The Synthesis and Reactions of Some Cyclic Imides¹

Potential antitumor agents. 23. 4'-(9-Acridinylamino)alkanesulfonanilide congeners bearing hydrophilic functionality

“…In an extension of promising inhibitory results in vitro against Histoplasma capsulatum, correlated earlier using substituent constants developed by regression analysis with 77 disulfides, one symmetrical and 14 unsymmetrical disulfides were prepared (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17). About half were active in vitro against H. capsulatum (and one against Candida albicans).…”

“…The trithiopercarbamate moiety (1) has been one of the most promising,2,3d,f'g particularly with the nitrogen atom Finally, five other disulfides of varied structure, predicted to be inhibitory from their substituent constants, were prepared and tested (13-17 in Table I). Table I lists all compounds tested (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17), together with values calculated where possible for the minimum inhibitory concentrations (MIC).3g…”

“…Since all the amines produced on reduction bear electron-donor substituents, they are readily autoxidized and the products resulting from the catalytic absorption of the theoretical amount of hydrogen have accordingly been coupled directly with a 9-chloroacridine with minimum further manipulation. Addition of thiolacetic acid to methyl acrylate provides methyl S-acetyl-3-mercaptopropionate8 and following oxidation (C12-H20) provided 2-methoxycarbonylethanesulfonyl chloride.9" 11 2-Methoxycarbonyl-4'nitroethanesulfonanilide, necessary for 34, is readily prepared from this sulfonyl chloride. Saponification of the methyl ester in the latter sulfonanilide provided the corresponding acid necessary for elaboration of 33.…”

An efficient synthesis of 3-ethoxypyrrolidine-2,5-diones and cis-2,3,3a,6a-tetrahydrofuro[2,3-c]pyrrole-4,6(5H)-diones from β-cyanocarboxylic acids

“…Usually, succinic acids are obtained by the hydrolysis of the cyano group of dinitriles, 10 whereas, procedure for the synthesis of succinimides, without carrying out first the hydrolysis of the CN group, is underexplored. 11 Recently it has been reported that succinimides can also be synthesized by addition reactions of amines to olefinic bond of maleimides, 12 by ring expansion of β-lactams, 13 by carbonylation reactions of alkynes 14 and α,β-unsaturated amides 15 or biotransformation of maleimides promoted by fungi. 16 However, these methods, except one which is carried out by the reaction of amines with maleimides, involve catalysts of difficult access and reaction mechanisms still poorly understood.…”

A New and Efficient Synthesis of 2-Aminobenzothiazoles Derivatives from O-nitroaniline

“…Hoffmann 10 first reported the formation of 2-anilinobenzothiazole from the reaction of 2-aminothiophenol and phenyl isothiocyanate. Some groups have synthesised aminobenzothiazoles by cyclisations of substituted anilines with the help of potassium and ammonium thiocyanates [11][12][13][14][15] in the presence of bromine as catalyst. Phenylthiourea derivatives have also been employed for the synthesis of these important compounds.…”