• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

高效三组分一锅法合成 5-氨基-7-芳基-7,8-二氢-[1,2,4]三唑并[4,3-a]嘧啶-6-甲腈。

An efficient three component one-pot synthesis of 5-amino-7-aryl-7,8-dihydro-[1,2,4] triazolo[4,3-a]-pyrimidine-6-carbonitriles.

机构信息

College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, China.

出版信息

Molecules. 2012 Feb 14;17(2):1860-9. doi: 10.3390/molecules17021860.

DOI:10.3390/molecules17021860
PMID:22334064
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6268426/
Abstract

A series of novel 5-amino-7-aryl-7,8-dihydro-[1,2,4] triazolo[4,3-a]-pyrimidine-6-carbonitriles were synthesized by a one-pot reaction of 3-amino-1,2,4-triazole, malononitrile and aryl aldehydes in the presence of 20 mol% NaOH in ethanol under heating or ultrasonic irradiation. The structures of the target compounds were confirmed by inspection of their (1)H- NMR, (13)C-NMR, IR and MS spectra. The advantages of this method are short reaction times, good yields, high selectivity and operational simplicity.

摘要

一系列新型 5-氨基-7-芳基-7,8-二氢-[1,2,4]三唑并[4,3-a]嘧啶-6-甲腈是通过在乙醇中存在 20mol%NaOH 的条件下,将 3-氨基-1,2,4-三唑、丙二腈和芳醛一锅反应,加热或超声辐射下合成的。目标化合物的结构通过其 (1)H-NMR、(13)C-NMR、IR 和 MS 光谱进行了确认。该方法的优点是反应时间短、产率高、选择性好、操作简单。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c04a/6268426/ecf6270be577/molecules-17-01860-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c04a/6268426/ccfa19e543f1/molecules-17-01860-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c04a/6268426/ecf6270be577/molecules-17-01860-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c04a/6268426/ccfa19e543f1/molecules-17-01860-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c04a/6268426/ecf6270be577/molecules-17-01860-g002.jpg

相似文献

1
An efficient three component one-pot synthesis of 5-amino-7-aryl-7,8-dihydro-[1,2,4] triazolo[4,3-a]-pyrimidine-6-carbonitriles.高效三组分一锅法合成 5-氨基-7-芳基-7,8-二氢-[1,2,4]三唑并[4,3-a]嘧啶-6-甲腈。
Molecules. 2012 Feb 14;17(2):1860-9. doi: 10.3390/molecules17021860.
2
A facile synthesis of new 2-amino-4H-pyran-3-carbonitriles by a one-pot reaction of α, α'-bis(arylidene) cycloalkanones and malononitrile in the presence of K2CO3.在碳酸钾存在下,通过α,α'-双(亚芳基)环烷酮与丙二腈的一锅反应简便合成新型2-氨基-4H-吡喃-3-腈。
ScientificWorldJournal. 2012;2012:208796. doi: 10.1100/2012/208796. Epub 2012 Apr 1.
3
Synthesis of novel 6-phenyl-2,4-disubstituted pyrimidine-5-carbonitriles as potential antimicrobial agents.新型 6-苯基-2,4-二取代嘧啶-5-甲腈的合成及其作为潜在抗菌剂的研究。
Eur J Med Chem. 2011 Sep;46(9):4642-7. doi: 10.1016/j.ejmech.2011.08.003. Epub 2011 Aug 9.
4
Silica gel-catalyzed one-pot syntheses in water and fluorescence properties studies of 5-amino-2-aryl-3H-chromeno[4,3,2-de][1,6]naphthyridine-4-carbonitriles and 5-amino-2-aryl-3H-quinolino[4,3,2-de][1,6]naphthyridine-4-carbonitriles.硅胶催化的在水中的一锅法合成以及5-氨基-2-芳基-3H-色烯并[4,3,2-de][1,6]萘啶-4-腈和5-氨基-2-芳基-3H-喹啉并[4,3,2-de][1,6]萘啶-4-腈的荧光性质研究
J Comb Chem. 2010 Jan-Feb;12(1):31-4. doi: 10.1021/cc9001179.
5
Synthetic approaches towards benzo[h]quinoline-3-carbonitriles.苯并[h]喹啉-3-腈的合成方法。
Pharmazie. 2000 Apr;55(4):269-72.
6
A four-component reaction: regio- and chemoselective formation of 7-amino-2-(tert-butyl)-5-aryl-4,5-dihydropyrazolo[1,5-a]pyrimidine-6-carbonitrile.四组分反应:区域和化学选择性合成 7-氨基-2-(叔丁基)-5-芳基-4,5-二氢吡唑并[1,5-a]嘧啶-6-甲腈。
Mol Divers. 2020 Aug;24(3):753-761. doi: 10.1007/s11030-019-09976-x. Epub 2019 Jul 18.
7
An efficient diastereoselective synthesis of novel fused 5H-furo[2,3-d]thiazolo[3,2-a]pyrimidin-5-ones via one-pot three-component reaction.通过一锅法三组分反应高效合成新型稠合 5H-呋喃并[2,3-d]噻唑并[3,2-a]嘧啶-5-酮。
Mol Divers. 2022 Feb;26(1):183-190. doi: 10.1007/s11030-020-10173-4. Epub 2021 Jan 3.
8
A new one-pot three-component synthesis of 2,4-diamino-5H-chromeno[2,3-b]pyridine-3-carbonitrile derivatives.一种新型的 2,4-二氨基-5H-色烯并[2,3-b]吡啶-3-甲腈衍生物的一锅法三组分合成方法。
Mol Divers. 2010 Feb;14(1):179-82. doi: 10.1007/s11030-009-9152-x. Epub 2009 May 16.
9
New convenient four-component synthesis of 6-amino-2,4-dihydropyrano[2,3-c]pyrazol-5-carbonitriles and one-pot synthesis of 6'-aminospiro[(3H)-indol-3,4'-pyrano[2,3-c]pyrazol]-(1H)-2-on-5'-carbonitriles.6-氨基-2,4-二氢吡喃并[2,3-c]吡唑-5-甲腈的新型便捷四组分合成法及6'-氨基螺[(3H)-吲哚-3,4'-吡喃并[2,3-c]吡唑]-(1H)-2-酮-5'-甲腈的一锅合成法。
J Comb Chem. 2009 Sep-Oct;11(5):914-9. doi: 10.1021/cc900076j.
10
The condensation of salicylaldehydes and malononitrile revisited: synthesis of new dimeric chromene derivatives.水杨醛与丙二腈缩合反应的再探讨:新型二聚色烯衍生物的合成
J Org Chem. 2008 Mar 7;73(5):1954-62. doi: 10.1021/jo702552f. Epub 2008 Feb 14.

