3-(2-furyl)-3-oxo-2-(phenylhydrazono)propanal | 337512-13-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2-furyl)-3-oxo-2-(phenylhydrazono)propanal
• 英文别名: 3-(2-furyl)-3-oxo-2-phenylhydrazonopropanal；(2E)-3-(furan-2-yl)-3-oxo-2-(phenylhydrazinylidene)propanal
• CAS: 337512-13-7
• 化学式: C₁₃H₁₀N₂O₃
• 分子量: 242.234
• InChiKey: DFAHAWHPFTWAGJ-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.67
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(2-furyl)-3-oxo-2-(phenylhydrazono)propanal 在 sodium ethanolate 、 二乙胺 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 6-(Furan-2-carbonyl)-2-phenylpyridazin-3-one
  参考文献：
  名称：

  NEW SYNTHESES OF SUBSTITUTED PYRIDAZIN-6-ONES AND PYRIDAZIN-6-IMINES

  摘要：

  DOI：

  10.1080/00304949909355339
• 作为产物：
  描述：

  3-(furan-2-yl)-2-imino-3-oxopropanal 、 苯胺 在 盐酸 、 sodium nitrite 、 sodium hydroxide 作用下， 以 水 、 乙醇 为溶剂， 反应 1.0h， 生成 3-(2-furyl)-3-oxo-2-(phenylhydrazono)propanal
  参考文献：
  名称：

  Arylhydrazonals as the aldehyde component in Baylis–Hillman reactions

  摘要：

  Arylhydrazonals were added to acrylonitrile or methyl vinyl ketone in the presence of DABCO or benzotriazole to yield the intermediate Baylis-Hillman adduct that cyclized under the reaction conditions with water elimination to yield dihydropyridazines. A pyridazine reacted with DMAD to yield a pyridine via a [4+2] Diels-Alder addition followed by retro Diels-Alder elimination of methylene aniline. Two pyridazines were condensed with DMFDMA to yield the corresponding enaminones that reacted with NH2NH2 to afford the pyrazolylpyridazines. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2008.06.026

文献信息

• Efficient synthesis of 3-aroylcinnolines from aryl methyl ketones
  作者：Nouria A Al-Awadi、Mohamed Hilmy Elnagdi、Yehia A Ibrahim、Kamini Kaul、Ajith Kumar

  DOI：10.1016/s0040-4020(00)01141-8

  日期：2001.2

  An efficient synthesis of 3-aroylcinnolines starting from the appropriate aryl methyl ketones is described. The latter were converted in two steps to the corresponding 3-oxo-3-aryl-2-arylhydrazonopropanals, which upon acid catalyzed cyclization in conc. sulfuric acid or polyphosphoric acid (PPA) led to the corresponding 3-aroylcinnolines.

  描述了从合适的芳基甲基酮开始的3-芳基肉桂啉的有效合成。将后者分两步转化为相应的3-氧代-3-芳基-2-芳基肼基丙醛，其在浓盐酸中经酸催化环化。硫酸或多磷酸（PPA）生成相应的3-aroylcinnolines。
• Studies With Functionally Substituted Heteroaromatics: A Novel Route for the Synthesis of 1-Aryl-6-oxopyridazinones, 1-Arylpyridazine-6-imines and 1-Aryl-6-imino-4-pyridazinals
  作者：Fatima Al-Omran、Mervat Mohammed Abdel Khalik、Adel Abou-Elkhair、Mohammed Hilmy Elnagdi

  DOI：10.1055/s-1997-1512

  日期：1997.1

  Aryldiazonium salts couple with the 3-dimethylamino-1-substituted enones 1 a-c to yield 2-arylhydrazono-3-oxo-3-substituted-propanals which are excellent precursors for the synthesis of pyridazinones. The coupling reaction of 2-cyano-5-dimethylamino-3-substituted-penta-2,4-dienonitrile 12 a-b with benzene diazonium salts in ethanolic sodium hydroxide gives the pyridazinals 13 a, b.

  Aryldiazonium 盐与3-二甲基氨基-1-取代烯酮 1 a-c 反应，生成2-芳基肼佐-3-氧代-3-取代丙醛，这些化合物是合成吡嗪酮的优秀前体。2-氰基-5-二甲基氨基-3-取代戊-2,4-二烯腈 12 a-b 与苯二氮盐在乙醇钠氢氧化物中反应，生成吡嗪醛 13 a, b。
• <i>N</i>-Azolylmethyl ketones as building blocks in heterocyclic synthesis: Synthesis of new polyfunctionally substituted azolylarylazophenols, azolylpyridones and azolylthiophenes
  作者：Balkis Al-Saleh、Morsy Ahmed El-Apasery、Mervat Mohammed Abdelkhalik、Mohammed Hilmy Elnagdi

