The Novel route was developed for synthesis of high potential tetrazole carbamate and urea derivatives by using conventional methods. (trifluoromethyl)phenyl)quinoline-5-carboxamide (3) was converted into chloroamidine derivative by using POCl 3 and DMF (cat), then treated with sodium azide by [3+2] cycloaddition to give 8-(benzyloxy)-5-(1-(4-(trifluoromethyl) phenyl)-1H-tetrazol-5-yl)quinoline (5). The tetrazolidine compound was debenzylated, then Alkylation with Ethyl Bromo acetate and converted to acid (8) by hydrolysis with LiOH. The acid was converted to acid azide by using DPPA, and then Treated with Alcohols and Amine to give substituted Carbamates and urea derivatives by using Curtius rearrangement.
Keywords: Tetrazolidine; Diphenyl phosphoryl azide; [3+2]Cycloaddition reaction; Curties re-arrangement; Combi-flash chromatography
Objective of this ResearchPresent work is corresponding to develop novel synthetic route for preparation of the quinoline attached tetrazolidine urea and N-carbamate derivatives and characterized by IR and 1 H NMR.
The Mannich base of Thiozolidine-2,4-dione derivatives has come to lime light due to their various pharmacological activities. Thiazolidine-2,4-dione is an extensively explored heterocyclic nucleus for designing of novel agents implicated for a wide variety of pathophysiological conditions, that is, diabetes, diabetic complications, cancer, arthritis, inflammation, microbial infection, and melanoma. In present work, synthesis quinoline attached imidazoline derivative using (3 + 2) cyclo-addition via imine of quinoline and TosMIC. These derivatives were converted to Mannich bases of thiozolidine-2,4-dione using Knoevenagel condensation. The sulfonamide analogues of thiozolidine-2,4-Dione were also synthesized and characterized by using alkylation conditions.
The Novel route was developed for synthesis of high potential tetrazole carbamate and urea derivatives by using conventional methods. (trifluoromethyl)phenyl)quinoline-5-carboxamide (3) was converted into chloroamidine derivative by using POCl3 and DMF (cat), then treated with sodium azide by [3 + 2] cycloaddition to give 8-(benzyloxy)-5-(1-(4-(trifluoromethyl) phenyl)-1H-tetrazol-5-yl) quinoline (5). The tetrazolidine compound was debenzylated, then Alkylation with Ethyl Bromo acetate and converted to acid (8) by hydrolysis with LiOH. The acid was converted to acid azide by using DPPA, and then Treated with Alcohols and Amine to give substituted Carbamates and urea derivatives by using Curtius rearrangement.
The mannish bases of Thiozolidine 2,4 -dione derivatives has come to lime light due to their multi functional biological activities. Thiazolidine-2,4-dione is an extensively explored hetero cyclic nucleus for designing of novel agents implicated for a wide variety of pathophysiological conditions, that is, diabetes, diabetic complications ,cancer, arthritis, inflammation, microbial infection, and melanoma. Present work, synthesise quinoline attached imidozoline derivative using (3 +2) cycloaddition via imine of quinoline and TOSMIC. These derivatives were converted to mannich bases of thiozolidine 2,4 one using knoevenagel condensation. The sulfonyl derivatives of thiozolidine 2, 4 -dione were also synthesized and characterized by using alkylation conditions.
The Novel route was developed for synthesis of high potential tetrazole carbamate and urea derivatives by using conventional methods. (trifluoromethyl)phenyl)quinoline-5-carboxamide (3) was converted into chloroamidine derivative by using POCl3 and DMF (cat), then treated with sodium azide by [3+2] cycloaddition to give 8-(benzyloxy)-5-(1-(4-(trifluoromethyl)phenyl)-1H-tetrazol-5-yl) quinoline (5). The tetrazolidine compound was debenzylated, then Alkylation with Ethyl Bromo acetate and converted to acid (8) by hydrolysis with LiOH. The acid was converted to acid azide by using DPPA, and then Treated with Alcohols and Amine to give substituted Carbamates and urea derivatives by using Curtius rearrangement.
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