Synthesis of naphtho[2',3':4,5]imidazo[2,1-b][1,3]-thiazole-5,10-dione and naphtho[2',3':4,5]imidazo-[2,1-b][1,3]benzothiazole-7,12-dione

Khalafy, Jabbar; Ghezelbash, Zahra Dono; Mahmoody, Miri

doi:10.1007/s10593-010-0554-6

Cited by 3 publications

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“…The literature offers data that the reactions of 2,3‐dibromo‐1,4‐naphthoquinone with amines (methyl, propyl, butyl), arylamines, m, p‐aminophenols, 4‐aminopyridine, piperidine, ethylamine,, 2‐hydroxyethylamine, p‐toluidine, 2‐aminobenzothiazole, to produce 2‐Bromo‐3‐substituted‐l,4‐naphthoquinone derivatives.. It has been reported that the palladium‐catalyzed Suzuki‐Miyaura coupling reaction of 2,3‐Dibromonaphthoquinone with arylboronic acids affords the 2,3‐diarylnaphthoquinones .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Electrochemistry, DFT Calculations, Antimicrobial Properties and X‐ray Crystal Structures of Some NH‐ and/or S‐ Substituted‐1,4‐quinones

et al. 2018

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The NH-, NH-,S-substituted-1,4-naphthoquinones and NH-, Ssubstituted-1,4-benzoquinones have been synthesized from the reaction between quinones (2,3-Dibromo-1,4-naphthoquinone or p-benzoquinone) and different amines. The structures of the compounds have been confirmed using FTIR, UV-Vis, 1 H-NMR, 13 C-NMR, mass MS(ESI) spectrometry and cyclic voltammetry (CV). The ground state energies of the molecules have been estimated using B3LYP functional with different basis sets based on time dependent density functional theory (TD-DFT). The theoretical ΔE gap values obtained from TD-DFT calculations have been compared with UV visible spectroscopy results. Antibacterial and antifungal activities of the synthesized compounds have been evaluated against Escherichia coli, Staphylococcus aureus and Microsporum canis, Trichophyton mentagrophytes, respectively. Two representative crystal structures of quinone derivatives, 2-(4-Fluorophenylamino)-3-bromonaphthalene-1,4-dione and 2-(3,5-Dimethylphenylthio)cyclohexa-2,5-diene-1,4-dione, are reported with CCDC 1811265 and CCDC 1811263, respectively.

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