3,5-二氨基-1H-吡唑-4-甲腈 | 6844-58-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 亚胺内酰胺
• 中文名称: 3,5-二氨基-1H-吡唑-4-甲腈
• 英文名称: 3,5-diamino-1H-pyrazole-4-carbonitrile
• 英文别名: 3,5-diamino-4-cyano-1H-pyrazole；3,5-Diamino-4-cyan-pyrazol
• CAS: 6844-58-2
• 化学式: C₄H₅N₅
• 分子量: 123.117
• InChiKey: UKASYLSHAZSEEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P261,P280,P301+P310,P311
• 危险品运输编号：
  2811
• 危险性描述：
  H301+H311+H331

反应信息

• 作为反应物：
  描述：

  3,5-二氨基-1H-吡唑-4-甲腈 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 3,5-二氨基-1-甲基吡唑-4-甲腈
  参考文献：
  名称：

  Substituted pyrazolopyrimidine compounds

  摘要：

  提供了一种新的除草剂，即公式为：##STR1## 的取代的吡唑嘧啶类化合物，其中A代表-CO-NR.sup.6-或-C(OR.sup.7).dbd.N-，R.sup.1、R.sup.2、R.sup.3、R.sup.4、R.sup.6和R.sup.7是规范中定义的取代基团，以及它们的盐和酸加成盐。还提供了其制备方法，以及包含它们的除草剂组合物和使用它们进行除草的方法。

  公开号：

  US04163846A1
• 作为产物：
  描述：

  2-氨基乙氧基亚甲基丙二腈 在 一水合肼 作用下， 生成 3,5-二氨基-1H-吡唑-4-甲腈
  参考文献：
  名称：

  Cyanocarbon Chemistry. VIII.¹ Heterocyclic Compounds from Tetracyanoethylene

  摘要：

  DOI：

  10.1021/ja01544a058

文献信息

• Synthesis of new substituted pyrazolo[1,5-a]-pyrimidines and pyrazolo[1,5-a]1,3,5-triazines
  作者：W. Ried、S. Aboul-Fetouh

  DOI：10.1016/s0040-4020(01)86083-x

  日期：1988.1

  react with appropriate biselectrophilic reagents in the presence of (TEA) to give the substitution products pyrazolo[1,5-a]pyrimidines 4a-d, 6a-d and pyrazolo[1,5-a ]1,3,5-triazines 8a-d. Compounds 6a and 8a react with secondary amines to 10a-c and 11a-c. Treatment of 2a with malonodinitrile results in the substituted pyrazolo-[1,5-a]pyrimidine 16. Condensation of 2a, 2c and 2d with ethyli-dene-malodintriles

  5-取代的3-氨基-1H-吡唑-4-腈2a-d在（TEA）存在下与适当的双亲电子试剂反应，得到取代产物吡唑并[1,5-a]嘧啶4a-d，6a-d和吡唑并[1,5-a] 1,3,5-三嗪8a-d。化合物6a和8a与仲胺反应生成10a-c和11a-c。用丙二腈处理2a导致取代的吡唑并-[1，5-a]嘧啶16。2a，2c和2d的凝结与乙基-二烯-丙二腈一起生成外消旋的二氢-吡唑并[1,5-a]吡啶亚胺18a-e。二烯20与异二烯键体21的反应导致形成Diels-Alder加合物22。
• Anellation and Ring Transformations of Push-pull-functionalized Deoxypyranosiduloses
  作者：Marcus Kordian、Holger Feist、Klaus Peseke

  DOI：10.1515/znb-2009-0613

  日期：2009.6.1

  d-2-ulose 5 with substituted 5- aminopyrazoles afforded the pyrano-anellated pyrazolo[1,5-a]pyrimidines 8. The treatment of the corresponding (E)-2-aminomethylene-α-D-erythro-hexopyranosid-3-ulose 6 with 5-aminopyrazoles and (benzimidazol-2-yl)acetonitrile yielded in a ring transformation process the D-erythronoyl-pyrazolo[ 1,5-a]pyrimidine-3-carbonic acid derivatives 10 and D-erythronoyl-pyrido[1

  (E)-3-氨基亚甲基-α-D-erythro-hexopyranosid-2-ulose 5 与取代的 5-aminopyrazoles 反应得到吡喃烷化的吡唑并 [1,5-a] 嘧啶 8. 相应的 (E) 的处理)-2-氨基亚甲基-α-D-erythro-hexopyranosid-3-ulose 6 与 5-aminopyrazoles 和 (benzimidazol-2-yl) 乙腈在环转化过程中产生 D-erythronoyl-pyrazolo[1,5-a] pyrimidine-3-carbonic acid 衍生物 10 和 D-erythronoyl-pyrido[1,2-a]benzimidazole-4-carbonitrile (12)，分别是推拉功能化的脱氧吡喃糖苷糖的图形摘要编环和环转化
• NN bridged pyrazoles from nitrogen‐centered radicals: A comparative study of spin densities, molecular structures, and reactivities
  作者：Zhiwei Zeng、Wei Huang、Yuji Liu、Yongxing Tang

