TY - JOUR
T1 - Shining light on tryptamine-derived isocyanides
T2 - access to constrained spirocylic scaffolds
AU - Wu, Minghui
AU - Saya, Jordy M.
AU - Han, Peiliang
AU - Walia, Rajat
AU - Pradhan, Bapi
AU - Honing, Maarten
AU - Ranjan, Prabhat
AU - Orru, Romano V. A.
PY - 2024/5/14
Y1 - 2024/5/14
N2 - 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. © 2024 The Royal Society of Chemistry
AB - 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. © 2024 The Royal Society of Chemistry
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U2 - 10.1039/d3sc06304f
DO - 10.1039/d3sc06304f
M3 - RGC 21 - Publication in refereed journal
C2 - 38725510
SN - 2041-6520
VL - 15
SP - 6867
EP - 6873
JO - Chemical Science
JF - Chemical Science
IS - 18
ER -