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» تحضير بعض المركبات الحلقية غير المتجانسة الجديدة المشتقة من N - الكيل -C بنزسلفونأميد- Synthesis of some new heterocyclic compounds derived from N-alkyl (2-carboxy) benzsulfonamide
تحضير بعض المركبات الحلقية غير المتجانسة الجديدة المشتقة من N - الكيل -C بنزسلفونأميد- Synthesis of some new heterocyclic compounds derived from N-alkyl (2-carboxy) benzsulfonamide
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تحضير بعض المركبات الحلقية غير المتجانسة الجديدة المشتقة من N - الكيل -C بنزسلفونأميد
Synthesis of some new heterocyclic compounds derived from N-alkyl (2-carboxy) benzsulfonamide
لـ : علي رياض محمد حسين
ماجستير في علوم الكيمياء
جامعة بغداد - كلية العلوم 2015
:
Abstract
Throughout this
work, some of new sulfonamide derivatives have been
synthesized
from sodium saccharin as a starting material. This work is
divided into
three parts: the steps for each part are summarized as shown
below:-
Part (1) :(
Scheme 1)
This part
involves:
1)- Synthesis
of N-alkyl saccharin derivatives (1a-b) via reaction of
sodium
saccharin salt with some alkyl halides, such as benzyl chloride
and n-propyl
bromide.
2)- Hydrolysis
of N-alkyl saccharin derivatives using 5%NaOH to get carboxylic acid derivatives (2a-b).
3)- Synthesis
of ester derivatives (3a-b) via the reaction of the carboxylic
acid
derivatives (2a-b) with an absolute ethanol in the presence of concentrated sulfuric
acid.
4)-Synthesis
of 2-benzohyrazino sulfonamide derivatives (4a-b) via the
reaction of
ester derivatives (3a-b) with 80% hydrazine hydrate.
Part (2)
(Scheme 2):-
This part
includes:
1) - Synthesis
of 3-mercapto-4-amino-1, 2, 4-triazole-5-benzsulfonamide
derivatives
(5a-b) by reaction of 2-benzohydrazino sulfonamide
derivatives
with carbon disulfide in the presence of potassium hydroxide,
and 80%
hydrazine hydrate.
2)-Synthesis
of 6-mercapto-1, 2, 4-triazole-5-yl) (3,4-b) (1,3,4-thiadizole)
(6a-b) by
reaction of (5a-b) with carbon disulfide in the presence of
potassium
hydroxide.
3)-Synthesis
of Schiff base(7a-d) via the condensation of compounds (5ab)
with some
aromatic aldehydes, such as 4-dimethylaminobenzaldehyde
and
2,4-dimethoxybenzaldehyde in the presence of few drops of glacial
acetic acid.
4)-Synthesis
of 3-mercapto-1, 2, 4-triazole-5-benz sulfonamide derivatives (8a-b) via the fusion of
compounds (4a-b) with ammonium thiocyanate.
5)-Synthesis
of 2[-5-oxo-5,6-di hydro thiazole (3,2-b)-1,2,4-triazole]-Nalkyl
benzsulfamido
derivatives (9a-b) from the cyclization of (8a-b) with chloro acetic acid and anhydrous Sodium
acetate .
6)-Synthesis
of 2-[3-hydroxy-4-phenyl-1, 2, 4-triazole]-N-alkyl benzsulfonamide derivatives (11a-b) by
reaction new 2-[N\-phenyl hydrazine
carboxamide]-N-benzyl benzsulfamido derivatives (10a-b) with 30% (NaOH)
Part (3)
(Scheme 3):
This part
involves:
1)-Synthesis
of 2-acid-[N-(2-amino-1,3-thiozole-5-yl)]hydrazide-Nalkyl
benzsulfonamide
(13a-b) from the cyclization of new 2-acid
(N-chloroacetyl)
hydrazide-N-alkyl benzsulfamido derivatives ( (12a-b)
with thiourea.
2) - Synthesis
of Schiff bases (14a-b) via the condensation of (13a-b) with
some aromatic
aldehydes such as 4-dimethylaminobenzaldehyde and
2,
4-dimethoxybenzaldehyde in the presence of few drops of glacial
acetic acid.
3) - Synthesis
of Schiff bases (15a-f) via the condensation of (4a-b) with
some aromatic
aldehydes such as 4-methoxy benzaldehyde 4-bromo
benzaldehyde
and 2-hyderoxy benzaldehyde in the presence of few drops
of glacial
acetic acid.
4)- synthesis
of 1,3- diazetidine-2-one (Aza--Lactam)
derivatives (16af),
from the
cyclization of new Schiff- base derivatives (15a-f) with
phenylisocynide. The newly prepared
compounds have been identified by FTIR, 13C-NMR and 1HNMR
spectra.
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