Intramolecular Buchwald-Hartwig N-Arylation of Bicyclic Hydrazines: Practical Access to Spiro[indoline-2,3'-piperidines]

16 December 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

In recent years, spirocycles have been the focus of medicinal chemistry, and several drugs or drug candidates incorporating these “non-planar” chemical motifs have been developed. New advancements in this field, however, are greatly limited by the lack of innovative methods enabling the preparation of original spirocyclic cores. Here-in, an unprecedented intramolecular Buchwald-Hartwig N-arylation of bicyclic hydrazines is described. This key reaction gives access to unique spiro[indoline-2,3'-piperidine] derivatives after reductive cleavage of the nitro-gen–nitrogen bond. This approach widens the chemical space of spirocycles and may reveal useful to explore new avenues of research in drug discovery.

Keywords

spiro compounds
bicyclic hydrazines
diamino-piperidines
indolines
Buchwald-Hartwig couplings

Supplementary materials

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Description
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Supporting Information
Description
Synthetic procedures for the preparation of all products; characterization data; copies of 1H NMR and 13C NMR spectra
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