  DOI：10.1002/jhet.4745

  日期：2024.1

  undergo diverse reactions. However, the utility of these reactive species in NN coupling reactions, especially in nitrogen-rich heterocycles, remains a significant challenge due to the high electronegativity of the nitrogen atoms and the poor molecular stability of high-nitrogen compounds. In this work, the possibility of NH bond cleavage in different functionalized pyrazoles to produce corresponding

  以氮为中心的自由基是多功能的合成中间体，能够进行多种反应。然而，由于氮原子的高电负性和高氮化合物的分子稳定性差，这些活性物质在N - N偶联反应中的应用，特别是在富氮杂环中，仍然是一个重大挑战。本工作通过密度泛函理论计算研究了不同官能化吡唑中N - H键断裂产生相应氮中心自由基的可能性。根据计算结果，合成了具有预期反应效率的N - N桥接4c和4e ，并通过前沿分子轨道理论对其进行了进一步分析。此外，还研究了合成的N - N桥联吡唑的分子稳定性。
• The Discovery of in Vivo Active Mitochondrial Branched-Chain Aminotransferase (BCATm) Inhibitors by Hybridizing Fragment and HTS Hits
  作者：Sophie M. Bertrand、Nicolas Ancellin、Benjamin Beaufils、Ryan P. Bingham、Jennifer A. Borthwick、Anne-Bénédicte Boullay、Eric Boursier、Paul S. Carter、Chun-wa Chung、Ian Churcher、Nerina Dodic、Marie-Hélène Fouchet、Charlène Fournier、Peter L. Francis、Laura A. Gummer、Kenny Herry、Andrew Hobbs、Clare I. Hobbs、Paul Homes、Craig Jamieson、Edwige Nicodeme、Stephen D. Pickett、Iain H. Reid、Graham L. Simpson、Lisa A. Sloan、Sarah E. Smith、Donald O’N. Somers、Claus Spitzfaden、Colin J. Suckling、Klara Valko、Yoshiaki Washio、Robert J. Young

  DOI：10.1021/acs.jmedchem.5b00313

  日期：2015.9.24

  The hybridization of hits, identified by complementary fragment and high throughput screens, enabled the discovery of the first series of potent inhibitors of mitochondrial branched-chain aminotransferase (BCATm) based on a 2-benzylamino-pyrazolo[1,5-a]-pyrimidinone-3-carbonitrile template. Structure-guided growth enabled rapid optimization of potency with maintenance of ligand efficiency, while the focus on physicochemical properties delivered compounds with excellent pharmacokinetic exposure that enabled a proof of concept experiment in mice. Oral administration of 2-((4-chloro-2,6-difluorobenzyl)amino)-7-oxo-5-propyl-4,7-dihydropyrazolo[1,5-a]-pyrimidine-3-carbonitrile 61 significantly raised the circulating levels of the branched-chain amino acids leucine, isoleucine, and valine in this acute study.
• The conversion of isothiazoles into pyrazoles using hydrazine
  作者：Heraklidia A. Ioannidou、Panayiotis A. Koutentis

  DOI：10.1016/j.tet.2009.06.041

  日期：2009.8

  The conversion of isothiazoles into pyrazoles on treatment with hydrazine is investigated. The influence of various C-3, C-4 and C-5 isothiazole substituents and some limitations of this ring transformation are examined. When the isothiazole C-3 substituent is a good nucleofuge, 3-aminopyrazoles are obtained. However, when the 3-substituent is not a leaving group it is retained in the pyrazole product. Treatment of 4-bromo-3-chloro-5-phenylisothiazoie 56 or 3-chloro-4,5-diphenylisothiazole 57 with anhydrous hydrazine at ca. 200 degrees C for a few minutes gives the corresponding 3-hydrazinoisothiazoles 61 and 64 respectively in high yields; the stability of these new hydrazines is investigated. 5,5'-Diphenyl-3,3'-biisothiazole-4,4'-dicarbonitrile 78 reacts with hydrazine to give 5,5'-diphenyl-3,3'-bi(1H-pyi-azole)-4,4'-dicarbonitrile 79. Methylhydrazine reacts with 3-chloro-5-phenytisothiazole-4-carbonitrile 1 to give 3-(1-methylhydrazino)-5-phenylisothiazole-4-carbontrile 83 and 3-amino-lmethyl-5-phenylpyrazole-4-carbonitrile 84. All products are fully characterised and rational mechanisms for the isothiazole into pyrazole transformation are proposed. (C) 2009 Elsevier Ltd. All rights reserved.