Synthesis of iso-C-nucleoside analogues from 1-(methyl 2-O-benzyl-4,6-O- benzylidene-3-deoxy-α-D-altropyranosid-3-yl)but-3-yn-2-ones
dc.bibliographicCitation.firstPage | 1175 | eng |
dc.bibliographicCitation.issue | 11 | eng |
dc.bibliographicCitation.journalTitle | Zeitschrift für Naturforschung - Section B Journal of Chemical Sciences | eng |
dc.bibliographicCitation.volume | 60 | eng |
dc.contributor.author | Otero, I. | |
dc.contributor.author | Feist, H. | |
dc.contributor.author | Michalik, D. | |
dc.contributor.author | Michalik, M. | |
dc.contributor.author | Quincoces, J. | |
dc.contributor.author | Peseke, K. | |
dc.date.accessioned | 2020-08-07T13:48:30Z | |
dc.date.available | 2020-08-07T13:48:30Z | |
dc.date.issued | 2005 | |
dc.description.abstract | 1-(Methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-D-altropyranosid-3- yl)but-3-yn-2-one (3a) reacted with 3-amino-1H-1,2,4-triazole and 5-aminopyrazole-4-carboxylic acid derivatives in the presence of base to furnish the triazolo[1,5-a]pyrimidine (5) and the pyrazolo[1,5-a]pyrimidines (8a-d), respectively. Treatment of 1-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy- α-D-altropyranosid-3-yl)-4-phenyl-but-3-yn-2-one (3b) with cyanacetamide, 2-cyano-N-(4-methoxyphenyl)acetamide und N-aryl-3-oxo-butyramides afforded the substituted nicotinonitriles (11a-d). Furthermore, reaction of 3b with 2-benzimidazolyl-acetonitrile yielded the benz[4,5]imidazo[1,2-a]pyridine-4- carbonitrile (13). Deprotection of 8d in two steps afforded the 2-amino-N-benzyl-5-(methyl 3-deoxy-α-D-altropyranosid-3-yl-methyl) pyrazolo[1,5-a]pyrimidine-3-carboxamide (10). Compounds 5 and 11d were treated with AcOH/H2O to furnish the 5-(methyl 2-O-benzyl-3-deoxy-α-D- altropyranosid-3-yl-methyl)[1,2,4]triazolo[1,5-a]pyrimidine (6) and the 3-acetyl-1,2-dihydro-1-(4-methoxyphenyl)-6-(methyl 2-O-benzyl-3-deoxy-α-D- altropyranosid-3-yl-methyl)-4-phenylpyridin-2-one (12), respectively. | eng |
dc.description.version | publishedVersion | eng |
dc.identifier.uri | https://doi.org/10.34657/4022 | |
dc.identifier.uri | https://oa.tib.eu/renate/handle/123456789/5393 | |
dc.language.iso | eng | eng |
dc.publisher | Berlin : Walter de Gruyter | eng |
dc.relation.doi | https://doi.org/10.1515/znb-2005-1110 | |
dc.relation.issn | 0932-0776 | |
dc.rights.license | CC BY-NC-ND 3.0 Unported | eng |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-nd/3.0/ | eng |
dc.subject.ddc | 540 | eng |
dc.subject.other | 1,2-Dihydropyridin-2-one | eng |
dc.subject.other | Benz[4,5]imidazo[1,2-a]pyridine | eng |
dc.subject.other | C-Nucleoside Analogues | eng |
dc.subject.other | Glycosylalkynone | eng |
dc.subject.other | Pyrazolo[1,5-a]pyrimidine | eng |
dc.title | Synthesis of iso-C-nucleoside analogues from 1-(methyl 2-O-benzyl-4,6-O- benzylidene-3-deoxy-α-D-altropyranosid-3-yl)but-3-yn-2-ones | eng |
dc.type | Article | eng |
dc.type | Text | eng |
tib.accessRights | openAccess | eng |
wgl.contributor | LIKAT | eng |
wgl.subject | Chemie | eng |
wgl.type | Zeitschriftenartikel | eng |
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