Multistep Continuous Flow Synthesis of Isolable NH2 -Sulfinamidines via Nucleophilic Addition to Transient Sulfurdiimide.
Chemistry
; 28(59): e202202066, 2022 Oct 21.
Article
em En
| MEDLINE
| ID: mdl-35861934
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 NH2 -sulfinamidines by nucleophilic attack of organometallic reagents to inâ
situ prepared N-(trimethylsilyl)-N-trityl-λ4 -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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Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Brometos
/
Lítio
Idioma:
En
Revista:
Chemistry
Assunto da revista:
QUIMICA
Ano de publicação:
2022
Tipo de documento:
Article
País de afiliação:
Itália