Synthesis of 'reversed' pyrimidine and pyrazolo [1,5-a]pyrimidine-C-nucleoside analogues from push-pull functionalized α-D-xylo-hept-5-ulofuranurononitrile

被引：1

作者：

Hashmi, Imran Ali ^{[1
]}

Ali, Firdous Lmran

Feist, Holger

Michalik, Manfred

Reinke, Helmut

Peseke, Klaus

机构：

[1] Univ Karachi, Dept Chem, Karachi 75270, Pakistan

[2] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[3] Leibniz Inst Organ Katalyse, D-18059 Rostock, Germany

来源：

SYNTHESIS-STUTTGART | 2007年 / 18卷 / 18期

关键词：

enzyme inhibitors; C-nucleosides; monosaccharide derivatives; cyclization; pyrazoles;

D O I：

10.1055/s-2007-983879

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-O-Benzyl-6-deoxy-1,2-O-isopropylidene-6-[bis(methylsulfanyl)methylene]-alpha-D-xylo-hept-5-ulofuranurononitrile (1) was reacted with acetamidinium chloride, S-methylisothiouronium sulfate, and guanidinium chloride, respectively, in the presence of triethylamine to furnish the 2-substituted 4-(3-O-benzyl-1,2-O-isopropylidene-alpha-D-xylo-tetrofuranos-4-yl)-6-methylsulfanylpyrimidine-5-carbonitriles 2a-c. Treatment of I with different 5-aminopyrazole-4-carboxylic acid derivatives yielded the 8-(3-O-benzyl-1,2-O-isopropylidene-alpha-D-xylo-tetrofuranos-4-yl)-6-methylsulfanylpyrazolo[1,5-a]pyrimidine-3,7-dicarboxylic acid derivatives 3a-c.

引用

页码：2819 / 2822

页数：4

共 25 条

[21] 2-tert-butyl-5-methyl-7,8-dihydro-6H-cyclopenta[e]pyrazolo[1,5-a]pyrimidine:: molecular stacks built from C-H•••π(pyrazole) hydrogen bonds and π-π stacking interactions
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ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2008, 64 : O471 - O473
[22] A novel synthesis of pyridine-2(1H)-thione, pyrazolo[3,4-b]pyridine, pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine, thieno[2,3-b]pyrdine, and pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine derivatives containing a naphthyl moiety
Fattah, Azza M. Abdel
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PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2007, 182 (06) : 1351 - 1364
[23] 7-Amino-5-methyl-2-phenyl-6-(phenyldiazenyl)pyrazolo[1,5-a]pyrimidine crystallizes with Z′=2: pseudosymmetry and the formation of complex sheets built from N-H•••N and C-H•••π(arene) hydrogen bonds
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ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2010, 66 : O133 - O136
[24] Facile synthesis and characterization of novel pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidin-4(3H)-one and pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine incorporating 1,3-diarylpyrazole moiety
Sanad, Sherif M. H.
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SYNTHETIC COMMUNICATIONS, 2018, 48 (14) : 1847 - 1856
[25] Facile synthesis and characterization of novel pyrido[3,2:4,5]thieno[3,2-d]pyrimidin-4(3H)-one and pyrido[2,3:3,4]pyrazolo[1,5-a]pyrimidine incorporating 1,3-diarylpyrazole moiety (vol 48, pg 10617, 2019)
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Hawass, Mahmoud A. E.
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SYNTHETIC COMMUNICATIONS, 2019, 49 (10) : 1344 - 1344

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