Synthesis of New Imidazolidine and Tetrahydropyrimidine Derivatives (original) (raw)
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2015
Synthesis of N-(2-(4-substituted phenyl)-3-(2-(1,3-dioxoisoindolin-2-yloxy)ethyl)-5-oxoimidazolidin-1-yl)-3-(2-(1,3dioxoisoindolin-2-yloxy)ethyl)-6-methyl-2-oxo/thioxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamides and N-(2-(4substituted phenyl)-3-(2-(1,3-dioxo-2,3-dihydro-1H-inden-2-yloxy)ethyl)-5-oxoimidazolidin-1-yl)-7-methyl-3-oxo-5phenyl-3,5-dihydro-2H-oxazolo/thiazolo[3,2-a]pyrimidine-6-carboxamides are described in the present investigation by multistep reactions via common intermediate. 6-methyl-2-oxo/thioxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate have been prepared by three component Beginelli reaction between benzaldeyde, urea/thiourea and ethyl acetoacetate which is further converted to carbohydrazide derivatives by treating it with hydrazine hydrate. Condensation of with various araldehydes produces the key intermediate N-(4-substituted benzylidene)-6-methyl-2-oxo/thioxo-4-phenyl-1,2,3,4tetrahydropyrimidine-5-carbohydrazides. Reactions towards route (A)...
2015
117-127Synthesis of N-(2-(4-substituted phenyl)-3-(2-(1,3-dioxoisoindolin-2-yloxy)ethyl)-5-oxoimidazolidin-1-yl)-3-(2-(1,3-dioxoisoindolin-2-yloxy)ethyl)-6-methyl-2-oxo/thioxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamides and N-(2-(4-substituted phenyl)-3-(2-(1,3-dioxo-2,3-dihydro-1H-inden-2-yloxy)ethyl)-5-oxoimidazolidin-1-yl)-7-methyl-3-oxo-5-phenyl-3,5-dihydro-2H-oxazolo/thiazolo[3,2-a]pyrimidine-6-carboxamides are described in the present investigation by multistep reactions via common intermediate. 6-methyl-2-oxo/thioxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate have been prepared by three component Beginelli reaction between benzaldeyde, urea/thiourea and ethyl acetoacetate which is further converted to carbohydrazide derivatives by treating it with hydrazine hydrate. Condensation of with various araldehydes produces the key intermediate N-(4-substituted benzylidene)-6-methyl-2-oxo/thioxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carbohydrazides. Reactions toward...
European Journal of Medicinal Chemistry, 2009
Fifty-one acylthioureas (ATUs) incorporating imidazolidine-2-thione or its upper cyclohomologue were prepared by parallel synthesis and evaluated against a high number of human cancer cell lines for antiproliferative activity. ATUs 1o (3,5-dichlorobenzoyl), 1s (2-furoyl), 3s (2-furoyl) and 1t (2-thenoyl) displayed activity against leukemia, melanoma LOX IMVI, non-small cell lung NCI-H522, renal 786-0, CAKI-1, SN12C, UO-31 and breast MCF7, MDA-MB-435, T-47D cancer cell lines in the 0.3e9.7 mM concentration range. Compound 14s exhibited selectivity for melanoma SK-MEL-5 (GI 50 < 5 nM); 1s for leukemia MOLT-4 (GI 50 : 300 nM); 1q, 3b and 3q for renal cancer UO-31 (GI 50 : 70e 200 nM); 8s, 9s for non-small cell lung cancer EKVX (GI 50 : 300, 10 nM) and 3j for HOP-92 (GI 50 : 700 nM) cell line.
Journal of Heterocyclic Chemistry, 2001
Triazapentadienium iodides 2 prepared from N'-thiocarbamoylformamidines 1 are efficient intermediates in heterocyclic synthesis. They react with ketenes, sulfenes, phenyl isocyanate or isothiocyanate and dimethyl acetylenedicarboxylate affording the corresponding dihydropyrimidinones 3, thiadiazinedioxides 5, triazinones 6, triazinethiones 7 and pyrimidines 9. J. Heterocyclic Chem., 38, 93 (2001).
Design, Synthesis and Characterization of Pyrimidine based Thiazolidinedione Derivatives
Asian Journal of Chemistry, 2020
Novel thiazolidine-2,4-dione (TZD) based pyrimidine derivatives have been synthesized by Knoevenagel condensation reaction between thiazolidine-2,4-dione and amino pyrimidinyl aliphatic aldehydes followed by heterogeneous metal reduction. Synthetic strategy involved nucleophillic substitution of hydroxyl protected six membered aliphatic chain on 4,6-dichloropyrimidine followed by Suzuki coupling. This approach is regioselective, efficient and versatile for synthesis of such analogs
Synthesis of potential pharmaceutically active dihydropyrimidine-2-oxo and their 2-thio analogues
Bangladesh Journal of Scientific and Industrial Research
The Biginelli one - pot three-component cyclocondensation was applied to prepare 3, 4 - dihydropyrimidin - 2 (1H) – ones from aldehydes, β-dicarbonyl compounds and urea (or thiourea) using ZnCl2 as a catalyst. The method offers several advantages including short reaction times and easy experimental work up procedures.Bangladesh J. Sci. Ind. Res.53(4), 327-332, 2018
Molecules, 2009
Hydantoins and their derivatives constitute a group of pharmaceutical compounds with anticonvulsant and antiarrhythmic properties, and are also used against diabetes. N-3 and C-5 substituted imidazolidines are examples of such products. As such, we have developed a synthesis of 2,4-dione and 2-thioxo-4-one imidazolidinic derivatives by reaction of amino acids with C-phenylglycine, phenyl isocyanate and phenyl isothiocyanate. Four amino-derivatives IG(1-4) and eight imidazolidinic derivatives, IM(1-8), were obtained in yields of 70-74%. The mass, infrared, 1 H and 13 C-NMR spectra of representative products are discussed.