The Synthesis of Arylsulfonylphthalimides and Their Reactions with Several Amines in Acetonitrile

Abstract

In this study, several N-(p-substituted-arylsulfonyl)phthalimides (1a-e) were synthesized. The synthesized compounds were then examined with respect to their substitution reactions with t-butylamine, diethylamine, cyclohexylamine, and trans-1,2-diaminocyclohexane in acetonitrile. In order to determine the mechanism, substituent effect, activation entropy, and nucleophile effect were used as criteria

Metal‐ and Catalyst‐Free Synthesis of 2‐Substituted‐Phthalimides Using 2‐(Arenesulfonyl)Phthalimide as Key Reagents

“…[20][21][22][23] Kurtuk and Ozturk studied the reaction of arenesulfonyl phthalimides with amines and proposed the formation of a product, though its characterization was not reported. [24] In the current study, we report that arensulfonylphthalimides are excellent reagents for easy access to 2-substituted phthalimides. We explored the scope of reactions of arensulfonyl succinimides and arenesulfonyl phthalimides with various amines and amino acids and found great similarity in chemical behavior with the corresponding cyclic anhydrides (Figure 3).…”

“…Melting points are General procedure for the preparation of N-substituted arenesulonyl phthalimides (3) and arenesulfonyl succinimide (5): Prepared by modification of reported methodology. [18,21,24,25,29] In a dry flask, a mixture of arenensulfonyl chloride (1 equiv., 30.98 mmol,)…”

“…Product 6 a was fully characterized by 1 H NMR, 13 C NMR, and HRMS and found to be different from what was previously proposed by Kurtuk and Ozturk. [24] They studied the reaction of arenesulfonyl phthalimides with amines and proposed the To study differences in reactivity between the alicyclic and aliphatic amines, compound 3 was subjected to a series of reactions with different amines of both classes. Six different aniline derivatives (Table 2) were tested under these optimized conditions, and all phthalimide products were recovered in high yields.…”

“…Although the synthesis of arenesulfonyl phthalimide derivatives from phthalimide and the corresponding arenesulfonyl chloride is easy, [18,19] only a few studies are found to explore the chemical scope of arenesulfonyl phthalimide compounds [20–23] . Kurtuk and Ozturk studied the reaction of arenesulfonyl phthalimides with amines and proposed the formation of a product, though its characterization was not reported [24] …”

Tosyl ester(s) of and945-hydroxy acid(s) Synthesis and antimicrobial studies

“…Organo Sulfur compounds find a wide range of chemical, medicinal, biomedical and industrial applications due to their low cost and useful properties such as solubility in aqueous and organic solvents, metal complexing ability, biological compatibility and ease of chemical modification [3][4][5]. The various methods of preparation of tosyl esters from aliphatic alcohols, aromatic acids, sulfonic acids and phenols have been reported [6][7][8][9][10][11].…”