PURINES, PYRIMIDINES, AND IMIDAZOLES .53. SYNTHESIS OF SOME 5-HALOGENO-ANALOGUES OF METIAMIDE AND CIMETIDINE
Ethyl 5-chloroimidazole-4-carboxylate has been prepared by diazotisation of ethyl 5-amino-1-(di-O-isopropylidene-α- or -α,β-D- mannofuranosyl)imidazole-4-carboxylate, reaction of the diazonium salt with copper(I) chloride and removal of the 1-substituent with hydrochloric acid, or by similar convers...
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| Format: | Journal article |
| Language: | English |
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1980
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| _version_ | 1826259342762967040 |
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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 | Ethyl 5-chloroimidazole-4-carboxylate has been prepared by diazotisation of ethyl 5-amino-1-(di-O-isopropylidene-α- or -α,β-D- mannofuranosyl)imidazole-4-carboxylate, reaction of the diazonium salt with copper(I) chloride and removal of the 1-substituent with hydrochloric acid, or by similar conversion of ethyl 5-amino-1-t-butylimidazole-4-carboxylate to ethyl 1-t-butyl-5-chloroimidazole 4-carboxylate, and removal of the t-butyl group with hydrogen bromide. Ethyl 5-fluoroimidazole-4-carboxylate has been prepared from ethyl 5-amino-1-t-butylimidazole-4-carboxylate by diazotisation and photolysis in the presence of tetrafluoroboric acid. Ethyl 5-chloroimidazole-4- carboxylate and ethyl 5-fluoroimidazole-4-carboxylate have been converted into the corresponding alcohols by reaction with lithium aluminium hydride. 5-Chloro-4-(hydroxymethyl)imidazole has also been prepared by electrolysis of 5-chloroimidazole-4-carboxylic acid at a mercury cathode. 5-Chloroimidazole has been converted into the 5-chloroimidazolyl analogues of metiamide and cimetidine by a sequence of reactions, and 5-fluoroimidazole has been similarly converted into the 5-fluoro-analogue of metiamide. The metiamide and cimetidine analogues were found to be histamine H 2-receptor antagonists. |
| first_indexed | 2024-03-06T18:48:21Z |
| format | Journal article |
| id | oxford-uuid:0f52518b-c80c-4cfc-81ed-c3fccd47b55f |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T18:48:21Z |
| publishDate | 1980 |
| record_format | dspace |
| spelling | oxford-uuid:0f52518b-c80c-4cfc-81ed-c3fccd47b55f2022-03-26T09:50:36ZPURINES, PYRIMIDINES, AND IMIDAZOLES .53. SYNTHESIS OF SOME 5-HALOGENO-ANALOGUES OF METIAMIDE AND CIMETIDINEJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:0f52518b-c80c-4cfc-81ed-c3fccd47b55fEnglishSymplectic Elements at Oxford1980Brown, TShaw, GDurant, GEthyl 5-chloroimidazole-4-carboxylate has been prepared by diazotisation of ethyl 5-amino-1-(di-O-isopropylidene-α- or -α,β-D- mannofuranosyl)imidazole-4-carboxylate, reaction of the diazonium salt with copper(I) chloride and removal of the 1-substituent with hydrochloric acid, or by similar conversion of ethyl 5-amino-1-t-butylimidazole-4-carboxylate to ethyl 1-t-butyl-5-chloroimidazole 4-carboxylate, and removal of the t-butyl group with hydrogen bromide. Ethyl 5-fluoroimidazole-4-carboxylate has been prepared from ethyl 5-amino-1-t-butylimidazole-4-carboxylate by diazotisation and photolysis in the presence of tetrafluoroboric acid. Ethyl 5-chloroimidazole-4- carboxylate and ethyl 5-fluoroimidazole-4-carboxylate have been converted into the corresponding alcohols by reaction with lithium aluminium hydride. 5-Chloro-4-(hydroxymethyl)imidazole has also been prepared by electrolysis of 5-chloroimidazole-4-carboxylic acid at a mercury cathode. 5-Chloroimidazole has been converted into the 5-chloroimidazolyl analogues of metiamide and cimetidine by a sequence of reactions, and 5-fluoroimidazole has been similarly converted into the 5-fluoro-analogue of metiamide. The metiamide and cimetidine analogues were found to be histamine H 2-receptor antagonists. |
| spellingShingle | Brown, T Shaw, G Durant, G PURINES, PYRIMIDINES, AND IMIDAZOLES .53. SYNTHESIS OF SOME 5-HALOGENO-ANALOGUES OF METIAMIDE AND CIMETIDINE |
| title | PURINES, PYRIMIDINES, AND IMIDAZOLES .53. SYNTHESIS OF SOME 5-HALOGENO-ANALOGUES OF METIAMIDE AND CIMETIDINE |
| title_full | PURINES, PYRIMIDINES, AND IMIDAZOLES .53. SYNTHESIS OF SOME 5-HALOGENO-ANALOGUES OF METIAMIDE AND CIMETIDINE |
| title_fullStr | PURINES, PYRIMIDINES, AND IMIDAZOLES .53. SYNTHESIS OF SOME 5-HALOGENO-ANALOGUES OF METIAMIDE AND CIMETIDINE |
| title_full_unstemmed | PURINES, PYRIMIDINES, AND IMIDAZOLES .53. SYNTHESIS OF SOME 5-HALOGENO-ANALOGUES OF METIAMIDE AND CIMETIDINE |
| title_short | PURINES, PYRIMIDINES, AND IMIDAZOLES .53. SYNTHESIS OF SOME 5-HALOGENO-ANALOGUES OF METIAMIDE AND CIMETIDINE |
| title_sort | purines pyrimidines and imidazoles 53 synthesis of some 5 halogeno analogues of metiamide and cimetidine |
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