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Julia C. Reisenbauer, Ori Green, Allegra Franchino, Patrick Finkelstein, Bill Morandi
Advances in the field of late-stage functionalization have expedited lead-structure discovery and established new opportunities to access valuable molecules. Although many peripheral late-stage transformations, mainly focusing on C–H functionalizations, have been reported, reliable strategies to directly edit the core skeleton of lead compounds have remained scarce. Late-stage remodeling strategies of widely encountered and pharmaceutically relevant scaffolds, such as indoles, would offer enormous potential to expand accessible chemical space. Herein, we report the skeletal editing of indoles through nitrogen atom insertion, accessing their corresponding quinazoline or quinoxaline bioisosteres via trapping of an electrophilic nitrene species generated from ammonium carbamate and hypervalent iodine. This unique reactivity is unlocked through the strategic use of a silyl group which acts as a reactivity-controlling element to suppress the inherent nucleophilicity of the nitrogen in indoles. Importantly, the utility of this highly functional group-tolerant methodology in the context of late-stage skeletal editing of several commercial drugs is demonstrated.
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Reisenbauer, J. C., Green, O., Franchino, A., Finkelstein, P., & Morandi, B. (2022). Late-stage diversification of indole skeletons through nitrogen atom insertion. Science, 377(6610), 1104–1109. https://doi.org/10.1126/science.add1383
Reisenbauer, Julia C., et al. "Late-stage diversification of indole skeletons through nitrogen atom insertion." Science, vol. 377, no. 6610, 2022, pp. 1104–1109, https://doi.org/10.1126/science.add1383.
Reisenbauer, Julia C., Ori Green, Allegra Franchino, Patrick Finkelstein, and Bill Morandi. "Late-stage diversification of indole skeletons through nitrogen atom insertion." Science 377, no. 6610 (2022): 1104–1109. https://doi.org/10.1126/science.add1383.
Reisenbauer J. C., Green O., Franchino A. [и др.] Late-stage diversification of indole skeletons through nitrogen atom insertion // Science. — 2022. — Vol. 377, № 6610. — P. 1104–1109. — URL: https://doi.org/10.1126/science.add1383
@article{reisenbauer2022latestage,
title = {{Late-stage diversification of indole skeletons through nitrogen atom insertion}},
author = {Julia C. Reisenbauer and Ori Green and Allegra Franchino and Patrick Finkelstein and Bill Morandi},
journal = {Science},
year = {2022},
volume = {377},
number = {6610},
pages = {1104--1109},
doi = {10.1126/science.add1383},
url = {https://doi.org/10.1126/science.add1383}
}TY - JOUR AU - Reisenbauer, Julia C. AU - Green, Ori AU - Franchino, Allegra AU - Finkelstein, Patrick AU - Morandi, Bill TI - Late-stage diversification of indole skeletons through nitrogen atom insertion JO - Science VL - 377 IS - 6610 SP - 1104 EP - 1109 PY - 2022 DA - 2022/09/01 DO - 10.1126/science.add1383 UR - https://doi.org/10.1126/science.add1383 ER -
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