Organic compounds containing N-O bonds exhibit an unmatched diversity of chemical properties and reactivities. The importance of nitroxy compounds is evidenced by their extensive use in the synthesis of advanced synthetic intermediates, chemical dyes, functional materials, agrochemicals and pharmaceuticals. However, pluripotent reactivities of compounds containing N-O bonds very often lead to low chemo-, regio- and stereoselectivities, which in turn have adversely affected the progress in the development of catalytic stereo- and regioselective approaches in heterocyclic synthesis.We have developed a host of new reactions that allow for facile synthesis of a variety of N-heterocycles from compounds containing N-O bonds. Thus, oxazines can be accessed by means of a catalytic hetero-Diels-Alder reaction. Another useful 1,2-oxazine synthesis that has been developed in our laboratory allows for a concise total synthesis of several oxazine natural products. Furthermore, 2-substituted azines can be prepared from N-oxides via a copper-catalyzed reaction with Grignard reagents.

New methods of heterocyclic synthesis based on reactions of nitroxy compounds

248th National Meeting (2014)

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