1-(2-benzenesulfonyl-2-diazoacetyl)pyrrolidin-2-one | 185198-40-7

• 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: 1-(2-benzenesulfonyl-2-diazoacetyl)pyrrolidin-2-one
• 英文别名: 1-(phenylsulfonyldiazoacetyl)pyrrolidin-2-one；2-Pyrrolidinone, 1-[diazo(phenylsulfonyl)acetyl]-；1-[2-(benzenesulfonyl)-2-diazoacetyl]pyrrolidin-2-one
• CAS: 185198-40-7
• 化学式: C₁₂H₁₁N₃O₄S
• 分子量: 293.303
• InChiKey: QPXINKPAZPNZCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  81.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-benzenesulfonyl-2-diazoacetyl)pyrrolidin-2-one 在 rhodium(II) acetate dimer 、 四(三苯基膦)钯 、 三乙胺 、 lithium chloride 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 14.0h， 生成 8-phenylsulfonyl-6-(4-methoxyphenyl)-7-methyl-2,3-dihydro-1H-indolizin-5-one
  参考文献：
  名称：

  An Isomünchnone-Based Method for the Synthesis of Highly Substituted 2(1H)-Pyridones

  摘要：

  1-(Benzenesulfonyl-diazoacetyl)-pyrrolidin-2-one was prepared by a diazo transfer of 1-(benzenesulfonylacetyl)-pyrrolidin-2-one with p-acetamidobenzenesulfonyl azide and triethylamine. Treatment; of the diazoimide with a catalytic quantity of rhodium(II) acetate resulted in the formation of an isomunchnone dipole, which underwent bimolecular trapping with various dipolarophiles in high yield. The initially formed cycloadducts were not isolable or observed, as they all readily underwent ring opening to give the 3-hydroxy-2(1H)-pyridone ring system. The 3-hydroxy-2(1H)-pyridones were readily converted to the corresponding triflates, which function as suitable substrates in various types of palladium-catalyzed cross-coupling reactions. Commercial tetrakis(triphenylphoshine)palladium was found to be a particularly effective catalyst for the cross-coupling with aryl, vinyl, and acetylenic partners. An application of the method to the synthesis of the indolizidine alkaloid (+/-)-ipalbidine was carried out in eight steps in 17% overall yield. The angiotensin-converting enzyme inhibitor (-)-A58365A was also synthesized by a process based on the [3 + 2]-cycloaddition reaction of a phenylsulfonyl substituted isomunchnone intermediate. The starting material for this process was prepared from L-pyroglutamic acid and involved using a diazo phenylsulfonyl substituted pyrrolidine imide. Treatment of the diazoimide with Rh-2(OAc)(4) in the presence of methyl vinyl ketone afforded a 3-hydroxy-2-pyridone derivative, which was subsequently converted to the ACE inhibitor in six additional steps.

  DOI：

  10.1021/jo9911600
• 作为产物：
  描述：

  (苯磺酰)乙酸 在 草酰氯 、 4-乙酰氨基苯磺酰叠氮 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 乙腈 、 苯 为溶剂， 反应 10.0h， 生成 1-(2-benzenesulfonyl-2-diazoacetyl)pyrrolidin-2-one
  参考文献：
  名称：

  An Isomünchnone-Based Method for the Synthesis of Highly Substituted 2(1H)-Pyridones

  摘要：

  1-(Benzenesulfonyl-diazoacetyl)-pyrrolidin-2-one was prepared by a diazo transfer of 1-(benzenesulfonylacetyl)-pyrrolidin-2-one with p-acetamidobenzenesulfonyl azide and triethylamine. Treatment; of the diazoimide with a catalytic quantity of rhodium(II) acetate resulted in the formation of an isomunchnone dipole, which underwent bimolecular trapping with various dipolarophiles in high yield. The initially formed cycloadducts were not isolable or observed, as they all readily underwent ring opening to give the 3-hydroxy-2(1H)-pyridone ring system. The 3-hydroxy-2(1H)-pyridones were readily converted to the corresponding triflates, which function as suitable substrates in various types of palladium-catalyzed cross-coupling reactions. Commercial tetrakis(triphenylphoshine)palladium was found to be a particularly effective catalyst for the cross-coupling with aryl, vinyl, and acetylenic partners. An application of the method to the synthesis of the indolizidine alkaloid (+/-)-ipalbidine was carried out in eight steps in 17% overall yield. The angiotensin-converting enzyme inhibitor (-)-A58365A was also synthesized by a process based on the [3 + 2]-cycloaddition reaction of a phenylsulfonyl substituted isomunchnone intermediate. The starting material for this process was prepared from L-pyroglutamic acid and involved using a diazo phenylsulfonyl substituted pyrrolidine imide. Treatment of the diazoimide with Rh-2(OAc)(4) in the presence of methyl vinyl ketone afforded a 3-hydroxy-2-pyridone derivative, which was subsequently converted to the ACE inhibitor in six additional steps.

