4,5-dihydro-5-oxo-[1,2,4]triazolo[1,5-a]pyrimidine | 14384-66-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: 4,5-dihydro-5-oxo-[1,2,4]triazolo[1,5-a]pyrimidine
• 英文别名: [1,2,4]triazolo[1,5-a]pyrimidin-5(4H)-one；4H-symm.-Triazolo<1,5-a>pyrimidon-(5)；5-Oxo-4,5-dihydro-s-triazolo <1,5-a> pyrimidin；6-Oxo-1,2,4-triazolo<2,3-a>pyrimidin；4H-[1,2,4]triazolo[1,5-a]pyrimidin-5-one；4H-[1,2,4]Triazolo[1,5-a]pyrimidin-5-on；4,5-dihydro-1,2,4-triazolo[1,5-a]pyrimidin-5-one；4H,5H-[1,2,4]triazolo[1,5-a]pyrimidin-5-one；4H-[1,2,4]triazolo[1,5-a]pyrimidin-5-one
• CAS: 14384-66-8
• 化学式: C₅H₄N₄O
• mdl: MFCD12913174
• 分子量: 136.113
• InChiKey: RDHMBEKEDDDWOF-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-dihydro-5-oxo-[1,2,4]triazolo[1,5-a]pyrimidine 、 三甲基氢氧化锡 以 甲醇 为溶剂， 生成 [Me3Sn(4,5-dihydro-5-oxo-[1,2,4]triazolo-[1,5a]pyrimidine(-1H))]
  参考文献：
  名称：

  Synthesis, characterization, and in vitro antimicrobial activity of organotin(IV) complexes with triazolo-pyrimidine ligands containing exocyclic oxygen atoms

  摘要：

  Tri-organotin(IV) complexes of the triazolo-pyrimidine derivatives 4,5-dihydro-5-oxo-[1,2,4]triazolo-[1,5a]pyrimidine (5HtpO), 4,7-dihydro-5-methyl-7-oxo-(1,2,4]triazolo-[1,5a]pyrimidine (HmtpO), and 4,5,6,7-tetrahydro-5,7-dioxo-(1,2,4]triazolo-[1,5a]pyrimidine (H(2)tpO(2)), and the diorganotin derivative n-Bu2Sn(tpO(2)), were synthesized and characterized by means of infrared and Sn-119 Mossbauer spectroscopy. In all the complexes obtained the triazolopyrimidines act as multidentate ligands producing polyrneric structures.A trigonal bipyramidal arrangement of the ligands around the tin atom is proposed for triorganotin(IV) derivatives, with organic groups on the equatorial plane and bridging anionic ligands.DFT calculations were performed on the structure of H(2)tpO(2) and on its rnono- an di-anions, to investigate their harmonic vibrational modes. The observed trend of the experimental and calculated carbonyl stretching frequencies furnishes a support for the interpretation of the structure of the organotin(IV) complexes obtained with this ligand.The structure of n-Bu2Sn(tpO(2)) was elucidated by quantum chemical calculations, performed on a model system of the polyrneric complex by a two layers ONIOM method. The combined experimental and theoretical results obtained support for a trans-n-Bu-2 distorted octahedral geometry, with the tPO(2)(2-) units acting as bis-chelate ligands bridging the diorganotin(IV) moieties, and with the N(1)O(7) and N(4)O(5) chelating groups in the equatorial plane showing a cis-O-2, or cis-N-2, coordination.In vitro antimicrobial tests were performed on n-Bu3Sn(HtpO(2)) and Ph3Sn(HtpO(2)), and a good antifungal and antibiofilm activity was observed, in particular for n-Bu3Sn(HtpO(2)). (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.07.072
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 生成 4,5-dihydro-5-oxo-[1,2,4]triazolo[1,5-a]pyrimidine
  参考文献：
  名称：

  5-hydroxy-1, 3, 4-triazaindolizines as stabiliziers for photographic silver-halide emulsions

