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Intramolecular cyclization of N-cyano sulfoximines by N-CN bond activation.

ABSTRACT: Metal-free halogenated anhydrides promote the intramolecular cyclization of N-cyano sulfoximines. Trifluoro- or trichloroacetic anhydride (TFAA or TCAA, respectively) activate the N-cyano groups of N-cyano sulfoximines, leading to the intramolecular cyclization of 2-benzamide-N-cyano sulfoximines 1. This method results in excellent yields of thiadiazinone 1-oxides 2. A full intramolecular cyclization pattern was suggested by (i) labeling experiments with ¹³C, (ii) isolating of N-trifluoroacetyl sulfoximine 1ac, and (iii) confirming the generation of the intermediate 1ad by LC/MS analysis.

SUBMITTER: Seo YJ

PROVIDER: S-EPMC10424563 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature

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Intramolecular cyclization of N-cyano sulfoximines by N-CN bond activation.

Seo Ye Ji YJ Kim Eunsil E Oh In Seok IS Hyun Ji Young JY Song Ji Ho JH Lim Hwan Jung HJ Park Seong Jun SJ

RSC advances 20230814 35

Metal-free halogenated anhydrides promote the intramolecular cyclization of N-cyano sulfoximines. Trifluoro- or trichloroacetic anhydride (TFAA or TCAA, respectively) activate the N-cyano groups of N-cyano sulfoximines, leading to the intramolecular cyclization of 2-benzamide-N-cyano sulfoximines 1. This method results in excellent yields of thiadiazinone 1-oxides 2. A full intramolecular cyclization pattern was suggested by (i) labeling experiments with 13 ...[more]

PMID: 37583669

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