Novel Convenient Approach to 6-, 7-, and 8-Numbered Nitrogen Heterocycles Incorporating Endocyclic Sulfonamide Fragment
| Autor: | Eduard B. Rusanov, Oleksandr O. Shalimov, Oksana V. Muzychka, Petro P. Onys’ko |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Nitrogen
Molecular Conformation Pharmaceutical Science chemistry.chemical_element Medicinal chemistry Article Analytical Chemistry lcsh:QD241-441 chemistry.chemical_compound imidoyl chlorides 1 2 4-thiadiazocines lcsh:Organic chemistry N S-heterocyclic S S-dioxides Group (periodic table) Heterocyclic Compounds Drug Discovery Lewis acids and bases Physical and Theoretical Chemistry electrophilic heterocyclization 1 2 4-thiadiazines 1 2 4-thiadiazepines chemistry.chemical_classification Sulfonamides Imidoyl chloride Chemistry Organic Chemistry Sulfonamide Chemistry (miscellaneous) Cyclization Reagent Electrophile Molecular Medicine Pharmacophore |
| Zdroj: | Molecules Volume 25 Issue 12 Molecules, Vol 25, Iss 2887, p 2887 (2020) |
| ISSN: | 1420-3049 |
| Popis: | A new effective method for the construction of nitrogen heterocycles incorporating endocyclic pharmacophore sulfonamide fragment, based on the use of easy accessible N-(chlorosulfonyl)imidoyl chloride, CCl3C(Cl)=NSO2Cl (1), has been developed. Thus, a reaction of 1 as bielectrophilic 1,3-C&ndash N&ndash S reagent with benzylamines that act as 1,4-N&ndash C&ndash C-C binucleophiles, affords respective 1,2,4-benzothiadiazepine-1,1-dioxides. On the other hand, 1 reacts with alkenyl amines with the formation of respective N-alkenyl amidines undergoing Lewis acids initiated intramolecular cyclization to afford derivatives of 1,2,4-thiadiazines and 1,2,4-thiadiazocines bearing a halomethyl group able for further functionalization. The first examples of electrophilic heterocyclization of the chlorosulfonyl group onto an alkenyl or alkynyl group have been revealed. |
| Databáze: | OpenAIRE |
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