Studies on Synthesis of Some Novel Heterocyclic Chalcone, Pyrazoline, Pyrimidine - 2 - One, Pyrimidine - 2 - Thione, para-Acetanilide Sulphonyl and Benzoyl Derivatives and their Antimicrobial Activity

1, 2 - Dichloro benzene on chlorosulphonation by chlorosulphonic acid gives 1, 2 - [dichloro] - benzene sulphonyl chloride which on condensation with p –amino acetophenone gives 1-[acetyl] - 1’ , 2’ - [dichloro] - dibenz sulphonamide de...

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Main Authors: Rakesh N. Mistry, K. R. Desai
Format: Article
Language:English
Published: Wiley 2005-01-01
Series:E-Journal of Chemistry
Online Access:http://dx.doi.org/10.1155/2005/953107
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author Rakesh N. Mistry
K. R. Desai
author_facet Rakesh N. Mistry
K. R. Desai
author_sort Rakesh N. Mistry
collection DOAJ
description 1, 2 - Dichloro benzene on chlorosulphonation by chlorosulphonic acid gives 1, 2 - [dichloro] - benzene sulphonyl chloride which on condensation with p –amino acetophenone gives 1-[acetyl] - 1’ , 2’ - [dichloro] - dibenz sulphonamide derivative. This derivative undergo condensation with 2,4- dichloro benzaldehyde gives 1- [3” - (sub. phenyl) - 2” - propene - 1” - one] - 1’ , 2’ - [dichloro] - dibenz sulphonamide derivative which on reaction with 99% hydrazine hydrate and glacial acetic acid gives 1-[acetyl]-3- [1’ , 2’ - (dichloro) - dibenz sulphonamide] -5 - [2” , 4” - dichloro phenyl] - 2 - pyrazoline derivative. This derivative reacts with various substituted aldehydes to give corresponding substituted chalcone derivatives [1(a-j)]. Now, these chalcone derivatives [1(a-j)] on condensation with urea gives corresponding substituted pyrimidine - 2 - one derivatives [2(a-j)] and on condensation with thio-urea gives corresponding substituted pyrimidine- 2 -thione derivatives [3(a-j)]. Further, these chalcone derivatives [1(a-j)] on reaction with 99% hydrazine hydrate gives 1 - [1’ - (H) - 5’ - (sub. phenyl) - 2’ - pyrazoline]- 3 - [1” , 2” - (dichloro) - dibenz sulphonamide] - 5 - [2’’’ , 4’’’ - dichloro phenyl]-2- pyrazoline derivatives [4(a-j)] as an intermediate compounds, which on condensation with p-acetanilide sulphonyl chloride gives corresponding substituted p - acetanilide sulphonyl derivatives [5(a-j)] and on condensation with benzoyl chloride gives corresponding substituted benzoyl derivatives [6(a-j)]. Structure elucidation of synthesised compounds has been made on the basis of elemental analysis, I.R. spectral studies and 1H N.M.R. spectral studies. The antimicrobial activity of the synthesised compounds has been studied against the cultures “Staphylococcus aureus”, “Escherichia coli” and “Candela albicans”.
