PURINES, PYRIMIDINES, AND IMIDAZOLES .51. NEW SYNTHESES OF SOME 5-ALKYL-AMINOIMIDAZOLES AND 5-DIALKYL-AMINOIMIDAZOLES - 3-ALKYLIMIDAZOLIUM NUCLEOSIDES AND 3-ALKYLPURINES
Ethyl 3-methyl-5-amino-1-(2,3-O-isopropylidene-a- and -β-D- ribofuranosyl)imidazolium-4-carboxylate iodides, the corresponding benzyl-β-D-ribofuranosyl ester, and benzyl 3-methyl-5-amino-1-(2,3,5-tri-O- acetyl-β-D-ribofuranosyl)imidazolium-4-carboxylate iodide have been prepared by methylation of th...
| Main Authors: | , , , |
|---|---|
| Format: | Journal article |
| Language: | English |
| Published: |
1979
|
| _version_ | 1826291432524087296 |
|---|---|
| author | Brown, T Kadir, K Mackenzie, G Shaw, G |
| author_facet | Brown, T Kadir, K Mackenzie, G Shaw, G |
| author_sort | Brown, T |
| collection | OXFORD |
| description | Ethyl 3-methyl-5-amino-1-(2,3-O-isopropylidene-a- and -β-D- ribofuranosyl)imidazolium-4-carboxylate iodides, the corresponding benzyl-β-D-ribofuranosyl ester, and benzyl 3-methyl-5-amino-1-(2,3,5-tri-O- acetyl-β-D-ribofuranosyl)imidazolium-4-carboxylate iodide have been prepared by methylation of the corresponding nucleosides with methyl iodide. Their reactions with acids and bases have been examined. Ethyl 4(5)-methylamino- and dimethylamino-imidazole-5(4)-carboxylates have been prepared in a sequence of reactions from ethyl cyanoacetate and the former compound was converted into 3-methylhypoxanthine by heating with formamidine acetate and into 3-methylguanine by a sequence of reactions. The methylamino-derivative undergoes a Dimroth rearrangement when heated with aqueous ammonia, to produce 1-methyl-5-aminoimidazole-carboxamide. |
| first_indexed | 2024-03-07T02:59:18Z |
| format | Journal article |
| id | oxford-uuid:b066790b-1fca-4e33-b440-2d05fb67f140 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T02:59:18Z |
| publishDate | 1979 |
| record_format | dspace |
| spelling | oxford-uuid:b066790b-1fca-4e33-b440-2d05fb67f1402022-03-27T03:56:08ZPURINES, PYRIMIDINES, AND IMIDAZOLES .51. NEW SYNTHESES OF SOME 5-ALKYL-AMINOIMIDAZOLES AND 5-DIALKYL-AMINOIMIDAZOLES - 3-ALKYLIMIDAZOLIUM NUCLEOSIDES AND 3-ALKYLPURINESJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:b066790b-1fca-4e33-b440-2d05fb67f140EnglishSymplectic Elements at Oxford1979Brown, TKadir, KMackenzie, GShaw, GEthyl 3-methyl-5-amino-1-(2,3-O-isopropylidene-a- and -β-D- ribofuranosyl)imidazolium-4-carboxylate iodides, the corresponding benzyl-β-D-ribofuranosyl ester, and benzyl 3-methyl-5-amino-1-(2,3,5-tri-O- acetyl-β-D-ribofuranosyl)imidazolium-4-carboxylate iodide have been prepared by methylation of the corresponding nucleosides with methyl iodide. Their reactions with acids and bases have been examined. Ethyl 4(5)-methylamino- and dimethylamino-imidazole-5(4)-carboxylates have been prepared in a sequence of reactions from ethyl cyanoacetate and the former compound was converted into 3-methylhypoxanthine by heating with formamidine acetate and into 3-methylguanine by a sequence of reactions. The methylamino-derivative undergoes a Dimroth rearrangement when heated with aqueous ammonia, to produce 1-methyl-5-aminoimidazole-carboxamide. |
| spellingShingle | Brown, T Kadir, K Mackenzie, G Shaw, G PURINES, PYRIMIDINES, AND IMIDAZOLES .51. NEW SYNTHESES OF SOME 5-ALKYL-AMINOIMIDAZOLES AND 5-DIALKYL-AMINOIMIDAZOLES - 3-ALKYLIMIDAZOLIUM NUCLEOSIDES AND 3-ALKYLPURINES |
| title | PURINES, PYRIMIDINES, AND IMIDAZOLES .51. NEW SYNTHESES OF SOME 5-ALKYL-AMINOIMIDAZOLES AND 5-DIALKYL-AMINOIMIDAZOLES - 3-ALKYLIMIDAZOLIUM NUCLEOSIDES AND 3-ALKYLPURINES |
| title_full | PURINES, PYRIMIDINES, AND IMIDAZOLES .51. NEW SYNTHESES OF SOME 5-ALKYL-AMINOIMIDAZOLES AND 5-DIALKYL-AMINOIMIDAZOLES - 3-ALKYLIMIDAZOLIUM NUCLEOSIDES AND 3-ALKYLPURINES |
| title_fullStr | PURINES, PYRIMIDINES, AND IMIDAZOLES .51. NEW SYNTHESES OF SOME 5-ALKYL-AMINOIMIDAZOLES AND 5-DIALKYL-AMINOIMIDAZOLES - 3-ALKYLIMIDAZOLIUM NUCLEOSIDES AND 3-ALKYLPURINES |
| title_full_unstemmed | PURINES, PYRIMIDINES, AND IMIDAZOLES .51. NEW SYNTHESES OF SOME 5-ALKYL-AMINOIMIDAZOLES AND 5-DIALKYL-AMINOIMIDAZOLES - 3-ALKYLIMIDAZOLIUM NUCLEOSIDES AND 3-ALKYLPURINES |
| title_short | PURINES, PYRIMIDINES, AND IMIDAZOLES .51. NEW SYNTHESES OF SOME 5-ALKYL-AMINOIMIDAZOLES AND 5-DIALKYL-AMINOIMIDAZOLES - 3-ALKYLIMIDAZOLIUM NUCLEOSIDES AND 3-ALKYLPURINES |
| title_sort | purines pyrimidines and imidazoles 51 new syntheses of some 5 alkyl aminoimidazoles and 5 dialkyl aminoimidazoles 3 alkylimidazolium nucleosides and 3 alkylpurines |
| work_keys_str_mv | AT brownt purinespyrimidinesandimidazoles51newsynthesesofsome5alkylaminoimidazolesand5dialkylaminoimidazoles3alkylimidazoliumnucleosidesand3alkylpurines AT kadirk purinespyrimidinesandimidazoles51newsynthesesofsome5alkylaminoimidazolesand5dialkylaminoimidazoles3alkylimidazoliumnucleosidesand3alkylpurines AT mackenzieg purinespyrimidinesandimidazoles51newsynthesesofsome5alkylaminoimidazolesand5dialkylaminoimidazoles3alkylimidazoliumnucleosidesand3alkylpurines AT shawg purinespyrimidinesandimidazoles51newsynthesesofsome5alkylaminoimidazolesand5dialkylaminoimidazoles3alkylimidazoliumnucleosidesand3alkylpurines |