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 Vol. 13; no. 35; pp. 24445 - 24449 |
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Main Authors | , , , , , , |
Format | Journal Article |
Published |
14.08.2023
|
Online Access | Get full text |
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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. |
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Bibliography: | Electronic supplementary information (ESI) available. CCDC For ESI and crystallographic data in CIF or other electronic format see DOI 2271515 https://doi.org/10.1039/d3ra04208a |
ISSN: | 2046-2069 |
DOI: | 10.1039/d3ra04208a |