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

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 sulfoximin...

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Published in:RSC advances 2023-08, Vol.13 (35), p.24445-24449
Main Authors: Seo, Ye Ji, Kim, Eunsil, Oh, In Seok, Hyun, Ji Young, Song, Ji Ho, Lim, Hwan Jung, Park, Seong Jun
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Summary: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 C, (ii) isolating of N -trifluoroacetyl sulfoximine 1ac , and (iii) confirming the generation of the intermediate 1ad by LC/MS analysis. Metal-free halogenated anhydrides promote the intramolecular cyclization of N -cyano sulfoximines. This method results in excellent yields of thiadiazinone 1-oxides.
ISSN:2046-2069
DOI:10.1039/d3ra04208a