The reaction of sulfamic acid derivatives with epoxides

Тартаковский, В. А.; Ermakov, A. S.; Sigai, N. V.

doi:10.1007/bf00704210

Cited by 3 publications

(3 citation statements)

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“…They showed that these sulfamic acids reacting with epoxides gave hydroxysulfamates in 50−95% yields following the reaction shown in Scheme 3. 122 More than 10 products could be made by variation of R and R 1 in the starting materials.…”

Section: Solubility Conductance and Miscellaneous Studiesmentioning

confidence: 99%

“…Some years ago a Russian group carried out important studies on reactions of sodium, potassium, and ammonium alkylsulfamate salts with epoxides. They showed that these sulfamic acids reacting with epoxides gave hydroxysulfamates in 50–95% yields following the reaction shown in Scheme . More than 10 products could be made by variation of R and R 1 in the starting materials.…”

Section: Sulfamic Acidmentioning

confidence: 99%

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Sulfamic Acid and Its N- and O-Substituted Derivatives

2013

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Section: Solubility Conductance and Miscellaneous Studiesmentioning

confidence: 99%

Section: Sulfamic Acidmentioning

confidence: 99%

Sulfamic Acid and Its N- and O-Substituted Derivatives

2013

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“…We previously studied in detail reactions of sulfamic acid salts with epoxy derivatives [5,6] and found that this transformation can be used to obtain a wide series of the corresponding N-(2-hydroxyalkyl)sulfamates (compounds IaIc and Ie) in high yields. Some compounds I can be subjected to further modification.…”

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confidence: 99%

New Synthetic Approaches to Functionally Substituted 4,5-Dihydro-1,2,3-oxadiazole 2-Oxides

et al. 2005

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A practical procedure has been proposed for the synthesis of functionally substituted 4,5-dihydro-1,2,3-oxadiazole 2-oxides on the basis of sulfamic acid derivatives.Functionally substituted 4,5-dihydro-1,2,3-oxadiazole 2-oxides were synthesized for the first time by alkaline hydrolysis of the corresponding N-nitrosulfamides [1,2] or functionalized N-nitro-2-cyanoethylalkylamines [3]. In both cases, the initial materials were difficultly accessible compounds. Taking into account recent data, such compounds attract interest as nitrogen oxide donors [4], as well as components of gas-generating compositions.The goal of the present work was to develop a practical procedure for the preparation of both previously known and new functionally substituted 4,5-dihydro-1,2,3-oxadiazole 2-oxides. We previously studied in detail reactions of sulfamic acid salts with epoxy derivatives [5,6] and found that this transformation can be used to obtain a wide series of the corresponding N-(2-hydroxyalkyl)sulfamates (compounds IaIc and Ie) in high yields. Some compounds I can be subjected to further modification. For example, by nucleophilic substitution of the chlorine atom in Ic we obtained compounds Id and If (Scheme 1). The latter were brought into further syntheses without additional purification, for it was difficult to separate them from inorganic salts.The next stage of our study was aimed at selecting optimal conditions for nitration of compounds I. The nitration was performed using a mixture of nitric and sulfuric acids. Only in the reaction with N-(3-azido-2-hydroxypropyl)sulfamate Id we used a mixture of nitric acid and acetic anhydride to avoid replacement of the azido group by nitrate moiety. The yields of the corresponding N-nitro amines II varied from 70 to 90%. Nitroamines II were then converted into ammonium salts III by saturation of their solutions in diethyl ether with gaseous ammonia. It should be emphasized that this stage was simultaneously the final stage of purification of compounds II from nitrolysis products. Salts III were subjected to cyclization in methanol in the presence of an equimolar amount of alkali or in the absence of it. As a result, we isolated a series of 4,5-dihydro-1,2,3-oxadiazole 2-oxides IV having functional substituents in the 5-position; the overall yield was about 50% (Scheme 2). +1 &+ &+&+ &O 62 0 2+ ,F 1D1 &+ 1+62 0 2+ +1 &+ &+&+ 1 62 0 2+ ,G +1 &+ &+&+ 1&+ 62 0 2+ 62 0 ,I '0) +1 &+ &+5 62 0 2+ ,D B ,I 12 +1 &+ &+5 12 212 ,,D B ,,I 1+ 1 1 2 5 2+ 0H2+ 2 ,9D B ,9I 1+ 1 1&+ &+5 2 2 212,,,D B ,,,I M = Na, K; R = R' = H (a), CH 2 OCH 3 (b), CH 2 Cl (c), CH 2 N 3 (d); R = CH 2 OH, R' = CH 2 ONO 2 (e); R = CH 2 N(SO 3 M)CH 3 , R' = CH 2 N(NO 2 )CH 3 (f). M = Na, K. Scheme 1. Scheme 2.

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