20677-52-5Relevant academic research and scientific papers
Selective Late-Stage Sulfonyl Chloride Formation from Sulfonamides Enabled by Pyry-BF4
Gómez-Palomino, Alejandro,Cornella, Josep
supporting information, p. 18235 - 18239 (2019/11/13)
Reported here is a simple and practical functionalization of primary sulfonamides, by means of a pyrylium salt (Pyry-BF4), with nucleophiles. This simple reagent activates the poorly nucleophilic NH2 group in a sulfonamide, enabling the formation of one of the best electrophiles in organic synthesis: a sulfonyl chloride. Because of the variety of primary sulfonamides in pharmaceutical contexts, special attention has been focused on the direct conversion of densely functionalized primary sulfonamides by a late-stage formation of the corresponding sulfonyl chloride. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides, sulfonates, sulfides, sulfonyl fluorides, and sulfonic acids. The mild reaction conditions and the high selectivity of Pyry-BF4 towards NH2 groups permit the formation of sulfonyl chlorides in a late-stage fashion, tolerating a preponderance of sensitive functionalities.
Aryl sulfonic acid ammonium salt compound, preparation method and application thereof (by machine translation)
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Paragraph 0027; 0036; 0040; 0041, (2018/03/25)
The invention discloses a aryl sulfonic acid ammonium salt compound, preparation method and application thereof, the main process expressed as follows: formula (I) indicated by the aryl sulfonic acid compound crude product as raw material, in the solvent with the structural formula (II) shown in mixed organic amine, to form the structural formula (III) as shown by a aryl sulfonic acid ammonium salt; the resulting structural formula (III) aryl sulfonic acid ammonium salt shown by the alkali soluble acid or directly to obtain the acid of formula (I) shown in the purification of compounds such as aryl sulfonic acid. The invention is primarily embodied in the [...]: through the low quality aryl sulfonic acid compound refining, effectively reduces the content of harmful impurities, improve the quality of the aryl sulfonic acid compound, reducing the pressure of the downstream use, the process is stable. (by machine translation)
Sulfide Oxidation and Oxidative Hydrolysis of Thioesters by Peroxymonosulfate Ion
Bunton, Clifford A.,Foroudian, Houshang J.,Kumar, Anurag
, p. 33 - 40 (2007/10/02)
Peroxymonosulfate ion, HSO5-, as OXONE, in aqueous MeCN readily converts aryl thiobenzoates, XC6H4CO*SC6H4Z (X = p-OMe, p-Me, H, p-Cl, p-CN; Z = p-OMe, p-Me, H, m-OMe, p-Cl, m-Cl, p-NO2) into carboxylic and sulfonic acids.Reactions are second order and have small substituent effects, with ρ ca. -0.6 based on ?m and ?p substituent parameters, but rates increase markedly with increasing water content in aqueous MeCN and entropies of activation are negative.The initial step is very similar to the oxidation of methyl aryl sulfides by HSO5- which has similar solvent and substituent effects.Enthalpies of activation are much lower for oxidation of the sulfides than of the corresponding esters but entropies of activation are similar.
Benzodioxole derivatives, processes for the manufacture thereof and corresponding pharmaceutical compositions
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, (2008/06/13)
The invention relates to novel benzodioxole derivatives of the general formula I STR1 in which R1 represents an unsubstituted or substituted, aliphatic, aromatic or heteroaromatic radical, alk represents an alkylene, alkenylene or alkylidene radical having a maximum of 5 carbon atoms, n1 represents 0, 1 or 2 n2 represents 0 or 1, R2, R3 and R4 each represents, independently of the others, hydrogen, lower alkyl, lower alkoxy or halogen, and A represents the radical --O--R5, wherein R5 represents hydrogen or an unsubstituted or substituted, aliphatic or araliphatic hydrocarbon radical, or A represents the radical STR2 in which either R6 and R7 each represents, independently of the other, hydrogen or lower alkyl, or R6 and R7 are bonded to one another and, together with the adjacent nitrogen atom, represent optionally lower alkyl-substituted tetra- to hexa-methyleneimino, 4-morpholinyl or 1H-tetrazol-1-yl, such as, for example, 5-methyl-6-phenylsulphonyl-1,3-benzodioxole-2-carboxylic acid. The invention relates also to salts of compounds of the general formula I in which A represents OR5 wherein R5 represents hydrogen, with bases, and to acid addition salts of compounds of the general formula I in which the radical R1 has a basic character and to processes for the manufacture of the above compounds and the salts thereof and to pharmaceutical compositions containing them. These novel substances have diuretic and supplementary uricosuric action and may be used, preferably in the form of appropriate pharmaceutical compositions, for the treatment of oedema and hypertension.
COMPARISON OF THE MECHANISMS OF SOLVOLYSIS OF ARENESULFONIC ESTERS OF BEZOIN IN METHANOL AND FORMIC ACID ON THE BASIS OF THE HAMMOND POSTULATE
Dement'eva, L. P.,Semenova, S. N.,Karavan, V. S.
, p. 654 - 657 (2007/10/02)
The kinetic of the methanolysis of the arenesulfonic esters of substituted benzoins p-XC6H4C(O)CH(OSO2C6H4Y)C6H5 (X = CH3O, H, Cl; Y = p-CH3O, p-CH3, H, p-Cl, m-Cl) at 30-50 deg C were studied, and it was established that unlike the previously investigated formolysis of these substrates (ρ+X o and ρY is opposite in character, which agrees with the Hammond postulate.The given contradiction is explained by the fact that the experimental temperature range is higher than the isoselectivity temperature.
