Article Dans Une Revue Chemistry - A European Journal Année : 2022

Multistep Continuous Flow Synthesis of Isolable NH 2 ‐Sulfinamidines via Nucleophilic Addition to Transient Sulfurdiimide

Résumé

Abstract The growing interest in novel sulfur pharmacophores led to recent advances in the synthesis of some S(IV) and S(VI) motifs. However, preparation and isolation of uncommon primary sulfinamidines, the aza‐analogues of sulfinamides, is highly desirable. Here we report a multistep continuous flow synthesis of poorly explored NH 2 ‐sulfinamidines by nucleophilic attack of organometallic reagents to in situ prepared N ‐(trimethylsilyl)‐ N ‐trityl‐λ 4 ‐sulfanediimine (Tr−N=S=N−TMS). The transformation can additionally be realized under mild conditions, at room temperature, via a highly chemoselective halogen‐lithium exchange of aryl bromides and iodides with n ‐butyllithium. Moreover, the synthetic potential of the methodology was assessed by exploring further manipulations of the products and accessing novel S(IV) analogues of celecoxib, tasisulam, and relevant sulfinimidoylureas.

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hal-04413280 , version 1 (03-09-2024)

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Michael Andresini, Sébastien Carret, Leonardo Degennaro, Fulvio Ciriaco, Jean-François Poisson, et al.. Multistep Continuous Flow Synthesis of Isolable NH 2 ‐Sulfinamidines via Nucleophilic Addition to Transient Sulfurdiimide. Chemistry - A European Journal, 2022, 28 (59), ⟨10.1002/chem.202202066⟩. ⟨hal-04413280⟩
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