactive towards nitroso alkenes and do not provide 1,2-oxazines.
    Additional Material: 8 Tab.
    Type of Medium: Electronic Resource
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