Shining light on tryptamine-derived isocyanides: access to constrained spirocylic scaffolds.

Dearomatization of indoles through a charge transfer complex constitutes a powerful tool for synthesizing three-dimensional constrained structures. However, the implementation of this strategy for the dearomatization of tryptamine-derived isocyanides to generate spirocyclic scaffolds remains underdeveloped. In this work, we have demonstrated the ability of tryptamine-derived isocyanides to form aggregates at higher concentration, enabling a single electron transfer step to generate carbon-based-radical intermediates. Optical, HRMS and computational studies have elucidated key aspects associated with the photophysical properties of tryptamine-derived isocyanides. The developed protocol is operationally simple, robust and demonstrates a novel approach to generate conformationally constrained spirocyclic scaffolds, compounds with high demand in various fields, including drug discovery. This journal is © The Royal Society of Chemistry.

Citation

Minghui Wu, Jordy M Saya, Peiliang Han, Rajat Walia, Bapi Pradhan, Maarten Honing, Prabhat Ranjan, Romano V A Orru. Shining light on tryptamine-derived isocyanides: access to constrained spirocylic scaffolds. Chemical science. 2024 May 08;15(18):6867-6873

PMID: 38725510

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