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spelling doaj-art-74eb6a1ce25a4b53b6887d0a775849d62025-02-03T05:50:14ZengWileyE-Journal of Chemistry0973-49452090-98102005-01-0121304110.1155/2005/953107Studies on Synthesis of Some Novel Heterocyclic Chalcone, Pyrazoline, Pyrimidine - 2 - One, Pyrimidine - 2 - Thione, para-Acetanilide Sulphonyl and Benzoyl Derivatives and their Antimicrobial ActivityRakesh N. Mistry0K. R. Desai1Department of Chemistry, Veer Narmad South Gujarat University, Surat-395 007, IndiaDepartment of Chemistry, Veer Narmad South Gujarat University, Surat-395 007, India1, 2 - Dichloro benzene on chlorosulphonation by chlorosulphonic acid gives 1, 2 - [dichloro] - benzene sulphonyl chloride which on condensation with p –amino acetophenone gives 1-[acetyl] - 1’ , 2’ - [dichloro] - dibenz sulphonamide derivative. This derivative undergo condensation with 2,4- dichloro benzaldehyde gives 1- [3” - (sub. phenyl) - 2” - propene - 1” - one] - 1’ , 2’ - [dichloro] - dibenz sulphonamide derivative which on reaction with 99% hydrazine hydrate and glacial acetic acid gives 1-[acetyl]-3- [1’ , 2’ - (dichloro) - dibenz sulphonamide] -5 - [2” , 4” - dichloro phenyl] - 2 - pyrazoline derivative. This derivative reacts with various substituted aldehydes to give corresponding substituted chalcone derivatives [1(a-j)]. Now, these chalcone derivatives [1(a-j)] on condensation with urea gives corresponding substituted pyrimidine - 2 - one derivatives [2(a-j)] and on condensation with thio-urea gives corresponding substituted pyrimidine- 2 -thione derivatives [3(a-j)]. Further, these chalcone derivatives [1(a-j)] on reaction with 99% hydrazine hydrate gives 1 - [1’ - (H) - 5’ - (sub. phenyl) - 2’ - pyrazoline]- 3 - [1” , 2” - (dichloro) - dibenz sulphonamide] - 5 - [2’’’ , 4’’’ - dichloro phenyl]-2- pyrazoline derivatives [4(a-j)] as an intermediate compounds, which on condensation with p-acetanilide sulphonyl chloride gives corresponding substituted p - acetanilide sulphonyl derivatives [5(a-j)] and on condensation with benzoyl chloride gives corresponding substituted benzoyl derivatives [6(a-j)]. Structure elucidation of synthesised compounds has been made on the basis of elemental analysis, I.R. spectral studies and 1H N.M.R. spectral studies. The antimicrobial activity of the synthesised compounds has been studied against the cultures “Staphylococcus aureus”, “Escherichia coli” and “Candela albicans”.http://dx.doi.org/10.1155/2005/953107
spellingShingle Rakesh N. Mistry
K. R. Desai
Studies on Synthesis of Some Novel Heterocyclic Chalcone, Pyrazoline, Pyrimidine - 2 - One, Pyrimidine - 2 - Thione, para-Acetanilide Sulphonyl and Benzoyl Derivatives and their Antimicrobial Activity
E-Journal of Chemistry
title Studies on Synthesis of Some Novel Heterocyclic Chalcone, Pyrazoline, Pyrimidine - 2 - One, Pyrimidine - 2 - Thione, para-Acetanilide Sulphonyl and Benzoyl Derivatives and their Antimicrobial Activity
title_full Studies on Synthesis of Some Novel Heterocyclic Chalcone, Pyrazoline, Pyrimidine - 2 - One, Pyrimidine - 2 - Thione, para-Acetanilide Sulphonyl and Benzoyl Derivatives and their Antimicrobial Activity
title_fullStr Studies on Synthesis of Some Novel Heterocyclic Chalcone, Pyrazoline, Pyrimidine - 2 - One, Pyrimidine - 2 - Thione, para-Acetanilide Sulphonyl and Benzoyl Derivatives and their Antimicrobial Activity
title_full_unstemmed Studies on Synthesis of Some Novel Heterocyclic Chalcone, Pyrazoline, Pyrimidine - 2 - One, Pyrimidine - 2 - Thione, para-Acetanilide Sulphonyl and Benzoyl Derivatives and their Antimicrobial Activity
title_short Studies on Synthesis of Some Novel Heterocyclic Chalcone, Pyrazoline, Pyrimidine - 2 - One, Pyrimidine - 2 - Thione, para-Acetanilide Sulphonyl and Benzoyl Derivatives and their Antimicrobial Activity
title_sort studies on synthesis of some novel heterocyclic chalcone pyrazoline pyrimidine 2 one pyrimidine 2 thione para acetanilide sulphonyl and benzoyl derivatives and their antimicrobial activity
url http://dx.doi.org/10.1155/2005/953107
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AT krdesai studiesonsynthesisofsomenovelheterocyclicchalconepyrazolinepyrimidine2onepyrimidine2thioneparaacetanilidesulphonylandbenzoylderivativesandtheirantimicrobialactivity