  摘要：

  公开号：

  US02450397A1

文献信息

• Structurally Different Dinuclear Copper(II) Complexes with the Same Triazolopyrimidine Bridging Ligand
  作者：Mohammad Abul Haj、Miguel Quirós、Juan M. Salas、José A. Dobado、José Molina Molina、Manuel G. Basallote、M. Ángeles Máñez

  DOI：10.1002/1099-0682(200203)2002:4<811::aid-ejic811>3.0.co;2-9

  日期：2002.3

  binuclear copper(II) compounds with the anionic form of the ligand 4,5-dihydro-5-oxo[1,2,4]triazolo[1,5-a]pyrimidine (5tpO - ) have been isolated, their formulae being [Cu2(5tpO)4(H2O)2]·2H2 O( 1), [Cu2(phen)2(5tpO)2(H2O)2](NO3)2·4H2 O( 2), [Cu2(biim)2(5tpO)2(H2O)](ClO4)2·5.5H2O (3), and [Cu2(CH3CO2)2(5tpO)2(H2O)2 ]( 4) (phen = 1,10phenanthroline, biim = bisimidazole). A related mononuclear complex, [Cu

  已分离出四种具有阴离子形式的配体 4,5-dihydro-5-oxo[1,2,4]triazolo[1,5-a]pyrimidine (5tpO - ) 的双核铜 (II) 化合物，它们的分子式为[Cu2(5tpO)4(H2O)2]·2H2 O( 1), [Cu2(phen)2(5tpO)2( )2](NO3)2·4H2 O(2), [Cu2(biim)2 (5tpO)2( )](ClO4)2·5.5 (3) 和 [Cu2(CH3CO2)2(5tpO)2( )2 ](4)（phen = 1,10 菲咯啉，biim = 双咪唑）。还制备了相关的单核络合物 [Cu(phen)2(5HtpO)2]( )2 (5)。化合物 1-3 的晶体结构已通过 X 射线衍射确定，显示它们具有四 (1) 或两个 (2, 3) 桥接 5tpO- 部分的双核性质。三唑并嘧啶配体通过化合物 1 和
• Synthetic Versatility of β-Alkoxyvinyl Trichloromethyl Ketones for Obtaining [1,2,4]Triazolo[1,5-a]pyrimidines
  作者：Nilo Zanatta、Laura Souza、Josiane Santos、Mateus Mittersteiner、Valquiria Andrade、Marcio Lobo、Felipe Santos、Adailton Bortoluzzi、Helio Bonacorso、Marcos Martins

  DOI：10.1055/s-0037-1610191

  日期：2018.9

  synthesis of [1,2,4]triazolo[1,5-a]pyrimidines, in which the trichloromethyl group is either maintained or eliminated from the product by simply controlling the reaction medium, is reported. These enones react with 3-amino-1H-1,2,4-triazoles under acidic conditions to furnish exclusively 7-(trichloromethyl)-[1,2,4]triazolo[1,5-a]pyrimidines, whereas under basic conditions [1,2,4]triazolo[1,5-a]pyrimidin-5/7(1H)-ones

  摘要 4-烷氧基-4-烷基/芳基-1,1,1-三氯烷基-3-en-2-ones（烯酮）的合成多功能性，可合成[1,2,4]三唑[1,5- a ]据报道，通过简单地控制反应介质，可以保持或从产物中除去三氯甲基的嘧啶。这些烯酮在酸性条件下与3-氨基-1 H -1,2,4-三唑反应，仅提供7-（三氯甲基）-[1,2,4]三唑[1,5- a ]嘧啶，而在碱性条件下条件[1,2,4] triazolo [1,5- a ]嘧啶-5/7 （1 H在消除三氯甲基的情况下获得-。在碱性条件下进行的反应的区域选择性受到起始烯酮中存在的取代基的高度影响。使用这两种方法合成了21个示例，收率高达86％。 4-烷氧基-4-烷基/芳基-1,1,1-三氯烷基-3-en-2-ones（烯酮）的合成多功能性，可合成[1,2,4]三唑[1,5- a ]据报道，通过简单地控制反应介质，可以保持或从产物中除去三氯甲基的嘧啶。这些烯酮在酸性条件下与3-氨基-1
• Dinuclear Pd(II) complexes with the anionic form of 4,5-dihydro-1,2,4-triazolo[1,5-a]pyrimidine-5-one
  作者：Mohammad Abul-Haj、Miguel Quirós、Juan M. Salas

