ChemInform Abstract: Synthesis and a Study of the Properties of the Dioximes of the Adamantane Series.

Abstract

The 3‐substituted adamantane‐1‐carboxylic acids (I) are converted to the bromomethyl ketones (II) following literature procedures.

(4-(Adamantan-1-yl)-1-(isopropyl)-1H-imidazol-2-yl)methanol

“…The synthesis of 5 requires five steps from commercially available 1-acetyladamantane and is shown in Scheme 1; the NMR spectra of the product and intermediates are provided in the Supplementary Material. The α-brominated ketone precursor 2 has been reported but was previously synthesized by different routes [9][10][11]; our approach is adapted from a procedure used for the synthesis of 1-bromo-3-methyl-2-butanone and has been successfully carried out on up to a 10 g scale [12]. The next two steps (amination with isopropylamine and cyclization with formamide to give 3) are adapted from a reported synthesis of other closely related 1,4-disubstituted imidazoles [13].…”

A mild and efficient synthesis of aminofurazans

“…24 Later, from time to time, other researchers have used the reaction of α-bromoketones with hydroxylamine to accomplish glyoxime preparation with low to moderate yields, together with a range of byproducts. 25 As a result, only a limited number of glyoximes were synthesized by this method.…”

Synthesis and antiviral activity of several quinoline derivatives

“…The goal of the present work was to find new antiviral drugs in a series of compounds (I -XIV). 2-Mono-and 2,6-disubstituted quinoline-4-carboxylic acids I, IV, VI, and VIII were prepared by Pfitzinger cyclization of the corresponding methylketones with isatin in basic medium [3,4]. Methyl and ethyl esters II, V, VII, IX, and X were synthesized by esterification of the acids with alcohols in the presence of H 2 SO 4 [4].…”