Wyniki wyszukiwania - BazTech

1

Transformations of chlorodibromomethyl-4-chlorophenyl sulfone into new compounds with potential pesticidal activity

Ochal Z., Wójcicki J.

Polish Journal of Applied Chemistry

|

2007

|

Vol. 51, nr 1-2

29-41

EN

The synthesis of chlorodibromomethyl-4-cfilorophcnyl sulfone derivatives as new potential pesticides is reported. The title sulfonc was obtained starting from chlorobenzene, its chlorosulfonation, reduction to the sulfinyl salt, which was transformed with bromofbrm or diehloroacetic acid natrium salt to dibromo-mcthyl-4-ch!orophenylsulfonc 4, or chloromcthyl-4-clilorophcnylsulfone 5. Sulfone 4 was chlorinated by hypohalite and sulfone 5 was brominated by bromine chloride or hypobromite to a final product 6. Chlorodibromomethyl-4-chiorophenyl sulfone was nitrated and then subjected to the SNAr reaction with amines and hydrazine to give 2-nitroaniline and 2-nitrophenylhydra7ioe derivatives. The last one was rransfonncd into hydrazonc, semicarbazide and tiosemicarbazidc derivatives.

2

Synthesis of (R) and (S)-2-[4-(4'-difluoromethylsulfonyl-2'-nitrophenylamino)phenoxy]propionic acid derivatives as new pesticides

Ochal Z., Gałązka J.

Polish Journal of Applied Chemistry

|

2006

|

Vol. 50, nr 1-2

13-27

EN

The synthesis of (R) and (S)-2-phenoxypropionie acid derivatives bearing difluoromethylsulfonyl-nitrophenyl group, such as: phcnoxypropionamides, phenoxypropionhydrazides, phenoxypro-pionhydrazones and phcnoxypropionsemicarbazides as a new compounds with potential pesticidal activity is reported. The title compounds were obtained starting from the proper phenol synthesized from difluoroniethyl-3-nitro-4-chlorophenyl sulfone and 4-aminophenole. Obtained phenol was transformed into optically active phenoxypropionic acid ethyl esters in reaction with (S)-(-)-tosy!oxy ethyl lactate and (R)-(+)-2-chloropropionic acid ethyl ester. They were hydrolyzed, and then obtained acids were converted into chlorides. Phenoxy acid chlorides were subjected to the reaction with amines. Phenoxypropionic acid ethyl esters are transformed in reaction with hydrazine hydrate into hydrazides, which were used to the reaction with aldehydes and isocyanates. Optical purity of the synthesized compounds were determined using HPLC equipped with chiral columns. Characteristic IR spectroscopic data and microelernentary analyses of the new products are reported.

3

Transformations of chlorodifluoromethyl-4-chlorophenyl sulfone into new compounds with pesticidal activity

Mizerski A., Ochal Z., Baran P.

Polish Journal of Applied Chemistry

|

2003

|

Vol. 47, nr 3

161-167

EN

The synthesis of chlorodifluoromethyl-4-chlorophenyl sulfone derivatives as new compounds with potential pesticidal activity is reported. The title sulfone was obtained in the three-step synthesis starting from 4-chlorothiophenol, then it was nitrated and subjected to the reaction SNAr. After reduction of the nitro group, compounds were reacted with carboxylic acids or their derivatives to give benzothiazole and benzoimidazole derivatives. Characteristic IR spectroscopic data and microelementary analyses of the novel products are reported.

PL

Opisano syntezę pochodnych sulfonu chlorodifluorometylowo-4-chlorofenylowego jako nowych związków o potencjalnej aktywności pestycydowej. Tytułowy sulfon otrzymano w trójetapowej syntezie wychodząc z 4-chlorotiofenolu, a następnie poddano go nitrowaniu i reakcjom SNAr. Po redukcji grupy nitrowej prowadzono reakcje z kwasami karboksylowymi lub pochodnymi kwasów i otrzymano szereg pochodnych benzotiazolu i benzoimidazolu. Przedstawiono charakterystyczne dane spektroskopowe IR oraz wyniki analizy elementarnej nowych związków.

4

Synthetic studies on some new diaryl sulphides and diaryl sulphones with fused heterocyclic rings

Kandeel M. M.

Bulletin of the Polish Academy of Sciences. Chemistry

|

2002

|

Vol. 50, No. 3

309-322

EN

The reaction of 2-amino-6-[(p-nitrophenyl)thio]benzothiazole (1) with a variety of reagents namely chloroacetyl chloride, chloropropionyl chloride, p-toluenesulphonyl chloride, phenyl isothiocyanate, phenacyl bromides has been carried out and their products were identified. Some of these products underwent ring closure reaction to afford fused tricyclic compounds. Compound 1 undergoes ring opening upon boiling with NaOH solution to give 2-amino-3-mercapto-4'-nitro diphenyl sulphide (2). Reaction of (2) with aromatic aldehydes, phenyl isothiocyanate, formic acid, carbon disulphide afforded the corresponding benzothiazole derivatives, while its reaction with chloroacetyl chloride or chloropropionyl chloride gave benzothiazine and benzothiazepine. All products were oxidized into the corresponding sulphones upon treatment with H(2)O/AcOH mixture.