引用本文的文献

1
Preparation and characterization of kaolin-[TMS]-NH C(NO) as a novel heterogeneous nano-catalyst and its use in the synthesis of imidazo[1,2-]pyrimidine and 1,2,4-triazolo[4,3-]pyrimidines.高岭土-[TMS]-NH C(NO) 作为一种新型非均相纳米催化剂的制备、表征及其在咪唑并[1,2 - ]嘧啶和1,2,4 - 三唑并[4,3 - ]嘧啶合成中的应用
RSC Adv. 2025 Jul 29;15(33):26992-27015. doi: 10.1039/d5ra01292a. eCollection 2025 Jul 25.
2
New Diaryl-1,2,4-triazolo[3,4-]pyrimidine Hybrids as Selective COX-2/sEH Dual Inhibitors with Potent Analgesic/Anti-inflammatory and Cardioprotective Properties.新型二芳基-1,2,4-三唑并[3,4-b]嘧啶杂合物作为具有强效镇痛/抗炎和心脏保护特性的选择性COX-2/可溶性环氧化物水解酶双重抑制剂
ACS Omega. 2024 Jul 22;9(31):33494-33509. doi: 10.1021/acsomega.4c00870. eCollection 2024 Aug 6.
3

本文引用的文献

1
A facile and efficient ultrasound-assisted synthesis of novel dispiroheterocycles through 1,3-dipolar cycloaddition reactions.一种通过 1,3-偶极环加成反应简便高效超声辅助合成新型双螺杂环化合物的方法。
Ultrason Sonochem. 2012 Mar;19(2):264-9. doi: 10.1016/j.ultsonch.2011.07.006. Epub 2011 Jul 26.
2
Differentiation between [1,2,4]triazolo[1,5-a] pyrimidine and [1,2,4]triazolo[4,3-a]-pyrimidine regioisomers by 1H-15N HMBC experiments.通过 1H-15N HMBC 实验区分[1,2,4]三唑并[1,5-a]嘧啶和[1,2,4]三唑并[4,3-a]嘧啶区域异构体。
Magn Reson Chem. 2010 Aug;48(8):614-22. doi: 10.1002/mrc.2634.
3
Novel chromeno [2,3-b]-pyrimidine derivatives as potential anti-microbial agents.
Three Component One-Pot Synthesis and Antiproliferative Activity of New [1,2,4]Triazolo[4,3-]pyrimidines.新型[1,2,4]三唑并[4,3-a]嘧啶的三组分一锅法合成及抗增殖活性。
Molecules. 2023 May 5;28(9):3917. doi: 10.3390/molecules28093917.
4
Synthesis of pyrimidine-6-carbonitriles, pyrimidin-5-ones, and tetrahydroquinoline-3-carbonitriles by new superb oxovanadium(V)-[5,10,15,20-tetrakis(pyridinium)-porphyrinato]-tetra(tricyanomethanide) catalyst via anomeric based oxidation.新型超强氧钒(V)-[5,10,15,20-四(吡啶𬭩基)-卟啉基]-四(三氰甲烷)催化剂通过端基氧化合成嘧啶-6-腈、嘧啶-5-酮和四氢喹啉-3-腈
Sci Rep. 2022 Nov 14;12(1):19537. doi: 10.1038/s41598-022-23956-6.
5
A Novel Diamine Containing Ester and Diphenylethane Groups for Colorless Polyimide with a Low Dielectric Constant and Low Water Absorption.一种含酯基和二苯乙烷基团的新型二胺用于制备具有低介电常数和低吸水率的无色聚酰亚胺。
Polymers (Basel). 2022 Oct 25;14(21):4504. doi: 10.3390/polym14214504.
6
α-Aminoazoles/azines: key reaction partners for multicomponent reactions.α-氨基唑/嗪:多组分反应的关键反应伙伴。
RSC Adv. 2021 Mar 16;11(19):11083-11165. doi: 10.1039/d1ra00392e.
7
Sonochemical Protocols for Heterocyclic Synthesis: A Representative Review.声化学杂环合成方法:代表性综述。
Top Curr Chem (Cham). 2022 Feb 12;380(2):14. doi: 10.1007/s41061-022-00369-7.
