82214-83-3Relevant academic research and scientific papers
Synthesis and radical scavenging activity of substituted Benzo [H] chromanols
Okayama, Yuta,Harada, Masanori,Morita, Mine,Mochizuki, Masataka,Inami, Keiko
, p. 865 - 878 (2017/06/13)
Benzo[h]chromanols, which possess a tocopherol moiety, have been reported to exhibit potent antioxidant activity. Several benzo[h]chromanols with various substituents (nitro, chloro, bromo, methyl, or amino groups at the position ortho to the phenolic OH group) were synthesized, and the second-order rate constants (k) of their reaction with the galvinoxyl radical were determined. The introduction of electron-withdrawing bromo, chloro and nitro groups decreased the activity, and the activity correlated well with the substituent effect. ortho-Aminobenzo[h]chromanol showed the highest radical scavenging activity among the compounds synthesized.
On the search for potential anti-Trypanosoma cruzi drugs: Synthesis and biological evaluation of 2-hydroxy-3-methylamino and 1,2,3-triazolic naphthoquinoidal compounds obtained by click chemistry reactions
Da Silva Jr., Eufranio N.,De Melo, Isadora M.M.,Diogo, Emilay B.T.,Costa, Verenice A.,De Souza Filho, José D.,Valen?a, Wagner O.,Camara, Celso A.,De Oliveira, Ronaldo N.,De Araujo, Alexandre S.,Emery, Flávio S.,Dos Santos, Marcelo R.,De Simone, Carlos A.,Menna-Barreto, Rubem F.S.,De Castro, Solange L.
experimental part, p. 304 - 312 (2012/07/27)
Five 2-hydroxy-3-substituted-aminomethyl naphthoquinones, nine 1,2,3-triazolic para-naphthoquinones, five nor-β-lapachone-based 1,2,3-triazoles, and several other naphthoquinonoid compounds were synthesized and evaluated against the infective bloodstream
Allylation of Carbonyl Compounds with Catalytic Amount of Indium
Araki, Shuki,Jin, Shun-Ji,Idou, Yoshiyuki,Butsugan, Yasuo
, p. 1736 - 1738 (2007/10/02)
Allylation of aldehyde and ketone, and prenylation of 2-chlorobenzoquinone were achieved by using a combination of a catalytic amount of indium(III) chloride and metallic aluminium or zinc.
Allylation of quinones bu allylic indium reagents
Araki, Shuki,Katsumura, Nobuhito,Butsugan, Yasuo
, p. 7 - 24 (2007/10/02)
Allylation of a variety of quinones by allylic indium sesquihalides was studied.Reactions of unsubstituted p-benzoquinone with allylindium, prenylindium, and geranylindium reagents gave, after oxidation with silver oxide, the corresponding allylated quinones in good yields.These reactions appear to proceed via 1,2-addition of the allylic indium reagents at the γ-carbon followed by sigmatropic rearrangement.Substituted quinones reacted with allylindium reagent giving excellent yields of allylquinols, whereas with prenylindium and geranylindium reagents, trisubstituted quinones gave diprenylcyclohexene-1,4-diones and 2,3-disubstituted quinones gave mixtures of prnylhydroquinones and diprenylcyclohexene-1,4-diones.In the prenylation of haloquinones, 1,2-addition, sigmatropic rearrangement, and elimination of indium(III) halide occurred in sequence yielding prenylquinones. 2-Hydroxy- and 2-methoxy-1,4-naphthoquinones gave α-addition products with prenylindium and cinnamylindium reagents.
Allylation of Quinones via Photoinduced Electron-Transfer Reactions from Allylstannanes
Maruyama, Kazuhiro,Imahori, Hiroshi
, p. 816 - 825 (2007/10/02)
Photochemical reactions of quinones with allylstannanes provided four types of products: adducts of allyl group to the carbonyl oxygens of quinones, adducts of allyl group to the olefinic carbons, adducts of allyl group to the carbonyl carbons, and hydroquinones.An electron-transfer mechanism was confirmed by 1H-CIDNP (Chemically Induced Dynamic Nuclear Polarization) method.This study suggests that a) photoinduced electron transfer from allylstannanes to quinones produces the corresponding quinone anion radicals and tin cation radicals, b) the tin cation radicals cleave to give allyl radicals as well as tin cation, and c) the allyl radicals attack the quinone anion radicals resulting in the formation of final products, allylated quinones.
Synthesis of Naturally Occuring Naphthoquinones: Deoxylapachol, 2,3-Di-(3-methyl-but-2-enyl)-1,4-naphthoquinone, 2-Methyl-3-(3-methyl-but-2-enyl)-1,4-naphthoquinone and Lapachol
Kapoor, N. K.,Gupta, R. B.,Khanna, R. N.
, p. 189 - 191 (2007/10/02)
Deoxylapachol (I), 2,3-di-(3-methyl-but-2-enyl)-1,4-naphthoquinone (II), 2-methyl-3-(3-methyl-but-2-enyl)-1,4-naphthoquinone (III) and lapachol (IV) have been synthesised by the prenylation of 1,4-naphthoquinone (V) (for I and II), 2-methyl-1,4-naphthoquinone (VII) (for III) and 2-hydroxy-1,4-naphthoquinone (IX) (for IV) by prenyl bromide.
