Synthesis of chalcones and derivatives

In the present study, we undertook the total synthesis of several chalcones and derivatives namely chalcone, 2’-hydroxychalcone, 2’,4-dihydroxychalcone, 2’- hydroxy -3,4-dimethoxychalcone, 1,3-diphenylprop-2-en-1-ol, 2,3-dibromochalcone, 1-(1,3-diphenylallylidene)-1-phenylhidrazine, 3-hydroxy-2-phen...

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Main Author:	Appu, Venothini
Format:	Thesis
Language:	English
Published:	2010
Subjects:	QD Chemistry
Online Access:	http://eprints.utm.my/id/eprint/11421/1/VenothiniAppuMFS2010.pdf
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id	my-utm-ep.11421
record_format	uketd_dc
spelling	my-utm-ep.114212018-05-30T02:49:05Z Synthesis of chalcones and derivatives 2010-04 Appu, Venothini QD Chemistry In the present study, we undertook the total synthesis of several chalcones and derivatives namely chalcone, 2’-hydroxychalcone, 2’,4-dihydroxychalcone, 2’- hydroxy -3,4-dimethoxychalcone, 1,3-diphenylprop-2-en-1-ol, 2,3-dibromochalcone, 1-(1,3-diphenylallylidene)-1-phenylhidrazine, 3-hydroxy-2-phenyl-4-chromen-4-one and 2-phenylchromen-4-one. These target compounds were synthesized via Claisen- Schmidt condensation of the respective ketones and benzaldehydes under basic condition to give the corresponding chalcone, 2’-hydroxychalcone, and 2’-hydroxy - 3,4-dimethoxychalcone. At the same time, 2’,4-dihydroxychalcone was synthesized by Boron-trifluoride etherate method. 2’-Hydroxychalcone was converted to flavone by treatment with iodine in dimethylsulfoxide and to 3-hydroxy-2-phenyl-4- chromen-4-one by treating with hydrogen peroxide and NaOH. 1,3-Diphenylprop-2- en-1-ol was synthesized from chalcone through reduction process using NaBH4 while 1-(1,3-diphenylallylidene)-1-phenylhidrazine was prepared from chalcone and phenylhydrazine in ethanol. Structures were confirmed spectroscopically by IR, NMR (1H and 13C), DEPT and GC-MS. The antibacterial and toxicity activities of the synthesized compounds were evaluated by disc diffusion method and brine shrimps lethality test, respectively. All the synthesized compounds were inactive towards the tested bacteria. Chalcone and 2’-hydroxychalcone were found to be the most toxic compounds against brine shrimp (Artemia salina) both with LD50 1.7 ppm. 2010-04 Thesis http://eprints.utm.my/id/eprint/11421/ http://eprints.utm.my/id/eprint/11421/1/VenothiniAppuMFS2010.pdf application/pdf en public masters Universiti Teknologi Malaysia, Faculty of Science Faculty of Science
institution	Universiti Teknologi Malaysia
collection	UTM Institutional Repository
language	English
topic	QD Chemistry
spellingShingle	QD Chemistry Appu, Venothini Synthesis of chalcones and derivatives
description	In the present study, we undertook the total synthesis of several chalcones and derivatives namely chalcone, 2’-hydroxychalcone, 2’,4-dihydroxychalcone, 2’- hydroxy -3,4-dimethoxychalcone, 1,3-diphenylprop-2-en-1-ol, 2,3-dibromochalcone, 1-(1,3-diphenylallylidene)-1-phenylhidrazine, 3-hydroxy-2-phenyl-4-chromen-4-one and 2-phenylchromen-4-one. These target compounds were synthesized via Claisen- Schmidt condensation of the respective ketones and benzaldehydes under basic condition to give the corresponding chalcone, 2’-hydroxychalcone, and 2’-hydroxy - 3,4-dimethoxychalcone. At the same time, 2’,4-dihydroxychalcone was synthesized by Boron-trifluoride etherate method. 2’-Hydroxychalcone was converted to flavone by treatment with iodine in dimethylsulfoxide and to 3-hydroxy-2-phenyl-4- chromen-4-one by treating with hydrogen peroxide and NaOH. 1,3-Diphenylprop-2- en-1-ol was synthesized from chalcone through reduction process using NaBH4 while 1-(1,3-diphenylallylidene)-1-phenylhidrazine was prepared from chalcone and phenylhydrazine in ethanol. Structures were confirmed spectroscopically by IR, NMR (1H and 13C), DEPT and GC-MS. The antibacterial and toxicity activities of the synthesized compounds were evaluated by disc diffusion method and brine shrimps lethality test, respectively. All the synthesized compounds were inactive towards the tested bacteria. Chalcone and 2’-hydroxychalcone were found to be the most toxic compounds against brine shrimp (Artemia salina) both with LD50 1.7 ppm.
format	Thesis
qualification_level	Master's degree
author	Appu, Venothini
author_facet	Appu, Venothini
author_sort	Appu, Venothini
title	Synthesis of chalcones and derivatives
title_short	Synthesis of chalcones and derivatives
title_full	Synthesis of chalcones and derivatives
title_fullStr	Synthesis of chalcones and derivatives
title_full_unstemmed	Synthesis of chalcones and derivatives
title_sort	synthesis of chalcones and derivatives
granting_institution	Universiti Teknologi Malaysia, Faculty of Science
granting_department	Faculty of Science
publishDate	2010
url	http://eprints.utm.my/id/eprint/11421/1/VenothiniAppuMFS2010.pdf
_version_	1747814852961763328

Synthesis of chalcones and derivatives

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