8
Ultrasound-assisted synthesis of pyrimidines and their fused derivatives: A review.超声辅助嘧啶及其稠合衍生物的合成:综述。
Ultrason Sonochem. 2021 Nov;79:105683. doi: 10.1016/j.ultsonch.2021.105683. Epub 2021 Jul 27.
9
Agar-entrapped sulfonated DABCO: Agelly acidic catalyst for the acceleration of one-pot synthesis of 1,2,4-triazoloquinazolinone and some pyrimidine derivatives.琼脂包裹的磺化三乙烯二胺:用于加速一锅法合成1,2,4-三唑并喹唑啉酮及一些嘧啶衍生物的凝胶状酸性催化剂。
J Mol Struct. 2021 Feb 15;1226:129336. doi: 10.1016/j.molstruc.2020.129336. Epub 2020 Sep 26.
10
Transition metal-free one-pot synthesis of nitrogen-containing heterocycles.无过渡金属一锅法合成含氮杂环化合物。
Mol Divers. 2016 Feb;20(1):185-232. doi: 10.1007/s11030-015-9596-0. Epub 2015 Jun 9.
新型色烯并[2,3-b]嘧啶衍生物作为有潜力的抗菌剂。
Eur J Med Chem. 2010 Jun;45(6):2695-9. doi: 10.1016/j.ejmech.2010.02.040. Epub 2010 Feb 20.
4
A facile one-pot green synthesis and antibacterial activity of 2-amino-4H-pyrans and 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes.2-氨基-4H-吡喃和2-氨基-5-氧代-5,6,7,8-四氢-4H-色烯的简便一锅法绿色合成及其抗菌活性
Eur J Med Chem. 2009 Sep;44(9):3805-9. doi: 10.1016/j.ejmech.2009.04.017. Epub 2009 Apr 16.
5
Copper (II) complexes of [1,2,4]triazolo [1,5-a]pyrimidine derivatives as potential anti-parasitic agents.[1,2,4]三唑并[1,5-a]嘧啶衍生物的铜(II)配合物作为潜在的抗寄生虫剂
Drug Metab Lett. 2009 Jan;3(1):35-44. doi: 10.2174/187231209787176317.
6
A novel and efficient one step synthesis of 2-amino-5-cyano-6-hydroxy-4-aryl pyrimidines and their anti-bacterial activity.2-氨基-5-氰基-6-羟基-4-芳基嘧啶的新型高效一步合成及其抗菌活性
Eur J Med Chem. 2009 Jun;44(6):2651-4. doi: 10.1016/j.ejmech.2008.10.018. Epub 2008 Oct 26.
7
Essramycin: a first triazolopyrimidine antibiotic isolated from nature.埃斯拉霉素:一种从自然界中分离出的首个三唑并嘧啶类抗生素。
J Antibiot (Tokyo). 2008 Mar;61(3):149-57. doi: 10.1038/ja.2008.124.
8
Synthesis, antifungal activity and CoMFA analysis of novel 1,2,4-triazolo[1,5-a]pyrimidine derivatives.新型1,2,4-三唑并[1,5-a]嘧啶衍生物的合成、抗真菌活性及比较分子力场分析
Eur J Med Chem. 2008 Mar;43(3):595-603. doi: 10.1016/j.ejmech.2007.04.021. Epub 2007 May 27.
9
Sono-synthesis of imidazolidine-2-thione as a base compound of some pharmaceutical products.超声合成作为某些药品基础化合物的咪唑烷-2-硫酮。
Ultrason Sonochem. 2008 Feb;15(2):119-23. doi: 10.1016/j.ultsonch.2007.02.006. Epub 2007 Mar 2.
10
Power ultrasound in organic synthesis: moving cavitational chemistry from academia to innovative and large-scale applications.有机合成中的功率超声:将空化化学从学术界推向创新型大规模应用。
Chem Soc Rev. 2006 Feb;35(2):180-96. doi: 10.1039/b503848k. Epub 2005 Oct 10.