6-azido-1,3-diphenyluracil | 135396-39-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-azido-1,3-diphenyluracil
• 英文别名: 6-azido-1,3-diphenylpyrimidine-2,4-dione
• CAS: 135396-39-3
• 化学式: C₁₆H₁₁N₅O₂
• 分子量: 305.296
• InChiKey: NRKBNUPCFKRPMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-azido-1,3-diphenyluracil 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二苯醚 为溶剂， 反应 2.0h， 生成 1,3-Diphenyl-6,8,9,10-tetrahydro-1H,7H-pyrimido[4,5-b]quinoline-2,4,5-trione
  参考文献：
  名称：

  Pyrido[2,3-d]pyrimidines, II. One step synthesis of pyrido[2,3-d]pyrimidines and pyrimido[4,5-b]quinolines from 6-amino uracils

  摘要：

  Reduction of 6-azidouracils 2 with hydrogen palladium or sodium dithionite afforded the corresponding 6-aminouracils 5 which could also be obtained by reaction of 2 with triphenylphosphane via phosphazenes and subsequent hydrolysis (Staudinger reaction). The use of trimethylphosphite instead of phosphanes yields with 2b the expected trimethoxyphosphazene 3c, whereas 2a reacts to the phosphonoaminopyrimidine 4. The syntheses of 5-hydroxy pyrido[2,3-d]pryimidine-2,4,7-triones 6, pyrido [2,3-d]pyrimidine-2,4,5-triones 8, cyclopenta[e]pyrido[2,3-d]pyrimidin-2,4,5-triones 7a, c, and tetrahydro-pyrimido[4,5-b]quinolin-2,4,5-triones 7b,d by condensation of 6-aminouracils 5 with malonates, ethylaceto/benzoylacetate, ethyl 2-oxocyclopentanecarboxylate and ethyl 2-oxocyclohexanecarboxylate, respectively, are described.

  DOI：

  10.1007/bf00807031
• 作为产物：
  描述：

  双苯基脲 在 sodium azide 、 三氯氧磷 作用下， 以 水 、 乙酸酐 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.83h， 生成 6-azido-1,3-diphenyluracil
  参考文献：
  名称：

  嘧啶啶氮氧化物有机光氧化还原催化剂：固态的表征，应用和非共价相互作用

  摘要：

  在这里，我们报告基于嘧啶基吡啶N-氧化物的杂环的光和电化学表征。肉桂酸衍生物的光介逆热力学E → Z异构化以及使用分子氧作为温和氧化剂将2-苯基苯甲酸氧化成环苯并香豆素，展示了它们作为有机光氧化还原催化剂的潜力。此外，根据晶体学和理论数据，讨论了固态中前所未有的分子间非共价n -π-空穴相互作用。

  DOI：

  10.1002/chem.201900118

文献信息

• Design and the synthesis of <scp>1‐heteroaryl</scp> ‐1,2,3‐triazoles connected to coumarins via ether linker
  作者：Muthipeedika Nibin Joy、Nikolai Beliaev、Tetyana V. Beryozkina、Vasiliy A. Bakulev

  DOI：10.1002/jhet.4025

  日期：2020.8

  In this paper, we report an efficient and versatile methodology for the synthesis of a series of novel heteroaryl‐1,2,3‐triazoles connected to 4‐methylcoumarin (4‐methyl‐2H‐chromen‐2‐one) via oxymethylene linker. The desired molecules were accessed by both two‐step synthesis and the one‐pot copper catalyzed cycloaddition reaction of heteroaromatic azides with coumarin containing acetylenes. The developed

  在本文中，我们报告了一种高效且通用的方法，用于合成一系列通过甲醛连接基连接到4-甲基香豆素（4-甲基-2H-铬-2--2-酮）的杂芳基-1,2,3-三唑。通过两步合成以及杂芳族叠氮化物与含有乙炔的香豆素的一锅铜催化的环加成反应，均可获得所需的分子。已发现开发的方案既容易又有效，可以以高收率制备一系列新型杂芳基-1,2,3-三唑-香豆素共轭物。成功地通过克级合成1,3-二甲基-6-（4-[（[[4-甲基-2-氧代-2H-铬--7-基]氧基]一锅法证实了一锅法的实用性甲基] -1H-1,1,2,3-三唑-1-基）嘧啶-2,4（1H，3H）-二酮。
• Ring closure reactions of azidouracils to oxazolo- and isoxazolopyrimidines
  作者：Dang Van Tinh、Wolfgang Stadlbauer

