Synthesis and Characterization of New Cyclic Aminobenzoquinones

Abstract

The aim of this research is to synthesize and characterize new members of cyclic aminobenzoquinones. Mono amino substituted products, namely 2-chloro-5,6-dimethyl-3-(pyrrolidin-1-yl)-1,4-benzoquinone (2), 2-chloro-5,6-dimethyl-3-(piperidin-1-yl)-1,4benzoquinone (3), 2-chloro-5,6-dimethyl-3-morpholino-1,4-benzoquinone (4), and 2-chloro-5,6dimethyl-3-thiomorpholino-1,4-benzoquinone (5) have been synthesized by the nucleophilic substitution reactions between 2,3-dichloro-5,6-dimethyl-1,4-benzoquinone (1) and cyclic secondary amines with a green methodology using water as solvent. Structure determination of the new products (2-5) was established on the basis of FTIR, 1 H NMR, 13 C NMR, and mass spectrometry.

Discovery of a new family of heterocyclic amine linked plastoquinone analogs for antimicrobial evaluation

“…Futile efforts by changing the reaction conditions did not yield the desired product possibly due to steric hindrance of the bulky ortho substituent as the spatial arrangement of atoms or functional groups near the reacting site hindered the reaction from proceeding. PQ1 , PQ2 , PQ9 , and PQ10 were prepared before by our group (Tuyun & Yıldız, ), while the other PQ analogs are novel molecules.…”

“…The precursor ( 2 ) was synthesized using the reported method in the literature (Ryu & Lee, ). PQ1 , PQ2 , PQ9 , and PQ10 have been prepared according to the literature (Tuyun & Yıldız, ).…”

“…The title analog ( PQ10 ) was prepared according to the literature and identified by comparing its spectral properties to those reported for the analog in the literature (Tuyun & Yıldız, ).…”

Synthesis, Characterization, and Biological Evaluation of a New Hydrogen-Bonded Charge-Transfer Complex of 2-Amino-4-methoxy-6-methylpyrimidine

“…Furthermore, the complex presented an inhibition zone for certain bacterial strains equivalent to that for 30 mg of tetracycline. e high antimicrobial activity of the [(AMMP) 2 (DHBQ)] complex can be attributed to the presence of both pyrimidine and p-benzoquinone rings, which are known for their biological activities [55,56]. Furthermore, it has been reported in the literature that heterocyclic compounds with electron-donating methoxy group substituents at the para position of the aromatic rings exhibit excellent antimicrobial activity [57][58][59].…”

Highly conjugated isoindigo and quinoxaline dyes as sunlight photosensitizers for onium salt‐photoinitiated cationic polymerization of epoxy resins

“…When visible light is absorbed, these molecular complexes can enter an excited electronic state followed by charge transfer from the HOMO level of the donor molecule to the LUMO level of the acceptor 32 . More recently, the use of upconverting nanoparticles, 33 graphene oxide 34 and fullerene 35 and chemiluminescence 36 have been introduced as alternative wavelength‐shifting approaches for the initiation of cationic polymerization.…”