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العنوان
The Use of α,β-Unsaturated Carbonyl Compounds in the Preparation of some New Fused Heterocyclic
Compounds
المؤلف
Mahmoud Elsaid Ali,Fatma Elzahraa
هيئة الاعداد
باحث / Fatma Elzahraa Mahmoud Elsaid Ali
مشرف / Galal Hosni Sayed
مشرف / Mohamed Said Abd ElHalim
مشرف / Magdy Mohamed Hemdan
الموضوع
PREPARATIONS & REACTIONS OF <br>α, β –UNSATURATED CARBONYL COMPOUNDS<br>-
تاريخ النشر
2010.
عدد الصفحات
199.p:
اللغة
الإنجليزية
الدرجة
ماجستير
التخصص
Organic Chemistry
تاريخ الإجازة
10/5/2010
مكان الإجازة
جامعة عين شمس - كلية العلوم - Organic Chemistry
الفهرس
Only 14 pages are availabe for public view

from 188

from 188

Abstract

α,β –Unsaturated carbonyl compounds (α-enones) are versatile reagents and their chemistry have considerable interest .They form the central core for a variety of important biological compounds .They show antibacterial ,antifungal,antitumer and anti-inflammatory properties. They are also intermediates in the biosynthesis of flavonoids, which are substances widespread in plants and with an array of biological activates. Morevor ,it was found that they decrease the corrosion rates of steel. This draws our attention to utilize(α-enones) as starting materials to synthesis fused heterocyclic ring systems as well as to use them as dienes in Diles-Alder reaction with different dienophiles.
Thus, our work in this thesis is presented in two parts
Part I:
The utility of 2,6-bis (3-phenylallyidine)cyclohexanone (1a) and /or 2,6 bis (furane-2-ylmethylene)cyclohexanone (1b) in synthesis of some new fused heterocyclic ring systems like, indazole, thiazine, chromene and quinoline derivatives bearing styryl and 2-furyl moieties hoping to enhance their biological activities
Thus α-enones 1a and 1b reacted additively with hydrazine hydrate, thiourea, diethyl malonate, malononitrile, as well as ethyl cyanoacetate .Simultaneous cyclization of the resulting 1:1 adducts yields indazole 2-4, thiazine 6a,b chromene 7a-c and quinoline 8a,b derivatives .The structures of all the synthesized compounds were confirmed by micro analytical and spectral data. The antimicrobial activity of some of the synthesized compounds was tested
Part II:
The aim of this part is to study thermal {µ4s + µ2s }Diels_ Alder reaction for compounds la and /or lb as with different dienophiles
( µ2s components ) the reactions of compounds 1a and/or 1b with the different dienophiles were achieved under both conventional and microwave heating
The main target of this study is the synthesis of 2:1 new adducts as dispiro compounds
Thus reaction of a solution 1a in dry toluene with diethyl acetylene dicarboxylate 3-(3- nitrophenyl)- l -phenylprop-2-en-1-one, malic anhydiride and/or N-phenylmalimide afforded dispiro compounds 9-12. However reactions of 1b with cinnamic acid,1-buten-3-one,3-(3-nitrophenyl)-1-phenyl prop-2-en-1-one, vinylacetic acid and/or maleic anhydride produced adducts 13-17
On the other hand ,the reactions of 1a and/or 1b with the above specified dienophiles under microwave heating furnished the same products 9-12 and 13-17 respectively in few minutes.
The structure of the new compounds were cofirmed by their micro analytical and spectral data. The antimicrobial activities of some of the synthesized compounds were tested