2016
DOI: 10.1016/j.crci.2016.05.024
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α-Amination and the 5-exo-trig cyclization reaction of sulfur-containing Schiff bases with N-phenyltriazolinedione and their anti-lipid peroxidation activity

Abstract: Available online xxxx This work is dedicated to the memory of Professor Yiannis Elemes. Keywords: Triazolinedione Amino acid Schiff base 1,2-Dipole a-Amination 5-exo-trig cyclization a b s t r a c t Triazolinedione quenches efficiently the 1,2-dipoles from Schiff bases of glycine esters which are formed via a [1,2-H]-prototropic shift of their a-hydrogens, and affords the respective a-aminated products in good yields. Competition experiments show a stabilization of the 1,2-dipole from the sulfide substituent. … Show more

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Cited by 7 publications
(6 citation statements)
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“…However, recent advances in asymmetric synthesis have provided highly efficient and convenient protocols for achieving axially chiral molecules in an enantioselective fashion, which also provides new opportunities for in‐depth investigations into the bioactivities of a diverse range of functional molecules bearing enantio‐specific stereogenic axes 35–49 . Meanwhile, multifunctionalized urazole derivatives have demonstrated excellent biological activity against pathogens, including fungi, bacteria and viruses 50–58 . As a continuing research program in our laboratory, we are extremely interested in the potential of urazole derivatives bearing axial chiralities in the development of novel pesticides with high antiplant virus efficiency and low nontarget biological risk (Fig.…”
Section: Introductionmentioning
confidence: 99%
“…However, recent advances in asymmetric synthesis have provided highly efficient and convenient protocols for achieving axially chiral molecules in an enantioselective fashion, which also provides new opportunities for in‐depth investigations into the bioactivities of a diverse range of functional molecules bearing enantio‐specific stereogenic axes 35–49 . Meanwhile, multifunctionalized urazole derivatives have demonstrated excellent biological activity against pathogens, including fungi, bacteria and viruses 50–58 . As a continuing research program in our laboratory, we are extremely interested in the potential of urazole derivatives bearing axial chiralities in the development of novel pesticides with high antiplant virus efficiency and low nontarget biological risk (Fig.…”
Section: Introductionmentioning
confidence: 99%
“…Azo compounds have been used in various fields in science, medicine, and technology, It gave results of great significance in life, and azo compounds have the ability to have biological effectiveness [3,4).The compounds that have the benzamidazole group have been used in the treatment of ulcers and giadra inflammation in children [5,6).azo-schiff base were involved in many biological reactions in inhibiting DNA, RNA and protein synthesis [7-10]azo-schiff base compounds were used in the manufacture of dyes, due to the intensity of the coloration shown by these ligands, as a result of the non-positioning of the pi electrons and their containment of the azo and azo methene groups and their uses in dyeing fabrics and polyester, acrylic and nylon threads [11].In the field of analytical chemistry, the dominant color characteristic of this type of compounds and their complexes formed with metallic ions in their aqueous and organic solutions were exploited in spectroscopic analyzes, and they are called spectroscopic reagents [12]. In direct color estimation methods to estimate negative ions in solutions [13], azo compounds were used in the field of physical chemistry, in the study of adsorption on a surface of silicon dioxide [14] and in photography [15] and photo sensitizers [16][17][18][19] In photovoltaic applications [20] metallic complexes were used in the manufacture of solar cells [21].It has also been used in agriculture as insecticides and some agricultural pests, due to the presence of effective groups such as azo and azomethene [21] It has been shown in the field of medicine the possibility of using the azo-base compounds as anti-carcinogens, because they form complexes with ions of the transitional elements that have the ability to bind to the DNA bases by coordinating bonds with the nitrogen atoms in the DNA bases to form a chelate ring [22,23]While another type of azo-schiff base compounds was used as an antioxidant [24]and was also used to estimate the level of fluorine in toothpaste and mouthwash solution [12].Yingjie Zhang indicated in the case of treatment against cancerous tumors that the metal complexes exploit the difference between cancerous and normal cells in the direction of identifying harmful cells [25]. and they can also be used.…”
Section: Introductionmentioning
confidence: 99%
“…Here, we report the design and testing of the bis(alkylthio) imines, which are key compounds, used for the antioxidant (18) and anti-lipid peroxidation system (19).…”
Section: Introductionmentioning
confidence: 99%
“…Our total synthesis of (Figure 1) began with the preparation of glycine ethyl ester, the key amino acid fragments required for the synthesis of bis-sulfur substituted glycine ethyl ester via the known procedure (18,19).…”
Section: Introductionmentioning
confidence: 99%