Microwave-Assisted Synthesis and Characterization of Certain Oximes, Hydrazones, and Olefins Derived fromβ-Keto Sulfones

Abstract

A new series ofβ-keto sulfone derivatives containing oximes4a–e, hydrazones5a, b, and chalcones7a–dwere prepared using microwave irradiation (MWI) by the reaction ofβ-keto sulfones3with hydroxyl amine, hydrazines, and aromatic aldehydes, respectively. The comparative study between microwave irradiation and conventional syntheses showed that MWI is effective in the synthesis of the title compounds through shortening of the reaction time and improvements in their yields. The structures of the synthesized compounds were established under the basis of their spectral data and X-ray single crystal analysis of compound5a. The crystal of5abelongs to triclinic space groupP-1, witha=5.7735 (2) Å,b=9.3224 (3) Å,c=13.1696 (5) Å,α=76.411 (1)°,β=89.571 (1)°,γ=79.9380 (9)°,Z=2, V=677.97 (4) Å3,Dc=1.513 Mg m−3,μ=0.44 mm−1,F(000)=320,R=0.026, andwR=0.070for 2690 observed reflections withI>2σ(I).

Synthesis and X-Ray Structure of (1Z,2Z)-1,2-Bis(2-(phenylsulfonyl)-1-(4-tolyl)ethylidene)hydrazine

“…However, the reaction of compound 3 with hydrazine hydrate in MeOH, EtOH, BuOH, THF, or AcOH/EtOH, under the previous conditions, gave a poor yield of compound 5 whereas using of AcOH gave the highest yield of 5 (78%). Recently, we have reported the reaction of sulfone 3 (R=Cl) with hydrazine hydrate in ethanol, in the presence of catalytic amount of acetic acid, at 90 ∘ C/100 W/30 sec to give hydrazone 4 (R=Cl), in 86% yield, as final isolable product [16].…”

Design, Synthesis, and Molecular Docking of 1-(1-(4-Chlorophenyl)-2-(phenylsulfonyl)ethylidene)-2-phenylhydrazine as Potent Nonazole Anticandidal Agent

“…epithelial cell line MCF10A by measurement of annexin-V binding by flow cytometry was performed according to the reported method with minor modification [45]. 14a-d, 15a, b, and 16a, b [29] and the newly synthesized compound 13 were evaluated in vitro for their antifungal activity, by inhibition zone technique, using four Candida species (C. albicans, C. krusei, C. parapsilosis, and C. glabrata). The mean values of the inhibition zone diameter obtained for compound 13 suggest that compound 13 possesses significant antifungal activity against C. albicans, C. krusei, and C. parapsilosis (Table 1).…”

“…In view of the facts mentioned above and as part of our ongoing effort to prepare biologically active agents [29][30][31][32][33][34][35][36], herein we present the design, synthesis, and preliminary biological evaluation of 1-(1-(4-chlorophenyl)-2-(phenylsulfonyl)ethylidene)-2-phenylhydrazine (13) as potent antifungal agent based on a novel nonazole scaffold. The mode of action of compound 13 to the potential receptor cytochrome P450 14 -sterol demethylase was investigated by molecular docking.…”

“…The MS (ESI) analysis of 13 showed a peak at / = 384.7 [M] + . In a previous study published recently, we synthesized compounds 14a-d, 15a, b, and 16a, b (Scheme 2) investigated here[29].…”

Oxidative Cleavage ofβ-Keto Sulfones via Nitrous Acid

“…This method has been widely utilized and its reaction mechanism has been reported [6]. In this study and in continuation of our interest in chemistry of -keto sulfones [7][8][9], we shall deal with the reaction of nitrous acid with -keto sulfones 3 and therefore the probable modes of formation of the corresponding carboxylic acids 12.…”