Double C-N bond cleavages of N-alkyl 4-oxopiperidinium salts: access to unsymmetrical tertiary sulfonamides
| Autor: | Ming-Peng Li, Ying Fu, Chun-Zhao Shi, Zhengyin Du, Fang-Rong Li, Congde Huo |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Sulfonyl 010405 organic chemistry Organic Chemistry Salt (chemistry) 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Sulfonamide Homolysis Metal chemistry visual_art visual_art.visual_art_medium Amine gas treating Physical and Theoretical Chemistry Alkyl |
| Zdroj: | Organicbiomolecular chemistry. 17(48) |
| ISSN: | 1477-0539 |
| Popis: | In this paper, regiospecific, double intraannular C–N bond cleavages of N-alkyl 4-oxopiperidinium salts are presented. The reaction sequence involves a charge-transfer complex, in situ formed between sulfonyl chloride and N-methylmorpholine, which induces S–Cl bond homolysis of sulfonyl chloride, yielding a reactive sulfonyl radical that further induces the double C–N bond cleavages of N-alkyl 4-oxopiperidinium salt. The secondary amine thus produced was trapped by sulfonyl chloride to yield the desired sulfonamide product. The key feature of this protocol is that two intraannular C–N bonds of the 4-oxopiperidine ring are cleaved in one step under metal- and oxidant-free conditions. |
| Databáze: | OpenAIRE |
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