Some sulfonyl derivatives of phenoxyacetamide

1978 ◽  
Vol 31 (12) ◽  
pp. 2669 ◽  
Author(s):  
RJ Cremlyn ◽  
RW Pannell
Keyword(s):  
Carbonyl Compounds ◽  
Sulfonyl Chloride ◽  
Chlorosulfonic Acid ◽  
Sulfonyl Chlorides ◽  
Phenoxyacetic Acids ◽  
Derivatives Of

Phenoxyacetamide (2) by treatment with chlorosulfonic acid gave the 4- sulfonyl chloride (3); this was characterized by preparation of the sulfonamide (4) and the sulfonohydrazide (5). The latter compound has been converted into five hydrazones (6) by condensation with the appropriate carbonyl compounds; with acetylacetone cyclization occurred to form the 3,5-dimethylpyrazole (7). 2,4-Dichloro- and 4-chloro-2- methyl-phenoxyacetamides were chlorosulfonated to the corresponding 6- sulfonyl chlorides (8) and (10), and these were characterized as the sulfonohydrazides (9) and (11). In contrast, attempts to chlorosulfonate 2,4-dichloro- and 4-chloro-2-methyl-phenoxyacetic acids were unsuccessful, and the reasons for this failure are briefly discussed.

scholarly journals Synthesis , characterization and biological activity study of N-substituted sulfonamido maleimides substituted with different heterocycles

2010 ◽  
Vol 7 (1) ◽  
pp. 641-653
Author(s):  
Baghdad Science Journal
Keyword(s):  
Sulfonyl Chloride ◽  
Chlorosulfonic Acid ◽  
Second Step ◽  
Klebsiella Pneumonia ◽  
Microbiological Activity ◽  
Sulfonyl Chlorides ◽  
The Third ◽  
Fourth Step ◽  
Cyclic Imides ◽  
Sulfonamide Group

Eighteen new cyclic imides (maleimides) conncted to benzothiazole moiety through sulfonamide group were synthesized via multistep synthesis.The first step involved preparation of two maleamic acids N-phenylmaleamic acid and N-benzylmaleamic acid via reaction of maleic anhydride with aniline or benzyl amine.Dehydration of the prepared amic acids by treatment with acetic anhydride and anhydrous sodium acetate in the second step afforded N-phenylmaleimide and N- benzyl maleimide which in turn were treated with chlorosulfonic acid in the third step to afford 4-(N-maleimidyl) phenyl sulfonyl chloride and 4-(N-maleimidyl) benzyl sulfonyl chloride respectively.In the Fourth step of this work each one of the two prepared maleimidyl sulfonyl chlorides was introduced in reaction with nine substituted-2-amino benzothiazole compounds producing nine N-(4-(N-substituted benzothiazole -2-yl) sulfonamido phenyl) maleimides and nine N-(4-(N-substituted benzothiazole-2-yl)snlfonamido benzyl) maleimides.More over another new six sulfonamide phenyl and benzyl maleimides substituted with other heterocycles (pyridine and phenazone )were prepared via reaction of 4-(N-maleimidyl) phenyl and benzyl sulfonyl chlorides with heterocyclic amines including (2-amino pyridine,4-amino-pyridine,4-aminophenazone). Microbiological activity of the prepared compounds against two typs of bacteria(staphylococcus aureus and klebsiella pneumonia) and (candida albicans) fungi were evaluated and the results showed that these compounds have good antibacterial and good antifungal activities.

Study of the structure and reactivity of nitrogen-containing derivatives of carbonyl compounds

1968 ◽  
Vol 17 (5) ◽  
pp. 940-944
Author(s):  
Yu. P. Kitaev ◽  
B. L. Moldaver ◽  
I. M. Skrebkova ◽  
V. G. Yakutovich
Keyword(s):  
Carbonyl Compounds ◽  
Derivatives Of

scholarly journals Nucleofugal behavior of a β-shielded α-cyanovinyl carbanion

2018 ◽  
Vol 14 ◽  
pp. 3018-3024
Author(s):  
Rudolf Knorr ◽  
Barbara Schmidt
Keyword(s):  
Michael Addition ◽  
Carbonyl Compounds ◽  
Room Temperature ◽  
Experimental Conditions ◽  
Metal Free ◽  
Metal Derivatives ◽  
Carbonyl Addition ◽  
Derivatives Of

Sterically well-shielded against unsolicited Michael addition and polymerization reactions, α-metalated α-(1,1,3,3-tetramethylindan-2-ylidene)acetonitriles added reversibly to three small aldehydes and two bulky ketones at room temperature. Experimental conditions were determined for transfer of the nucleofugal title carbanion unit between different carbonyl compounds. These readily occurring retro-additions via C–C(O) bond fission may also be used to generate different metal derivatives of the nucleofugal anions as equilibrium components. Fluoride-catalyzed, metal-free desilylation admitted carbonyl addition but blocked the retro-addition.

Oxidative reaction of 2-aminopyridine-3-sulfonyl chlorides with tertiary amines

2016 ◽  
Vol 22 (6) ◽  
Author(s):  
Huiping Wei ◽  
Gaigai Wang ◽  
Binbin Li ◽  
Jianjun Huang ◽  
Haiyan Li ◽  
...  
Keyword(s):  
Aerobic Oxidation ◽  
Sulfonyl Chloride ◽  
Dual Role ◽  
Tertiary Amines ◽  
Oxidative Reaction ◽  
Sulfonyl Chlorides

Abstract2-Aminopyridine-3-sulfonyl chlorides undergo a reaction with tertiary amines in the presence of air to produce sulfonylethenamines. The 2-aminopyridine-3-sulfonyl chloride apparently plays a dual role in the process promoting the aerobic oxidation of the amine and electrophilically trapping the resulting enamine.

Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones

Synthesis ◽  
2020 ◽  
Vol 52 (15) ◽  
pp. 2259-2266
Author(s):  
Mikhail Krasavin ◽  
Dmitry Dar’in ◽  
Grigory Kantin ◽  
Olga Bakulina
Keyword(s):  
Aqueous Medium ◽  
Organic Synthesis ◽  
Sulfonyl Chloride ◽  
One Pot ◽  
Sulfonyl Chlorides ◽  
Sulfonyl Azide ◽  
Diazo Reagents

A convenient one-pot approach to the preparation of α-diazo-β-ketosulfones from sulfonyl chlorides is described. It involves the conversion of the sulfonyl chloride to sodium sulfinate, alkylation of the latter with α-haloketones followed by diazo transfer using the ‘sulfonyl-azide-free’ (‘SAFE’) protocol in aqueous medium. The simple and expedient method relies on readily available starting materials and provides facile access to a wide variety of valuable diazo reagents for organic synthesis.

Sign in / Sign up

Export Citation Format

Share Document