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Synthesis, Alkylation and Reduction of 4‐Aryl‐2 H ‐1,2,3‐benzothiadiazine 1,1‐dioxides
Author(s) -
PorcsMakkay Márta,
Gyűjtő Imre,
Lukács Gyula,
Komáromi Anna,
Tóth Gábor,
Garádi Zsófia,
Simig Gyula,
Volk Balázs
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201901212
Subject(s) - benzothiadiazine , chemistry , alkylation , benzophenone , hydrazine (antidepressant) , aryl , medicinal chemistry , reactivity (psychology) , alkyl , combinatorial chemistry , organic chemistry , catalysis , medicine , alternative medicine , chromatography , pathology
ortho ‐(2‐Aryl‐1,3‐dioxolan‐2‐yl)benzenesulfonyl chlorides obtained from benzophenone ketals by directed ortho ‐lithiation chemistry were cyclized either with hydrazine monohydrate or with acetohydrazide to furnish variously substituted 4‐aryl‐2 H ‐1,2,3‐benzothiadiazine 1,1‐dioxides. Alkylation of benzothiadiazine dioxides with alkyl iodides under basic conditions was elaborated, revealing significant differences compared to the reactivity of 4‐unsubstituted ones. Hydrogenation of the C=N double bond in the presence of platinum(IV) oxide is also described. Detailed NMR studies and DFT calculations supported the structure elucidation of the compounds.