N-Alkyl Imides and Their Reduction by Means of Lithium Aluminum Hydride

Abstract

During the past several years we have prepared a relatively large number of cyclic bases which have been screened for hypotensive activity as hydrochlorides and quaternary salts. We have found with the majority of compounds prepared in the several series studied so far that the bases could be prepared conveniently and in good yields by the reduction of the corresponding imides with lithium aluminum hydride. As a result of this continued study we have prepared a large number of N-alkyl-and N-dialkyl-aminoalkyl imides as intermediates in the synthesis of the desired bases.A survey of the literature concerning the particular series of imides that we wish to report here revealed that one t o several members had been reported in each series but that in many cases the physical data were scanty. Also, the previously reported imides, prepared by a variety of methods, are scattered in many sources in the literature. We have prepared the present four series of N-alkyl imides, in amounts varying from 4 to 90 grams, by a single general method and have assembled complete data on boiling points, melting points, densities, and refractive indices.In the present article we wish to report the N-alkyl succinimides from butyl through dodecyl (I) ; the N-alkyl-cis-A4-tetrahydrophthalimides, methyl through dodecyl (11) ; the N-alkyl-cis-3, 6-endomethylene-A4-tetrahydrophthalimides, butyl through dodecyl (111) ; and the N-alkyl hexahydrophthalimides, methyl through dodecyl (IV). 0 0 0 0

Tuning the size of supramolecular single‐chain polymer nanoparticles

“…2‐dodecyl‐(3ac,7ac)‐3a,4,7,7a‐tetrahydro‐4r,7c‐methano‐isoindole‐1,3‐dione was synthesized in a modified method to previously reported 29. Cis‐5‐norbornene‐2,3‐dicarboxylic anhydride (2.61 g, 15.9 mmol), 1‐dodecylamine (3.10 g, 16.7 mmol), and toluene (50 mL) was stirred while triethylamine (0.15 mL) was added.…”

Inhibition of glucocorticoid receptor transformation, subunit dissociation, and temperature-dependent inactivation by various N-substituted maleimides

“…Synthesis of TV-benzylsuccinimide was performed according to the method of Rice et al (1954). Analytical controls included thin-layer chromatography on plates precoated with silica gel F254 (0.25 mm) (Merck, Darmstadt, FRG).…”

4,7-Dihydro-, 4,5,6,7-tetrahydro-, and octahydroisoindoles (and methanoisoindoles). (Review)

“…Phthalimides and phthalimidines are similar in structure to isoindoles, are easily obtainable, and are therefore often used in the synthesis of isoindoles [2,3,5] and their isologs [7][8][9][10][78][79][80][81][82][83][84][85][86].…”

“…Rice and coauthors [7,8,[78][79][80] obtained series of hexa-and octahydroisoindoles and their "bridged" derivatives 52 with various substituents at the nitrogen. On the basis of these compounds quaternary salts 53 with clearly defined biological activity were obtained, e.g., see [7].…”