Utility of Fatty Wastes in Preparing Chemical intermediates and Evaluation of their Industrial Applications
Hayam Abd El Rahman Abd El Salaam;
Abstract
This invistigation deals with the utility of fatty wastes (produced as by-products of Egypt for Oils and Soap Company, Zagazig, Egypt) in the synthesis of new heterocycles linked to fatty acid residue which could be of potential biological and industrial applications this work is summarized in the following :
First: Facile synthesis of 6-heptadec-8-enyl thiopyrimidines incorporating glycosyl moiety and their antitumor activity.
The synthesis of 6-oleyl pyrimidine derivatives incorporating cyclic and acyclic sugar residue through S- or N-bond formation. In addition, 5-fluorouracil (5 FU) analogues containing oleyl moiety have been achieved. The new synthesized compounds were evaluated as antitumor agent.
Coupling of the aglycon (thio pyrimidine) 1 with sodium hydride in dry N, N-dimethylformamide followed by the addition of ((2,3,4,6-tetra-O-acetyl)-α-D-gluco- (or glacto) pyranosyl bromide) gave the corresponding thioglycoside derivatives 2a,b . Additionally, the reaction of 1 with β-chloroethoxyethanol and β-chloro diethylether in the presence of ethanolic KOH afforded thiopyrimidine derivatives 3a and 3b, respectively. (cf. Scheme1)
The oxidation of thiopyrimidine 1 by boiling in 10% chloroacetic acid gave uracil derivative 4 in a good yield. (cf. Scheme1)
The alkylation of thiopyrimidine 1 with methyl iodide, in the presence of potassium hydroxide, yielded 2- methyl thiopyrimidine derivative (5) which was subjected to react with 2,3,4,6-tetra-O-acetyl-α-D-gluco pyranosyl bromide in the presence of NaH in dry DMF to give the N1-6 nucleoside. (cf. Scheme 2)
Moreover, When compound 5 was reacted with the selected N-nucleophiles (pyrrolidine, morpholine, piperidine, or piperazine ) as a nitrogen base at fused temperature, the substituted pyrimidines 7a-d were obtained in good yield.
Also, the coupling of the aglycon 7a-d with 2,3,4,6-tetra-O-acetyl-α-D-gluco pyranosyl bromide in the presence of NaH in dry DMF gave the corresponding β-glycoside derivatives 8a-d in a good yield. (cf. Scheme 2)
Finally, the reaction of compounds 1, 4, or 7d with lithium fluoride was performed through catalytic substitution reaction using cerium(IV) ammonium nitrate (CAN) to afford the products 9a, 9b, and 10, respectively.(cf. Scheme3)
First: Facile synthesis of 6-heptadec-8-enyl thiopyrimidines incorporating glycosyl moiety and their antitumor activity.
The synthesis of 6-oleyl pyrimidine derivatives incorporating cyclic and acyclic sugar residue through S- or N-bond formation. In addition, 5-fluorouracil (5 FU) analogues containing oleyl moiety have been achieved. The new synthesized compounds were evaluated as antitumor agent.
Coupling of the aglycon (thio pyrimidine) 1 with sodium hydride in dry N, N-dimethylformamide followed by the addition of ((2,3,4,6-tetra-O-acetyl)-α-D-gluco- (or glacto) pyranosyl bromide) gave the corresponding thioglycoside derivatives 2a,b . Additionally, the reaction of 1 with β-chloroethoxyethanol and β-chloro diethylether in the presence of ethanolic KOH afforded thiopyrimidine derivatives 3a and 3b, respectively. (cf. Scheme1)
The oxidation of thiopyrimidine 1 by boiling in 10% chloroacetic acid gave uracil derivative 4 in a good yield. (cf. Scheme1)
The alkylation of thiopyrimidine 1 with methyl iodide, in the presence of potassium hydroxide, yielded 2- methyl thiopyrimidine derivative (5) which was subjected to react with 2,3,4,6-tetra-O-acetyl-α-D-gluco pyranosyl bromide in the presence of NaH in dry DMF to give the N1-6 nucleoside. (cf. Scheme 2)
Moreover, When compound 5 was reacted with the selected N-nucleophiles (pyrrolidine, morpholine, piperidine, or piperazine ) as a nitrogen base at fused temperature, the substituted pyrimidines 7a-d were obtained in good yield.
Also, the coupling of the aglycon 7a-d with 2,3,4,6-tetra-O-acetyl-α-D-gluco pyranosyl bromide in the presence of NaH in dry DMF gave the corresponding β-glycoside derivatives 8a-d in a good yield. (cf. Scheme 2)
Finally, the reaction of compounds 1, 4, or 7d with lithium fluoride was performed through catalytic substitution reaction using cerium(IV) ammonium nitrate (CAN) to afford the products 9a, 9b, and 10, respectively.(cf. Scheme3)
Other data
| Title | Utility of Fatty Wastes in Preparing Chemical intermediates and Evaluation of their Industrial Applications | Other Titles | استخدام المخلفات الدهنية في تحضير كيماويات وسيطة وتقييمها في التطبيقات الصناعية | Authors | Hayam Abd El Rahman Abd El Salaam | Issue Date | 2014 |
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