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Updated: Jul 19, 2025
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Intramolecular cyclization of N-cyano sulfoximines by N-CN bond activation
Ye Ji Seo1,2, Eunsil Kim1,3, In Seok Oh1,3
1Department of Drug Discovery, Korea Research Institute of Chemical Technology (KRICT) 141 Gajeong-ro, Yuseong-gu Daejeon 34114 Republic of Korea sjunpark@krict.re.kr +82 42 860 7160 +82 42 860 7175.
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.
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