Search In this Thesis
   Search In this Thesis  
العنوان
Uses of organic azides in organic synthesis /
المؤلف
Abdel Aziz, Amr El said.
هيئة الاعداد
باحث / amr elsaid abd elaziz
مشرف / a.i elshenawy
مشرف / s.a nassa
مناقش / m.m. h arief
مناقش / ,s.a essawy
الموضوع
Organic chemistry.
تاريخ النشر
2006 .
عدد الصفحات
127 p. :
اللغة
الإنجليزية
الدرجة
ماجستير
التخصص
الكيمياء
تاريخ الإجازة
1/1/2006
مكان الإجازة
جامعة بنها - كلية العلوم - كمياء
الفهرس
Only 14 pages are availabe for public view

from 166

from 166

Abstract

4-(p-Methoxy-benzylidene) 2-phenyl-I-irnidazolono -acetic acid
azide (3a) and 4-(p-methoxy-benzylidene) 2-(p-methoxy-phenyl )-1-
imidazolono-acetic acid azide ( 3b ) were newly prepared from the
corresponding acid chlorides. Imidazolone which is a part of the azides
have been found to be associated with several pharmacological
activities(l75.178) as well as the herbicidical activities of diaryl ureas(179),so
it is planed to study the biological activity of some of the synthesized
compounds.
The present investigation deals with the preparation of organic
compound via the decomposition reactions of azides ( 3 a&b) under
different conditions ( base- , acid- and neutral-catalyzed decomposition ).
Azides (3a and lor 3b) underwent base catalyzed decomposition
with aromatic amines to give the corresponding anilides ( 4a - f) via azido
group displacement. However azides (3a and/or 3b) underwent base
catalyzed decomposition with amino benzoic acids to give the
corresponding ureas derivatives (5 a - d) via Curtius rearrangement .On
the o.ther hand catalyzed decomposition of azide ( 3a ) with hydrazines
which and aroyl hydrazins gave the corresponding hydrazides (8 a,b) and
aroyl hydrazides ( 8c-e ) respectively via azido group . When aroyl
hydrazides (8c-e) were refluxed in acetic anhydride it was easily
cyclized to the corresponding oxadiazole derivatives (9 a-c ). However
azide (3b) underwent base-cataIyzed decomposition with hydrazine
hydrate and lor phenyl hydrazine to give the corresponding semicarbazides
( lOa and lOb ) via Curtius rearrangement.
Decomposition of azides ( 3a and lor 3b) with glycine gave
oxazolinone derivatives ( 12a and 12b ) respectively, via azido group
displacement.
Decomposition of azides ( 3 a&b ) in neutral midium ( water) gave
the corresponding sym, diaryl ureas ( 13a and I3b ) via Curtius
rearrangement.
Lewis acid - catalyzed decomposition of azide (3a ) with anhydrous
AICh in benzene gave methylamino-N-benzoyl derivatives ( 14 ) via
Curtius rearrangement .On the other hand azide (3b )under Lewis acidcatalyzed
decomposition of azide ( 3b) with anhydrous AICh in benzene
to give the corresponding ketone ( 15 ) via azido group displacement.
Acid chloride ( 2a ) underwent internal Friedel Craft reaction in the
presence of anhydrous AICh in tetra chloro-ethane to give isquinolin
derivative ( 16 ) .Also acid chloride ( 2a ) reacted with ammonium
thiocyanate in dry acetone to give isothiocyanate derivative ( 17) which
when treated with arylidene - arylamine it gave the corresponding
oxadiazine thione derivatives ( 18 a - c ).
Some of the synthesized compounds were tested toward(Bacillus
subtilis, Bacillus megaterium, Aspergillus sp. and Penicillium sp. ) .
The structure of the synthesized compounds were proved by infrared
spectra and elemental analysis in Cairo University . Mass spectra and
J H.N.M.R of the some synthesized compound were also investigated.