1216-96-2Relevant articles and documents
A novel synthesized tyrosinase inhibitor: (E)-2-((2,4-dihydroxyphenyl) diazenyl)phenyl 4-methylbenzenesulfonate as an azo-resveratrol analog
Bae, Sung Jin,Ha, Young Mi,Kim, Jin-Ah,Park, Ji Young,Ha, Tae Kwun,Park, Daeui,Chun, Pusoon,Park, Nam Hee,Moon, Hyung Ryong,Chung, Hae Young
, p. 65 - 72 (2013/03/28)
We synthesized a novel series of (E)-2-((substituted phenyl)diazenyl)phenyl 4-methylbenzenesulfonate derivatives (2 and 3) and (E)-2-((substituted phenyl)diazenyl) phenol derivatives (4 and 5), and conducted an evaluation in order to determine their inhib
Rearrangement of differentially protected N-arylhydroxylamines
Porzelle, Achim,Woodrow, Michael D.,Tomkinson, Nicholas C. O.
experimental part, p. 5135 - 5143 (2009/06/17)
The rearrangement of a series of N,O-difunctionalised N-arylhydroxylamines to generate protected 2-aminophenols has been investigated. N-Boc-N-Aryl-O- acylhydroxylamines are stable, isolable compounds which rearrange smoothly at temperatures between 110 and 140°C. The corresponding N-Boc-N-aryl-O- sulfonylhydroxylamines were not isolated and rearrange to 1,2-difunctionalised aminophenols at room temperature in excellent yield. Deprotection of either the N- or O-substituents under standard conditions allows for further synthetic manipulation of either the aniline or phenol functionality. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Iodine-mediated cyclisation of thiobenzamides to produce benzothiazoles and benzoxazoles
Downer-Riley, Nadale K.,Jackson, Yvette A.
, p. 10276 - 10281 (2008/02/13)
Synthesis of benzothiazoles by reaction of iodine with thiobenzamides, which do not possess an ortho alkoxy or ester group, is described. The unlikely synthesis of benzoxazoles from reaction of 2-alkoxythiobenzamides with iodine is also reported.
Palladium-catalyzed heteroannulation leading to heterocyclic structures with two heteroatoms: A highly regio- and stereoselective synthesis of (Z)-4-alkyl-2-alkyl(aryl)idene-3,4-dihydro-2H-1,4,-benzoxazines and (Z)-3-alkyl(aryl)idene-4-tosyl-3,4-dihydro-2H-1,4-benzoxazines
Kundu,Chaudhuri,Upadhyay
, p. 20 - 29 (2007/10/03)
A highly convenient method has been developed for the synthesis of (Z)-4-alkyl-2-alkyl(aryl)idene-3,4-dihydro-2H-1,4-benzoxazines 9 and (Z)-3-alkyl(aryl)idene-4-tosyl-3,4-dihydro-2H-1,4-benzoxazines 34-38 through palladium - copper-catalyzed reactions. Aryl halides 7 reacted with 2-[Nalkyl(benzyl)-N-prop-2′-ynyl]aminophenyl tosylate 6 in the presence of (PPh3)2PdCl2 (3 mol %), CuI(5 mol %) in triethylamine at room temperature to yield 2-[N-alkyl(benzyl)-N-(3-aryl-prop-2′-ynyl)]aminophenyl tosylates 8 in extremely good yields (72-96%). The latter could then be cyclized with KOH in ethanol - water to Z-9 in a highly regio- and stereoselective manner. Similarly, palladium copper-catalyzed reaction of 2-(prop-2′-ynyloxy)aniline (21) with aryl iodides 7 led to 22-26 which after tosylation and cyclization with cuprous iodide in CH3CN in the presence of K2CO3 and Bu4-NBr led to the (Z)-3-alkyl(aryl)idene-4-tosyl 3,4-dihydro-2H-1,4-benzoxazines 34-38 in good overall yields. The Z-stereochemistry of the products was established from 1H NMR spectra, 3JCH values (between vinylic proton and methylenic carbon of the heterocyclic ring), NOE experiments, and X-ray analysis· The method was also found to be suitable for the synthesis of bis(benzoxazinylated) derivatives 17, 39, and 2-alkyl-3,4-dihydro-2H-1,4-benzoxazines 18. Our method for the synthesis of 3,4-dihydro-2H-1,4-benzoxazines is highly efficacious, using easily available starting materials under very mild conditions. Also the synthesis of some novel 5-substituted uracil derivatives 40 and 41 containing the benzoxazinyl moiety and of potential biological interest is being reported.
Flow cell electrosynthesis of phenylhydroxylamines. In situ reaction with arenesulfonyl chlorides. A convenient route to arenesulfinic acids synthesis.
Moinet, C.,Raoult, E.
, p. 214 - 221 (2007/10/02)
First, electrosyntheses of phenylhydroxylamines in a flow cell fitted with porous cathode and two counter-electrodes are described.Good yields are attained when electrolyses are performed in buffered aqueous organic or aqueous media.Reaction between p-toluenesulfonyl chloride and N-(3-chloro-4-methylphenyl)hydroxylamine, at the outlet of the cell, leads to a N-sulfonylated phenylhydroxylamine (N-addition); hydrolysis of this latter occurs in aqueous basic media to give the corresponding nitrosobenzene and sodium p-toluenesulfinate.As a result, some arenesulfinic acids have been directly obtained after reaction of arenesulfonyl chloride with sodium salt of 3-hydroxylaminobenzoate and 3-hydroxylaminobenzenesulfonate in aqueous phosphate buffer (pH 7).Next, an examination of the reaction of p-toluenesulfonyl chloride with phenylhydroxylamine in organic solvent, in the presence of triethylamine or of sodium carbonate, shows the importance of experimental conditions to control N-addition or O-addition.Addition of some arenesulfonyl chlorides to phenylhydroxylamine, in ether or dichloromethane containing sodium carbonate, gives only the N-sulfonylated phenylhydroxylamines.These compounds lead to nitrosobenzene and arenesulfinate anions in aqueous basic media.Aliphatic or aromatic sulfinic acids can be prepared in this way.
Substitution at Tetracoordinate Sulfur(VI). Rearrangement of 2-Aminoaryl Arenesulfonates to N-(2-Hydroxyaryl)arenesulfonamides
Andersen, Kenneth K.,Gowda, Gopala,Jewell, Linda,McGraw, Phillip,Phillips, Brian T.
, p. 1884 - 1889 (2007/10/02)
A series of eight 2-aminoaryl arenesulfonates upon treatment by strong bases rearranged intramolecularly to their corresponding N-(2-hydroxyaryl)arenesulfonamides as did the related tosylates derived from 2-amino-3-hydroxypyridine, 1-amino-2-naphthol, and
