含芳基四唑的糖氨基噁二唑/噻二唑衍生物的合成

郭中献; 曹玲华

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含芳基四唑的糖氨基噁二唑/噻二唑衍生物的合成

研究精粹 | 更新时间：2026-01-21

- 含芳基四唑的糖氨基噁二唑/噻二唑衍生物的合成
- 含芳基四唑的糖氨基噁二唑/噻二唑衍生物的合成
- 新疆大学学报（自然科学版中英文） 2008年110卷第2期页码：131-136
- 作者机构：
  
  新疆大学化学化工学院,新疆大学化学化工学院新疆乌鲁木齐830046,新疆,乌鲁木齐,830046
- 作者简介：
- 基金信息：
  
  国家自然科学基金20462006资助项目
- DOI：
  中图分类号： O626.2
- 纸质出版：2008
- 稿件说明：
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[1]郭中献,曹玲华.含芳基四唑的糖氨基噁二唑/噻二唑衍生物的合成[J].新疆大学学报(自然科学版),2008,No.110(02):131-136+124.

郭中献, 曹玲华. 含芳基四唑的糖氨基噁二唑/噻二唑衍生物的合成[J]. Journal of Xinjiang University (Natural Science Edition in Chinese and English), 2008, 110(2): 131-136.
[1]郭中献,曹玲华.含芳基四唑的糖氨基噁二唑/噻二唑衍生物的合成[J].新疆大学学报(自然科学版),2008,No.110(02):131-136+124. DOI：

郭中献, 曹玲华. 含芳基四唑的糖氨基噁二唑/噻二唑衍生物的合成[J]. Journal of Xinjiang University (Natural Science Edition in Chinese and English), 2008, 110(2): 131-136. DOI：

摘要

以S-(1-芳基-1H-四唑-5-基)巯乙酰肼(1a～1c)和糖基异硫氰酸酯(2a

2b)为原料

高产率地合成了新的N-糖基-2-[S-(1-芳基-1H-四唑-5-基)巯乙酰氨基]硫脲3a～3f

然后分别在醋酸汞/乙醇体系或乙酸酐/磷酸体系中合环

得到一系列新的2-(1-芳基-1H-四唑-5-硫亚甲基)-5-糖氨基噁二唑/噻二唑化合物4a～4f

5a～5f.目标化合物的结构均经IR

1HNMR及元素分析确证.

Abstract

A series of new N-glycosyl-2-[S-(1-aryl-1H-tetrazol-5-yl)mercaptoacetamido]thioureas 3a～3f have been synthesized in high yields from S-(1-aryl-1H-tetrazol-5-yl)mercaptoacetohydrazine(1a～1c) and glycosyl isothiocyanates(2a

2b)

then 3a～3f were converted to a series of new 2-(1-aryl-1H-tetrazol-5-ylthiomethylene)-5-glycosylamino-oxadiazoles/thiadiazoles 4a～4f

and 5a～5f respectively under mercuric acetate/alcohol system or acetic anhydride/phosphoric acid system.All the target compounds were characterized by IR

1H NMR and elemental analysis.

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references

Sureshbabu V V,Venkataramanarao R,Naik S A,Chennakrishnareddy G.Synthesis of tetrazole analogues of amino acids using Fmoc chemistry:isolation of amino free tetrazoles and their incorporation into peptides[J].Tetrahedron Lett.2007,48:7038-7041.

Bond A D,Fleming A,Kelleher F,et.al.Reactions of1,4-bis(tetrazole)benzenes:formation of long chain alkyl halides[J].Tetrahedron2006,62:9577-9581.

Upadhayaya R S,Jain S,Sinha N,Kishore N,et.al.Synthesis of novel substituted tetrazoles having antifungal activity[J].Eur.J.Med.Chem.2004,39:579-592.

Zabrocki J,Dunbar J B,Marshall K W,et.al.Conformational mimicry.3.Synthesis and incorporation of1,5-disubstituted tetrazole dipeptide analogs into peptides with preservation of chiral integrity:bradykinin[J].J.Org.Chem.1992,57:202-209.

Herr R J.5-Substituted-1H-tetrazoles as carboxylic acid isosteres:medicinal chemistry and synthetic methods[J].Bioorg.Med.Chem.2002,10:3379-3393.

Ahmad M,Albertshofer K,Tanaka F,et.al.Expedient synthesis of chiral1,2-and1,4-diamines:protecting group dependent regioselectivity in direct organocatalytic asymmetric Mannich reactions[J].Org.Lett.2006,8:2839-2842.

Lee K,Kim Y,Baeck K K.A quantum chemical study on the mechanism of S-coordinated tetrazole-thiolato formation by the reaction of organic isothiocyanates with metal azido complexes of Pt(II),Pd(II),and Sn[J].J.Organomet.Chem.2005,690:4319-4329.

张兴高,朱慧,张炜,等.高氮化合物在含能材料中的应用研究进展[J].含能材料.2004,12:48-53.

Shi Wei,Qian Xuhong,Song Gonghua,et.al.Syntheses and insecticidal activities of novel2-fluorophenyl-5-aryl/cyclopropyl-1,3,4-oxadiazoles[J].J.Fluor.Chem.2000,106:173-179.

Gabriel N G,Gloria M S,Zetel D F,et.al.Synthesis and antimycobacterial activity of4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines[J].Bioorg.Med.Chem.2007,15:5502-5508.

Mohamed A A,Mohammad S.Oxadiazole Mannich bases:synthesis and antimycobacterial activity[J].Bioorg.Med.Chem.Lett.2007,17:3314-3316.

Maria G M,Daniele Z,Luciano V,et.al.Antimycobacterial activity of new3-substituted5-(pyridin-4-yl)-3H-1,3,4-oxadiazol-2-one and2-thione derivatives.Preliminary molecular modeling investigations[J].Bioorg.Med.Chem.2005,13(11):3797-3809.

Zou Xianjuan,Lai Luhua,Jin Guiyu.Study on the three-dimensional quantitative structure-activity relationship of pyridazinonyl-substituted1,3,4-thiadiazoles[J].Chin.J.Chem.2005,23(8):1120-1122.

宋宝安,陈才俊,杨松金,等.2-取代硫醚-5-(3,4,5-三甲氧基苯基)-1,3,4-噻二唑类化合物的合成、结构与体外抗癌活性[J].化学学报,2005,63(18):1720-1726.

林奇,罗榕,崔文辉,等.含巯基四唑环的芳基硫脲及其衍生物的合成[J].合成化学.2006,14(1):44-46.

曹玲华,周传健,孙家宝,等.N-糖基硫代亚脲基-(硫代)磷酰胺二芳基和二烷基酯的合成[J].有机化学,2003,23(4):356-360.

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