Synthesis of New Heterocyclic Compounds Via Nitrile group

number: 
1159
English
department: 
Degree: 
Author: 
Heba Adil Ali Al-Ukully
Supervisor: 
Dr. Sawsan H.Shawkat
year: 
2005

Preparation of new derivatives of heterocyclic compounds such as (Triazoles, teterazoles ,oxazoles,thiadiazoles,oxadiazoles and oxazolones) were the aim of this work .This work was achieved through the prepration of α- aminonitrile, which was prepared using amodified streck's procedure it incloud the reaction of amine (p-anisidine) with approprte aldehyde (benzaldehyde) followed by the addition potassium cyaide.The reaction was carried at PH(3-4) using glacial acetic acid as solvent.Hydrolysis of the α-aminonitrite with 90% sulpheric acid produse  α-aminoamide.Tetrazole was prepared from  α-aminonitrite  with sodium azide. α-aminoamide gave three different products (aminoacid , Oxazole and oxazolone ) when treated with concentrated HCl , p- bromophencyl bromide and chloro acetic acid respectively.Treatment of α-aminoacid with thionyl chloride under reflux for two hours yield the un acid chloride.When acid choride was refluxed with hydrazine hydrate, acid hydrazide was obtained.Potassium salt was obtained when acid hydrazide was mixed with KOH in absolute ethanol followed by the addition of carbon disulfide.

Triazole derivatives were obtained using three different starting compounds : potassium salt with hydrazine hydrate , thiosemicarbazide derivative with sodium hydroxide , and semicarbazide derivative with 10% potassium hydroxide.Thiodiazoles derivatives were obtained by mixing thiosemicarbazide comound with concentrated sulpheric acid.When acid hydrazide was refluxed with KOH followed by the addition carbon disulfide oxadiazole was obtained .Oxadiazole derivative was also obtained when semicarbazide  derivative was mixed with sulpheric acid.