A simple and efficient method has been developed for the synthesis of various 2-quinoxalinone-3-hydrazone derivatives using microwave irradiation technique. The series of 2-quinoxalinone-3-hydrazone derivatives synthesized, were structurally confirmed by analytical and spectral data and evaluated for their antimicrobial activities. The results showed that this skeletal framework exhibited marked potency as antimicrobial agents. The most active antibacterial agent was 3-{2-[1-(6-chloro-2-oxo-2H-chromen-3-yl)ethylidene]hydrazinyl}quinoxalin-2(1H)-one, 7 while 3-[2-(propan-2-ylidene)hydrazinyl]quinoxalin-2(1H)-one, 2 appeared to be the most active antifungal agent.
Can. J. Chem. 57,1384 (1979. Acetolyses of trianisyl[2-14C]viny1 bromide (1-Br-2-14C) were carried out in the presence of various amounts of added NaOAc or NaOAc and LiBr. Scramblings of the isotopic label from C-2 to C-1 arising from 1,2-anisyl shifts in the trianisylvinyl cation were observed in both the reaction product and the recovered, unconsumed reactant. The results indicate that the relative contribution of the 1,2-shift process is decreased with an increase in the amount of NaOAc or LiBr, in support of a mechanism involving formation of the dissociated trianisylvinyl cation which will competitively undergo 1,Zanisyl shift to give scrambling, be captured by Br-ion and return to scrambled starting material, and be captured by OAc-ion to give scrambled product. The results are also compared with previous data from solvolyses of triphenyl[2-14C]vinyl bromide and the differences are discussed.CHOI CHUCK LEE, URSULA WEBER et CRAIG A. OBAFEMI. Can. J. Chem. 57,1384Chem. 57, (1979. On a effectue l'ac6tolyse du bromure de trianisyl[2-14C]vinyle (1-Br-2-14C) en presence de quantites diverses de NaOAc ou de NaOAc et de LiBr. On a observe des echanges des isotopes marqueurs du C-2 vers C-1 provenant de transpositions-1,2 des anisyles dans le cation trianisylvinyle tant dans le produit de la reaction que dans le reactif r6cup6rk qui n'avait pas rkagit. Les rksultats indiquent que la contribution relative aux transpositions-1,2 diminue avec une augmentation de la quantite de NaOAc ou de LiBr; ceci est en accord avec un mecanisme impliquant la formation du cation trianisylvinyle dissocit qui subira des reactions cornpetitives soit de transpositions-1,2 donnant lieu a des echanges des isotopes soit des reactions oiI l'ion est piege par du Br-et donne lieu a une reaction de retour redonnant le produit de depart oiI il s'est produit des echanges ou des reactions ou Pion est piege par des ions OAc-qui fournissent des produits oiI il s'est effectue un khange. On compare aussi ces rksultats ceux obtenus anttrieurement lors de la solvolyse du bromure de triph&nyl[2-14C]vinyle et on discute des differences.[Traduit par le journal]The degenerate rearrangement arising from a 1,2-anisyl shift across the double bond in the trianisylvinyl (tris(p-methoxypheny1)vinyl)) cation was first reported from this laboratory in 1975 (1). For example, in the reaction of triani~~l[2-~~C]vinyl bromide (1-Br-2-13c) with HOAc-AgOAc, 13C nmr analysis of the product showed about 20% scrambling of the label from C-2 to C-1 (1). Similarly, using D-labeling and l H nmr analysis, Rappoport and co-workers (2) found that the NaOAc buffered acetolysis of 1,2-dianisyl-2-p-(2H3)methoxyphenylvinyl bromide (1-Br-methoxy-d,) gave 35 f 2% rearrangement1 arising from 1,2-anisyl shifts. It was also noted that when the NaOAc buffered acetolysis was carried out in the presence of an excess of Bu4NBr, 4 f 1.5% rearrangement was observed in the recovered reactant (2). Earlier, Rappoport and Gal (3) had reported that the unbuffered acetolysis of 1-Br gave irregular ...
Keywords: 3-hydrazinoquinoxalin-2(1H)-one, imines, Gram-positive bacteria.Over the years it has been established that quinoxalines are, in general, relatively easy to prepare [1-3], and many derivatives have been synthesized with the aim of obtaining biologically active materials [4,5]. Some quinoxaline and quinoxalinone derivatives have been reported to show antimicrobial [6,7], antiinflammatory [8], antifungal [9], anticancer [10], antiviral [11], antimalarial [12], anticonvulsant [13], antidepressant [14], antitubercular [15], antibacterial [16], and antithrombotic [17] activities. Thermal and chemically stable polyquinoxalines (PQs) find potential applications as films, coating adhesives [18], ultrafiltering materials, and composite matrices that demand stability in harsh environment [19]. In a similar manner the synthesis of novel pyrazole derivatives [20] and evaluation of their chemical behaviors have gained more importance in recent decades for biological [21-23], medicinal [24], and agricultural [25] purposes. Although numerous methods are available for construction of pyrazoles [26,27], only little attention has been given to the pyrazolysis of quinoxalinone derivatives [28]. For instance, 1,3-dipolar cycloadditions of azomethine imines, available by acid catalyzed treatment of 3-pyrazolidinone with acetone and butyraldehyde, respectively, were studied [29]. The photoluminescence and electroluminescence of some new 1H-pyrazolo-
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