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–N–S reagent with benzylamines that act as 1,4-N–C–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.
Highlights
Nitrogen heterocycles are part of a huge number of marketed drugs
Intermolecular addition of sulfonyl chlorides to olefins applied to unsaturated compounds with double or triple carbon‐carbon bond as nucleophilic site and under free-radical conditions is well documented and widely used sulfonyl chloride as electrophile
We believed that the reaction of N‐chlorosulfonyl imidoyl chloride 1 with one equivalent of an and the formation of respective unsaturated amidine, in which the location and polarity of sulfonyl unsaturated amine would result in regioselective substitution of the chlorine atom at the C=N bond chloride and olefinic fragment are favorable for intramolecular electrophilic heterocyclization
Summary
Nitrogen heterocycles are part of a huge number of marketed drugs. They are widely used in modern drugs design [1]. It can be concluded that synthetic benzothiadiazepines were synthetized byand cyclisation ofseven2-chlorosulfonylbenzoyl chloride with urea methods for the monocyclic thiadiazines especially for and eight numbered heterocycles with the endocyclic sulfonamide fragment are limited and rather specific for each particular and thiourea [22] These methods are limited by set of reagents, scope of reactions, andtype the of use of column compounds. We have developed aand convenient method the preparation of numbered novel C-N-S-heterocycles methods for theRecently, monocyclic thiadiazines especially forforsevenand eight bielectrophilic reagent, N-chlorosulfonyltrichloroacetimidoyl chloride 1a, and demonstrated its with the endocyclic sulfonamide fragment are limited and rather specific for each particular type of utility for the synthesis of 1,2,4-benzothiadiazine 1,1-dioxides derivatives [24] (Scheme 1).
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