Interaction of 5-Substituted 1,4-Naphthoquinones and Amino Thiotriazoles: Reaction Ways and Regioselectivity

Abstract

Abstract.1 Reactions of nucleophilic substitution between 5-R-2,3-dichloro-1,4-naphthoquinones and 4-amino-5-heteryl-4H-1,2,4-triazoles-3-thiols were carried out. It is shown that the interaction can take place in two alternative ways and the reaction direction is controlled by reaction conditions. Search of differences in atoms reactivity in investigated molecules by comparing the calculated Fukui atonic indices was conducted. The influence of electron donor and electron acceptor substituent in 2,3-dichloro-1,4-naphthoquinone 5 th position on the nucleophilic substitution reaction regioselectivity was shown experimentally. Comparison of obtained 1 H NMR spectra with DFT calculated for both possible isomers of obtained products allowed to uniquely attribute synthesized compounds to relevant structures. The synthesized compounds were characterized by IR, 1 H NMR, 13C NMR spectroscopy and elemental analysis.

The (1H-Tetrazol-1-yl)arenediazonium Salts as Convenient Reagents for Quinones Arylation: Synthesis of 1,3-Benzoxathiol-2-ones and Naphtho[2,1-d][1,3]oxathiol-2-ones Bearing (1H-Tetrazol-1-yl)phenyl Motif

“…It should be noted that the high reactivity of tetrazolylarylquinones indicates their synthetic potential, which can be realized in a number of transformations. 61,62 Benzoxathiolones containing a phenolic group are known to react well with acylating and alkylating reagents. 59,60,63 5-Hydroxy-7-tetrazolylphenyl-1,3-benzoxathiol-2-ones 8a-f were readily acylated with acetic anhydride in the presence of hydrochloric acid by short heating of the reaction mixture.…”

Synthesis, Biological and Acidic Properties of Novel 2-Methoxy-6-[(3-Alkyl/Aryl-4,5-Dihydro-1H- 1,2,4-Triazol-5-one-4-yl)-Azomethin]-Phenyl p-Nitrobenzoate Derivatives

“…( 2 ) with 2-(p-nitrobenzoxy)-3methoxybenzaldehyde (3), which was synthesized by the reactions of 2-hydroxy-4-methoxybenzaldehyde with pnitrobenzoyl chloride by using triethylamine. On the other hand, the reactions of compounds 4 with acetic anhydride gave 2-methoxy-6-[(1-acetyl-3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)-azomethine]-phenyl pnitrobenzoates (5). The structures of the novel compounds were determined utilizing elemental analysis, IR, 1 H-NMR, 13 C-NMR, and UV spectroscopy.…”

“…In particular, 1,2,4triazole derivatives exhibit a wide range of biological actions, including anticancer, antitumor, antibacterial, antioxidant, anti-inflammatory, and antipsychotic activities. [1][2][3][4][5][6][7][8][9] Furthermore, among many organic scaffolds, Schiff bases with an azomethine linkage are well-documented as promising and modifiable molecules in drug discovery. Several articles, about the synthesis of some Schiff bases with 4,5-dihydro-1H-1,2,4-triazol-5-one ring have also been published.…”

Features of (Benzo)Imidazo[2,1-b][1,3]thiazine Mezylates Reaction with Nucleophilic Reagents

“…11 Nucleophilic substitution reaction in basic scaffolds is one of the powerful tools for structural modification of biologically attractive heterocyclic compounds. [15][16][17] This, in turn, prompted researchers both to search for new variants of such reactions based on available substrates and to involve new nucleophilic reagents. Generally, the use of nucleophilic substitution reactions in heterocyclic cores yielded a number of compounds interesting in terms of structure and properties, which can directly be used as objects of bioscreening studies, and act as synthetic blocks for the construction of more complex molecular structures.…”