SOME REACTIONS OF N-{3-[(ARYL-1-SULFONYL)IMINO]-6-OXOCYCLOHEXA-1,4-DIENЕ-1-YL}BENZAMIDES

Authors

  • Svetlana A. Konovalova Донбаська державна машинобудівна академія, Ukraine https://orcid.org/0000-0003-3410-2550
  • Anatoly P. Avdeenko Донбаська державна машинобудівна академія, Ukraine https://orcid.org/0000-0003-0549-2131
  • Igor Yu. Yakimenko ДВНЗ «Український державний хіміко-технологічний університет», Ukraine

DOI:

https://doi.org/10.15421/082026

Keywords:

benzamide, quinone imine, hydrochlorination, hydrobromination, thiocyanate addition, bioactivity, thiocyanate, addition of hydrogen halides.

Abstract

N-{3-[(Aryl-1-sulfonyl)imino]-6-oxocyclohexa-1,4-dienе-1-yl}benzamides have been synthesized by the reaction of the corresponding N-(4-oxocyclohexa-2,5-diene-1-ylidene)arylsulfonamides with N-chloramides with a ratio of reagents 1:2 in a solution of propan-2-one in the presence of triethylamine. The products of addition of hydrogen halides with the entry of halogen atoms in position 4 or 5 of the quinoid ring have been obtained as a result of hydrochlorination and hydrobromination of N-{3-[(aryl-1-sulfonyl)imino]-6-oxocyclohexa-1,4-diene-1-yl}benzamides. The possibility of hydrohalogenation and thiocyanation of these benzamides is determined by a steric factor. The presence of bulk substituents in the quinoid ring does not allow the introduction of a halogen atom in the 2 position of the quinoid ring. The product of aromatization of the quinoid cycle, N-{2-hydroxy-3,4-dimethyl-5-[(4-methylbenzene-1-sulfonyl)amino]phenyl}-4-methylbenzamide, was only obtained as a result of the action of hydrogen halides on 4-methyl-N-{4,5-dimethyl-3-[(4-methylbenzene-1-sulfonyl)imino]-6-oxocyclohexa-1,4-dienе-1-yl}benzamide. The thiocyanate ion addition product was obtained only for 4-chloro-N-{4-methyl-3-[(4-methylbenzene-1-sulfonyl)imino]-6-oxocyclohexa-1,4-dienе-1-yl}benzamide, which has a free ortho-position relative to the carbonyl carbon of the quinoid ring. The activities Insulysin inhibitor, CTGF expression inhibitor, Glutamyl endopeptidase II inhibitor, Transcription factor STAT3 inhibitor are possible for the products of hydrohalogenation and thiocyanation of N-{3-[(aryl-1-sulfonyl)imino]-6-oxocyclohexa-1,4-dienе-1-yl}benzamides.


Author Biographies

Svetlana A. Konovalova, Донбаська державна машинобудівна академія

Доцент кафедри хімії і охорони праці

Anatoly P. Avdeenko, Донбаська державна машинобудівна академія

Завідуючий кафедрою хімії і охорони праці

Igor Yu. Yakimenko, ДВНЗ «Український державний хіміко-технологічний університет»

Викладач кафедри фармації та технології органічних речовин

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Published

2021-01-10

Issue

Vol. 28 No. 3 (2020): Journal of Chemistry and Technologies

Section

Organic Chemistry

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