  DOI：10.1002/jhet.5570400125

  日期：2003.1

  2-arylhydrazonopropanals 3a-c to yield polyfunctionally substituted azolylarylazophenols 5 and 8. The reaction of 1b and 2 with phenylisothiocyanate in the presence of α-haloketones afforded the azolylthiophenes 12a,b and 13a,b. The reaction of 20 with α-haloketone afforded 5-benzotriazol-1-yl-6-methyl-2-(2-oxopropylsulfanyl)nicotinonitrile 21 that was utilized as building blocks for the synthesis of condensed

  标题化合物1a-b和2与2-芳基肼基丙醛3a-c反应，得到多官能取代的偶氮基芳基偶氮苯酚5和8。1b和2与苯基异硫氰酸酯在α-卤代酮存在下反应，得到偶氮基噻吩12a，b和13a，b。 。20与α-卤代酮的反应提供了5-苯并三唑-1-基-6-甲基-2-（2-氧丙基硫基）烟腈21，其被用作合成缩合吡啶的结构单元。将化合物21与二甲基甲酰胺二甲基缩醛缩合，得到噻吩并[2，3 - b ]吡啶-3-基-N，N-二甲基甲am衍生物22。将其进一步用氢化钠环化成1 H-二硫代[2，3- b]。4,5- b'] dipyridin-4-one衍生物23。
• Chemistry of 2-Arylhydrazonopropanals: Novel Synthesis of 1,6-Dihydropyridazines and 5-Heteroaryl Substituted Pyrazolo[1,5-a]Pyrimidines and Pyrazolo[3,4-b]Pyridines
  作者：Mervat Mohammed Abdel-Khalik、Samia Michel Agamy、Mohammed Hilmy Elnagdi

  DOI：10.1055/s-2001-17522

  日期：——

  The reaction of 2-arylhydrazonopropanals 1a-d with dimethyl acetylenedicarboxylate in anhydrous dichloromethane in the presence of triphenylphosphine afforded 1,6-dihydropyridazines 2a-d. Compound 1a reacted with dimethyl acetylenedicarboxylate in refluxing acetic acid yielding the corresponding Michael adduct 4. Whereas compound 1d failed to react in acetic acid with diphenylacetylene, its reaction with the same reagent in anhydrous dichloromethane in the presence of triphenylphosphine afforded the Michael adduct 3. Compounds 2b-d reacted with hydrazine hydrate affording the corresponding pyridazino[3,4-d]pyr-idazines 6b-d. 2-Arylhydrazonopropanals 1a,b reacted with 5-methyl-1H-pyrazol-3-amine in ethanol yielding the corresponding condensation products 8a,b, which cyclized to the 7-substituted 2-methyl-6-phenylazopyrazolo[1,5-a]pyrimidines 9a,b and 4-substituted 3-methyl-5-phenylazopyrazolo[3,4-b]pyridines 10a,b on refluxing in acetic acid. 2-Phenylhydrazonopropanal 1a reacted with p-benzoquinone yielding the resorcinol derivative 12.

  2-芳基亚肼基丙醛1a-d与乙炔二甲酸二甲酯在无水二氯甲烷中在三苯基膦存在下反应得到1,6-二氢哒嗪2a-d。化合物1a与乙炔二甲酸二甲酯在回流乙酸中反应，得到相应的迈克尔加合物4。虽然化合物1d未能在乙酸中与二苯乙炔反应，但其在无水二氯甲烷中在三苯基膦存在下与相同试剂反应，得到迈克尔加合物3。 化合物2b-d与水合肼反应，得到相应的哒嗪并[3,4-d]哒嗪6b-d。 2-芳基亚肼基丙醛1a,b与5-甲基-1H-吡唑-3-胺在乙醇中反应，生成相应的缩合产物8a,b，其环化为7-取代的2-甲基-6-苯基偶氮吡唑并[1,5-a ]嘧啶9a，b和4-取代的3-甲基-5-苯基偶氮吡唑并[3，4-b]吡啶10a，b在乙酸中回流。 2-苯基腙丙醛 1a 与对苯醌反应，生成间苯二酚衍生物 12。
• Gas-phase pyrolysis in organic synthesis. Part 3: Novel cyclization of 2-arylhydrazonopropanals into cinnolines1
  作者：Ajith Kumar、Nouria A. Al-Awadi、Mohamed H. Elnagdi、Yehia A. Ibrahim、Kamini Kaul

  DOI：10.1002/kin.1035

  日期：2001.7

  3-oxo-3-aryl-2-arylhydrazonopropanals (1) have been converted under thermal gas-phase conditions cleanly into cinnolines (2). A plausible mechanism is suggested to account for this transformation based on the kinetics and products of reaction. © 2001 John Wiley & Sons, Inc. Int J Chem Kinet 33: 402–406, 2001

  3-oxo-3-aryl-2-arylhydrazonopropanals (1) 已在热气相条件下干净地转化为 cinnolines (2)。基于动力学和反应产物，提出了一种合理的机制来解释这种转变。© 2001 John Wiley & Sons, Inc. Int J Chem Kinet 33: 402–406, 2001