ChemInform Abstract: Fluoro Containing Heterocycles. Part 1. Novel 1,4‐Benzothiazines and 1,2,4‐Benzothiadiazines.

Abstract

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Fluorinated azines and benzazines containing oxygen or sulfur atoms

“…Sulfamide 158 under reaction with triethyl orthoformate or diethyl oxalate undergoes the cyclization to give fluorinated 1,2,4-benzothiadiazines 159, 162 (Scheme 57) [111]. Interaction of 158 with acetic anhydride results in diacetyl derivative 160, which under reflux with pyperidine undergoes not only cyclization but also amino-defluorination process to give 161.…”

“…Another way to a variety of 1,4-benzothiazin-1,1-dioxides is described [111]. Chlorosulfonation of 3,4-difluoroaniline gave 2-amino-4,5-difluorobenzenesulfonyl chloride which was converted into the corresponding sodium sulfinate 119, which reacts with different bromocontaining ketones to give fluorinated 1,4-benzothiazin-1,1-dioxides 120-122 (Scheme 46).…”

“…Acid 148, derived from the ester 127 through the displacement of F 6 atom with Nmethylpiperazine and basic hydrolysis of the ethoxycarbonyl group, was subjected to biological trials as an inhibitor of DNA gyrase (Scheme 54) [112]. Alkylation of sulfone 122 with ethyl iodide in the presence K 2 CO 3 afforded compound 149 (Scheme 54) [111].…”

“…_ 3 ) T D $ F I G ] 3.4.2. Chemical properties 6,7-Difluoro-1,4-benzothiazin-1,1-dioxides 120-122 react with cycloalkylimines to give compounds 147 as a result of nucleophilic displacement of F 6 atom (Scheme 54) [111]. Acid 148, derived from the ester 127 through the displacement of F 6 atom with Nmethylpiperazine and basic hydrolysis of the ethoxycarbonyl group, was subjected to biological trials as an inhibitor of DNA gyrase (Scheme 54) [112].…”