Novel Convenient Approach to 6-, 7-, and 8-Numbered Nitrogen Heterocycles Incorporating Endocyclic Sulfonamide Fragment

Authors :: Eduard B. Rusanov
Oleksandr O. Shalimov
Oksana V. Muzychka
Petro P. Onys’ko
Source :: Molecules, Volume 25, Issue 12, Molecules, Vol 25, Iss 2887, p 2887 (2020)
Publication Year :: 2020
Publisher :: MDPI, 2020.
Abstract: 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<br />N&ndash<br />S reagent with benzylamines that act as 1,4-N&ndash<br />C&ndash<br />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.

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