  DOI：

  10.1021/jo9911600

文献信息

• 1,3-Dipolar Cycloaddition Chemistry for the Preparation of Novel Indolizinone-Based Compounds
  作者：Edwin M. Mmutlane、Joel M. Harris、Albert Padwa

  DOI：10.1021/jo0511492

  日期：2005.9.1

  7-b]indol-5-ones. To prepare furano-fused indolizinones, methyl 6-hydroxy-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate was etherified with different allyl halides, and the resultant allyl ethers were subjected to a thermal Claisen rearrangement to give the corresponding methyl 7-allyl-6-hydroxy-5-oxo-1,2,3,4-tetrahydroindolizine-8-carboxylates. Cyclization under Wacker oxidation conditions afforded

  由5-（氧代-6）-三氟甲磺酰氧基-1,2,3,5-四氢吲哚嗪-8-羧酸甲酯开始，通过Rh（II）催化的1-（2-苯磺酰基-2）的1,3-偶极环加成反应获得（重氮基乙酰基）吡咯烷-2-酮和丙烯酸甲酯，可有效制备几种吲哚和呋喃并熔的吲哚并酮。在第一种情况下，三氟甲磺酸酯与各种取代的苯胺的钯介导的C-N偶联提供了所需的5-氧代-6-（芳基氨基）-1,2,3,5-四氢吲哚嗪-8-羧酸甲酯高产。6-（2-溴苯基氨基）-5-氧-1,2,3,5-四氢吲哚嗪-8-羧酸甲酯及其脱羧类似物6-（2-溴苯基氨基）-2,3-二氢-1 H-吲哚izin-5-one，以极高的产率合成，并经过分子内Heck环化反应，得到1,2,3,6-tetrahydroindolizino [6,7- b ] indol-5-ones。为了制备呋喃并稠合的吲哚嗪酮，将6-羟基-5-氧代-1,2,3,5-四氢吲哚嗪-8-羧酸甲酯与不
• [EN] PYRIDINYL BASED APOPTOSIS SIGNAL-REGULATION KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASE DE RÉGULATION DU SIGNAL APOPTOTIQUE À BASE DE PYRIDINYLE
  申请人：FRONTHERA U S PHARMACEUTICALS LLC

  公开号：WO2018151830A1

  公开（公告）日：2018-08-23

  Apoptosis signal-regulating kinase 1 (ASK1) activation and signaling have been reported to play an important role in a broad range of diseases including neurodegenerative, cardiovascular, inflammatory, autoimmunity and metabolic disorders. Disclosed herein is the synthesis of pyridinyl derived therapeutic agents that function as inhibitors of ASK 1 as well as their pharmaceutical compositions and methods of use.

  细胞凋亡信号调节激酶1（ASK1）的激活和信号传导据报道在包括神经退行性、心血管、炎症、自身免疫和代谢紊乱等广泛疾病中发挥重要作用。本文披露了一种以吡啶基衍生的治疗剂的合成，其作为ASK1的抑制剂以及它们的药物组合物和使用方法。
• Synthesis of a 2(1<i>H</i>)-Pyridone Library via Rhodium-Catalyzed Formation of Isomunchones
  作者：Subhasis De、Lu Chen、Shuxing Zhang、Scott R. Gilbertson

  DOI：10.1021/co400067q

  日期：2013.7.8

  Through the use of the dipolar cycloaddition of isomunchones with olefins the 2(1H)-pyridone ring system has been synthesized.(1) The use of different cyclization partners followed by diversification of the initial scaffold has provded libraries of 4-hydroxy-2(1H)-pyridones. There are no examples of this ring system in either PubChem or the MLSMR

  通过异丁烯与烯烃的偶极环加成反应，合成了2（1 H）-吡啶酮环系统。（1）使用不同的环化配偶体，随后使初始支架多样化，提供了4-hydroxy-2库（1 H）-吡啶酮。PubChem或MLSMR中都没有此环系统的示例
• New Synthetic Route to 2-Pyridones and Its Application toward the Synthesis of (±)-Ipalbidine
  作者：Scott M. Sheehan、Albert Padwa

  DOI：10.1021/jo961690l

  日期：1997.2.1
• An Isomünchnone-Based Method for the Synthesis of Highly Substituted 2(1<i>H</i>)-Pyridones
  作者：Albert Padwa、Scott M. Sheehan、Christopher S. Straub

  DOI：10.1021/jo9911600

  日期：1999.11.1

  1-(Benzenesulfonyl-diazoacetyl)-pyrrolidin-2-one was prepared by a diazo transfer of 1-(benzenesulfonylacetyl)-pyrrolidin-2-one with p-acetamidobenzenesulfonyl azide and triethylamine. Treatment; of the diazoimide with a catalytic quantity of rhodium(II) acetate resulted in the formation of an isomunchnone dipole, which underwent bimolecular trapping with various dipolarophiles in high yield. The initially formed cycloadducts were not isolable or observed, as they all readily underwent ring opening to give the 3-hydroxy-2(1H)-pyridone ring system. The 3-hydroxy-2(1H)-pyridones were readily converted to the corresponding triflates, which function as suitable substrates in various types of palladium-catalyzed cross-coupling reactions. Commercial tetrakis(triphenylphoshine)palladium was found to be a particularly effective catalyst for the cross-coupling with aryl, vinyl, and acetylenic partners. An application of the method to the synthesis of the indolizidine alkaloid (+/-)-ipalbidine was carried out in eight steps in 17% overall yield. The angiotensin-converting enzyme inhibitor (-)-A58365A was also synthesized by a process based on the [3 + 2]-cycloaddition reaction of a phenylsulfonyl substituted isomunchnone intermediate. The starting material for this process was prepared from L-pyroglutamic acid and involved using a diazo phenylsulfonyl substituted pyrrolidine imide. Treatment of the diazoimide with Rh-2(OAc)(4) in the presence of methyl vinyl ketone afforded a 3-hydroxy-2-pyridone derivative, which was subsequently converted to the ACE inhibitor in six additional steps.