DOI: 10.1002/slct.74049 ISSN: 2365-6549
(3+3)‐Cycloaddition‐Based Synthesis of Spirocyclic 1,2‐Oxazinanes Fused With Imidazol‐4‐One
Amir M. Al Mufti, Kirill D. Kungurtsev, Airat I. Kashapov, Alexander A. Korlyukov, Alexander A. Romanenko, Pavel N. Solyev, Viktoria A. Ikonnikova, Mohammad Nurul Azmi, Mikhail S. Baranov, Andrey A. MikhaylovABSTRACT
(3+3)‐Cycloaddition provides a reliable approach to create spirocycles. A new 1,2‐oxazine‐based scaffold is available via acid‐promoted reaction of imidazole‐4‐one activated donor‐acceptor cyclopropanes with nitrones. The performed detailed study of the reactivity of nitrones of various types reveal the main regularities of the process. A highly diastereoselective reaction is observed for N‐ methyl nitrones, derived from electron‐deficient benzaldehydes.