Midya Siba Prasad, Gopi Elumalai, Satam Nishikant, Namboothiri Irishi N N
Department of Chemistry Indian Institute of Technology, Bombay, Mumbai 400 076, India.
Org Biomol Chem. 2017 May 3;15(17):3616-3627. doi: 10.1039/c7ob00529f.
Addition of N-ylides derived from DABCO to chalconimines takes place through a Michael addition-cyclization pathway to afford fused cyanopyrroles and/or spirocyclopropanes. The product profile depends heavily on the nature of chalconimines. While 6-membered cyclic chalconimines provide a mixture of pyrrole and spirocyclopropane, 5-membered chalconimines furnish exclusively spirocyclopropane. Cyclopropane was the only product in the case of a representative open chain chalconimine as well. On the other hand, chalcones provide only spirocyclopropanes which is in contrast to the previously reported reactivity of enones. The complementary nature of the reactivity of the tetralone derived chalcone and its corresponding imine in providing spirocyclopropane and pyrrole, respectively, has also been demonstrated.
将源自1,4 - 二氮杂双环[2.2.2]辛烷（DABCO）的叶立德添加到查尔酮亚胺上，通过迈克尔加成 - 环化途径进行，以得到稠合氰基吡咯和/或螺环丙烷。产物分布很大程度上取决于查尔酮亚胺的性质。虽然六元环查尔酮亚胺提供吡咯和螺环丙烷的混合物，但五元查尔酮亚胺仅提供螺环丙烷。在代表性的开链查尔酮亚胺的情况下，环丙烷也是唯一的产物。另一方面，查尔酮仅提供螺环丙烷，这与之前报道的烯酮的反应性形成对比。也已证明四氢萘酮衍生的查尔酮及其相应亚胺在分别提供螺环丙烷和吡咯方面反应性的互补性质。
