Cyclic Sulfamates through [5+1] Cyclization of Sulfuryl Fluoride and Salicylic Amides: Synthesis and Chemical Transformations

Тип публікації :
Препринт
Дата випуску :
20 лютого 2026 р.
Автор(и) :
Viktoria S Sidorska
Serhii Aleksandrenko
Illia O. Doroshenko
Bohdan V. Vashchenko
Serhii Zhersh
Oleksandr O. Grygorenko
eKNUTSHIR URL :
DOI :
Журнал :
ChemRxiv
Цитування :
[APA 7] Viktoria, S. S., Serhii, A., Illia, O. D., Bohdan, V. V., Serhii, Z., & Oleksandr, O. G. (2026). Cyclic Sulfamates through [5+1] Cyclization of Sulfuryl Fluoride and Salicylic Amides: Synthesis and Chemical Transformations. ChemRxiv,. https://doi.org/10.26434/chemrxiv.15000251/v1
[ДСТУ] Cyclic Sulfamates through [5+1] Cyclization of Sulfuryl Fluoride and Salicylic Amides: Synthesis and Chemical Transformations / S. S. Viktoria та ін. ChemRxiv. 2026. DOI: 10.26434/chemrxiv.15000251/v1 (дата звернення: 11.09.2026).
An efficient sulfuryl fluoride-enabled synthesis of benzo[e][1,2,3]oxathiazine-4(3H)-one-2,2-dioxides from salicylic amides is described. Salicylamides were prepared on a multigram scale, and the corresponding cyclic sulfamates were synthesized via operationally simple one-pot Et3N-promoted [5+1] cyclization. In some cases, intermediate products of O-sulfonylation (fluorosulfates) were isolated. The method was suitable for both primary and secondary salicylic amides, albeit the use of a stronger base was necessary for sterically hindered substrates. The synthetic utility of the obtained heterocycles were demonstrated by their further chemical transformations. In particular, 4-chloro derivatives were obtained by deoxochlorination and converted into various cyclic aminosulfamates on a multigram scale. Derivatives bearing a bromine atom in the benzene ring were subjected to Pd-catalyzed couplings without affecting the sulfamate ring. Physicochemical properties of a representative virtual library derived from the synthesized scaffolds met the criteria of lead-likeness guidelines.
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