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通过N-CN键活化实现的α-氰基磺胺亚胺的分子内环化反应。

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

作者信息

Seo Ye Ji, Kim Eunsil, Oh In Seok, Hyun Ji Young, Song Ji Ho, Lim Hwan Jung, Park Seong Jun

机构信息

Department of Drug Discovery, Korea Research Institute of Chemical Technology (KRICT) 141 Gajeong-ro, Yuseong-gu Daejeon 34114 Republic of Korea

Pharmaceutical Chemistry, University of Science & Technology Daejeon 34113 Republic of Korea.

出版信息

RSC Adv. 2023 Aug 14;13(35):24445-24449. doi: 10.1039/d3ra04208a. eCollection 2023 Aug 11.

DOI:10.1039/d3ra04208a
PMID:37583669
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10424563/
Abstract

Metal-free halogenated anhydrides promote the intramolecular cyclization of -cyano sulfoximines. Trifluoro- or trichloroacetic anhydride (TFAA or TCAA, respectively) activate the -cyano groups of -cyano sulfoximines, leading to the intramolecular cyclization of 2-benzamide--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 C, (ii) isolating of -trifluoroacetyl sulfoximine 1ac, and (iii) confirming the generation of the intermediate 1ad by LC/MS analysis.

摘要

无金属卤代酸酐促进氰基磺胺亚胺的分子内环化反应。三氟乙酸酐或三氯乙酸酐（分别为TFAA或TCAA）可活化氰基磺胺亚胺的氰基，从而导致2-苯甲酰胺基-氰基磺胺亚胺1发生分子内环化反应。该方法可得到高产率的噻二嗪酮1-氧化物2。通过以下几点表明了完整的分子内环化模式：（i）用碳进行标记实验；（ii）分离出α-三氟乙酰基磺胺亚胺1ac；（iii）通过液相色谱/质谱分析确认中间体1ad的生成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcbc/10424563/de00d4d0883b/d3ra04208a-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcbc/10424563/6500aca59762/d3ra04208a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcbc/10424563/34f457c764a5/d3ra04208a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcbc/10424563/942da3f310e9/d3ra04208a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcbc/10424563/9366c67e02ee/d3ra04208a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcbc/10424563/156594b256d2/d3ra04208a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcbc/10424563/de00d4d0883b/d3ra04208a-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcbc/10424563/6500aca59762/d3ra04208a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcbc/10424563/34f457c764a5/d3ra04208a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcbc/10424563/942da3f310e9/d3ra04208a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcbc/10424563/9366c67e02ee/d3ra04208a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcbc/10424563/156594b256d2/d3ra04208a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dcbc/10424563/de00d4d0883b/d3ra04208a-f4.jpg

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