INFLUENCE OF BICYCLIC ANHYDRIDE STRUCTURE ON THE OUTCOME OF THE CASTAGNOLI–CUSHMAN REACTION

Authors

  • Oleh K. Smyrnov Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601, Ukraine
  • Mykhailo I. Adamovskyi Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601, Ukraine
  • Tetiana V. Druzhenko Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601, Ukraine
  • Kostiantyn P. Melnykov Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601, Ukraine
  • Dmitriy M. Volochnyuk Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601, Ukraine Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02660, Ukraine
  • Sergey V. Ryabukhin Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01601, Ukraine Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02660, Ukraine

DOI:

https://doi.org/10.1007/7650

Keywords:

anhydrides, imines, Castagnoli–Cushman reaction, conformational restriction, multicomponent reactions.

Abstract

The Castagnoli–Cushman reaction was carried out with various fused and bridged bicyclic anhydrides. The influence of the anhydride nature and, specifically, the size of fused anhydride rings on the reaction pathway were investigated. The negative outcome of the reaction in the case of small rings and bridged systems was mechanistically described. The scope and limitations of the procedure involving anhydrides and imines were discussed. The high diastereoselectivity of the method was proved and showed its correlation with the previous results. The reaction was optimized and scaled up to afford multigram amounts of products in a single run (up to 50 g).

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Published

2023-08-09

Issue

Vol. 59 No. 6/7 (2023): Ukrainian impact on heterocyclic chemistry after the three decades of independence

Section

Original Papers