  DOI：10.1016/j.poly.2004.07.024

  日期：2004.9

  This article describes the synthesis, spectroscopic characterization and single crystal X-ray structure of several Pd(II) dinuclear complexes with the ligand 4,5-dihydro-1,2,4-triazolo[1,5-a]pyrimidine-5-one (5HtpO) in its anionic form (5tpO(-)). The synthesis and characterization of the related mononuclear compound [PdCl2(5HtPO)(2)] is also included. This compound is transformed into the dinuclear [Pd-2(5tPO)(4)] (.) 4H(2)O by raising the pH, the structure of which indicates a head-tail-head-tail disposition of the heterocycles (D-2d symmetry) as a difference with the analogous Cu(II) and Pt(II) clusters. Using the auxiliary ligands bipyridine (bpy), phenanthroline (phen) and traiis-1,2-diaminocyclohexane (t-dach, racemic mixture), dinuclear compounds with the general formula [Pd-2(5tPO)2(a-a)(2)](NO3)(2) (.) nH(2)O are obtained. The crystal structure of those with a-a = phen and a-a = t-dach have been solved showing a head-tail disposition of the organic ligands, in contrast with the NMR data for a-a = bpy, which point to a head-head disposition. (C) 2004 Elsevier Ltd. All rights reserved.
• 5-Oxo and 7-oxo derivatives of [1,2,4]triazolo-[1,5-a]pyrimidine: characterization and theoretical study
  作者：M. Abul Haj、J.M. Salas、M. Quirós、J. Molina、R. Faure

  DOI：10.1016/s0022-2860(99)00303-8

  日期：2000.2

  4,5-Dihydro-5-oxo-[ 1,2,4]triazolo-[1,5-a]pyrimidine (5HtpO) and 4,7-dihydro-7-oxo-[1,2,4]triazolo-[1,5-a]pyrimidine (7HtpO) have been synthesized by the condensation of 3-amino-[1,2,4]triazole with a reagent bearing the three carbon atoms that close the six-membered ring in a strongly acidic (7HtpO) or strongly basic (5HtpO) medium. The crystal structures of these compounds have been determined by X-ray diffraction, exhibiting the N4-H tautomer, as expected from the RHF/AM1 calculations. The different possibilities for binding metal ions are discussed from the MO results. (C) 2000 Elsevier Science B.V. All rights reserved.
• Diaquabis(4,5-dihydro-1,2,4-triazolo[1,5-<i>a</i>]pyrimidin-5-one-<i>N</i>³)bis(thiocyanato-<i>N</i>)nickel(II)
  作者：Mohammad Abul-Haj、Miguel Quirós、Juan M. Salas

  DOI：10.1107/s0108270100007198

  日期：2000.8.15

  The title compound, [Ni(NCS)(2)(C5H4N4O)(2)(H2O)(2)], crystallizes in the triclinic space group P (1) over bar. The molecular unit contains two neutral molecules of 4,5-dihydro-1,2,4-triazolo[1,5-a]pyrimidin-5-one (5HtpO) coordinated through the N atom in position 3, two thiocyanate ligands coordinated through their N atoms and two water molecules completing an octahedral environment around the Ni-II ion, which lies on a centre of inversion. The structure is stabilized by hydrogen bonding. Distances in the coordination sphere are Ni- N3(5HtpO) 2.132 (2), Ni-O(water) 2.085 (2) and Ni- N(thiocyanato) 2.040 (2) Angstrom.