PURINES, PYRIMIDINES, AND IMIDAZOLES .58. SYNTHESIS AND REACTIONS OF SOME IMIDAZOLE-2,4-DICARBOXYLIC ACID-DERIVATIVES
Diethyl 5-amino-1-(p-methoxybenzyl)imidazole-2,4-dicarboxylate (3b) has been prepared from ethyl 2-amino-2-cyanoacetate and ethyl 1- ethoxycarbonyformimidate hydrochloride or ethyl triethoxyacetate followed by reaction with p-methoxybenzy lamine. The diester, with one equivalent of dilute sodium hyd...
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| Format: | Journal article |
| Language: | English |
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1983
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| _version_ | 1826287315751796736 |
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| author | Brown, T Shaw, G Durant, G |
| author_facet | Brown, T Shaw, G Durant, G |
| author_sort | Brown, T |
| collection | OXFORD |
| description | Diethyl 5-amino-1-(p-methoxybenzyl)imidazole-2,4-dicarboxylate (3b) has been prepared from ethyl 2-amino-2-cyanoacetate and ethyl 1- ethoxycarbonyformimidate hydrochloride or ethyl triethoxyacetate followed by reaction with p-methoxybenzy lamine. The diester, with one equivalent of dilute sodium hydroxide solution, furnished ethyl 5-amino-1-(p-methoxybenzyl)imidazole- 4-carboxylate (7a). Diazotisation of the diester (3b) and reaction of the diazonium salt with copper(I) chloride produced diethyl 5-chloro-1-(p- methoxybenzyl)imidazole-2,4-dicarboxylate (9a) which, with dilute alkali, gave ethyl 5-chloro-1-(p-methoxybenzyl)imidazole-4-carboxylate (7b). Diazotisation of the diester (3b) in the presence of hypophosphorous acid gave diethyl-1-(p-methoxybenzyl)imidazole-2,4-carboxylate (9b) which, when hydrogenated over palladium - charcoal, produced diethyl imidazole-2,4- dicarboxylate (9c). This with bromine (chlorine) gave diethyl 5-bromo(chloro)imidazole-2,4-dicarboxylate (9d and e). The chloro derivative (9a) was similarly hydrogenated using palladium - charcoal to produce diethyl 5-chloro-imidazole-2,4-dicarboxylate (9e). |
| first_indexed | 2024-03-07T01:56:50Z |
| format | Journal article |
| id | oxford-uuid:9bfb8cec-4422-4ce8-881b-07de44398ac3 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T01:56:50Z |
| publishDate | 1983 |
| record_format | dspace |
| spelling | oxford-uuid:9bfb8cec-4422-4ce8-881b-07de44398ac32022-03-27T00:33:00ZPURINES, PYRIMIDINES, AND IMIDAZOLES .58. SYNTHESIS AND REACTIONS OF SOME IMIDAZOLE-2,4-DICARBOXYLIC ACID-DERIVATIVESJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:9bfb8cec-4422-4ce8-881b-07de44398ac3EnglishSymplectic Elements at Oxford1983Brown, TShaw, GDurant, GDiethyl 5-amino-1-(p-methoxybenzyl)imidazole-2,4-dicarboxylate (3b) has been prepared from ethyl 2-amino-2-cyanoacetate and ethyl 1- ethoxycarbonyformimidate hydrochloride or ethyl triethoxyacetate followed by reaction with p-methoxybenzy lamine. The diester, with one equivalent of dilute sodium hydroxide solution, furnished ethyl 5-amino-1-(p-methoxybenzyl)imidazole- 4-carboxylate (7a). Diazotisation of the diester (3b) and reaction of the diazonium salt with copper(I) chloride produced diethyl 5-chloro-1-(p- methoxybenzyl)imidazole-2,4-dicarboxylate (9a) which, with dilute alkali, gave ethyl 5-chloro-1-(p-methoxybenzyl)imidazole-4-carboxylate (7b). Diazotisation of the diester (3b) in the presence of hypophosphorous acid gave diethyl-1-(p-methoxybenzyl)imidazole-2,4-carboxylate (9b) which, when hydrogenated over palladium - charcoal, produced diethyl imidazole-2,4- dicarboxylate (9c). This with bromine (chlorine) gave diethyl 5-bromo(chloro)imidazole-2,4-dicarboxylate (9d and e). The chloro derivative (9a) was similarly hydrogenated using palladium - charcoal to produce diethyl 5-chloro-imidazole-2,4-dicarboxylate (9e). |
| spellingShingle | Brown, T Shaw, G Durant, G PURINES, PYRIMIDINES, AND IMIDAZOLES .58. SYNTHESIS AND REACTIONS OF SOME IMIDAZOLE-2,4-DICARBOXYLIC ACID-DERIVATIVES |
| title | PURINES, PYRIMIDINES, AND IMIDAZOLES .58. SYNTHESIS AND REACTIONS OF SOME IMIDAZOLE-2,4-DICARBOXYLIC ACID-DERIVATIVES |
| title_full | PURINES, PYRIMIDINES, AND IMIDAZOLES .58. SYNTHESIS AND REACTIONS OF SOME IMIDAZOLE-2,4-DICARBOXYLIC ACID-DERIVATIVES |
| title_fullStr | PURINES, PYRIMIDINES, AND IMIDAZOLES .58. SYNTHESIS AND REACTIONS OF SOME IMIDAZOLE-2,4-DICARBOXYLIC ACID-DERIVATIVES |
| title_full_unstemmed | PURINES, PYRIMIDINES, AND IMIDAZOLES .58. SYNTHESIS AND REACTIONS OF SOME IMIDAZOLE-2,4-DICARBOXYLIC ACID-DERIVATIVES |
| title_short | PURINES, PYRIMIDINES, AND IMIDAZOLES .58. SYNTHESIS AND REACTIONS OF SOME IMIDAZOLE-2,4-DICARBOXYLIC ACID-DERIVATIVES |
| title_sort | purines pyrimidines and imidazoles 58 synthesis and reactions of some imidazole 2 4 dicarboxylic acid derivatives |
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