  DOI：10.1002/jhet.5570330404

  日期：1996.7

  presence of polyphosphoric acid leads either to oxazolo[5,4-d]pyrimidine-5,7-diones 5 (by reaction with benzoic acid 2a) or to isoxazolo[3,4-d]pyrimidine-4,6-diones 7 (by reaction with aliphatic carboxylic acids 2b,c). 5-Benzoylpyrimidinetriones 12 could be shown to cyclize to isoxazolo[5,4-d]pyrimidine-4,6-diones 15 by chlorination with phosphorus pentachloride and subsequent reaction with sodium azide.

  在多磷酸存在下对6-azidouracils 1的热解会生成恶唑并[5,4- d ]嘧啶-5,7-二酮5（通过与苯甲酸2a反应）或异恶唑并[3,4- d ]嘧啶-4，6-二酮7（通过与脂族羧酸2b，c反应）。通过用五氯化磷氯化并随后与叠氮化钠反应，可以显示5-苯甲酰基嘧啶三酮12环化成异恶唑并[5,4 - d ]嘧啶-4,6-二酮15。
• A facile access for the synthesis of 1-hetero(aryl)-1,2,3-triazoles linked to equol under mild conditions
  作者：Muthipeedika Nibin Joy、Nikolai Beliaev、Tetyana V. Beryozkina、Vasiliy A. Bakulev

  DOI：10.1080/00397911.2020.1792932

  日期：2020.10.17

  Abstract We herein report a convenient methodology for the synthesis of 1-hetero(aryl)-1,2,3-triazoles linked with equol by utilizing copper-catalyzed azide-alkyne cycloaddition reaction under exceptionally mild conditions. The salient features of this developed protocol include: easy isolation process, good to excellent yield of the products and appendage diversity of heteroaryl triazoles. Graphical

  摘要 我们在此报告了一种在极其温和的条件下利用铜催化的叠氮化物-炔环加成反应合成与雌马酚相连的 1-杂（芳基）-1,2,3-三唑的简便方法。该开发协议的显着特点包括：易于分离过程、产品的良好收率和杂芳基三唑的附属物多样性。图形概要
• A catalyst-free one-step synthesis of N-pyrimidinyl amidines from endocyclic enamines and 4-azidopyrimidines
  作者：Nikolai A. Beliaev、Tetyana V. Beryozkina、Gert Lubec、Vasiliy A. Bakulev

  DOI：10.1016/j.mencom.2019.01.015

  日期：2019.1

  Novel N-pyrimidyl amidines of alycyclic acids were obtained in one step from of 4-azidopyrimidines and endocyclic enamines. The reaction mechanism involves [3 + 2]-addition of azide at the double bond followed by cleavage of thus formed 1,2,3-triazoline ring, and a contraction of alicycle.

  一步法从4-叠氮基嘧啶和内环烯胺中获得了新的N-嘧啶基N基。反应机理包括在双键上叠氮化物的[3 + 2]加成，然后裂解如此形成的1,2,3-三唑啉环，并脂环族收缩。
• Mechanistic aspects of the oxidation of 1,3-disubstituted 6-amino-5-nitrosouracils with lead tetraacetate: the formation of pyrimido[5,4-g]pteridinetetrone 10-oxides
  作者：Magoichi Sako、Seiji Ohara、Kosaku Hirota、Keuji Kano、Yoshifumi Maki、Edward C. Taylor

  DOI：10.1021/jo00022a017

  日期：1991.10

  Lead tetraacetate oxidation of 1,3-disubstituted 6-amino-5-nitrosouracils 1 in glacial acetic acid results in the formation of 1,3,6,8-tetrasubstituted pyrimido[5,4-g]pteridine-2,4,5,7(1H,3H,6H,8H)-tetrone 10-oxides 2. ESR studies and a number of chemical observations suggest a novel reaction sequence involving oxidative dimerization of 1 followed by intramolecular cyclization, oxidation, and homolytic elimination of nitrous oxide.