ethyl pyrido[2,1-a]isoindole-6-carboxylate | 1111165-53-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: ethyl pyrido[2,1-a]isoindole-6-carboxylate
• 英文别名: Ethyl pyrido[1,2-b]isoindole-6-carboxylate；ethyl pyrido[1,2-b]isoindole-6-carboxylate
• CAS: 1111165-53-7
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: XVLCGLJWVFSCTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl 2-diazo-2-(2-(pyridin-2-yl)phenyl)acetate 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.33h， 以94%的产率得到ethyl pyrido[2,1-a]isoindole-6-carboxylate
  参考文献：
  名称：

  通过重氮化反应合成吡啶并异吲哚，然后在一锅中由吡啶基芳基乙酸酯进行分子内环化

  摘要：

  通过使用4-甲基苯磺酰基叠氮化物和1,8-二氮杂双环[5.4.0]十一碳-7-烯进行重氮化，然后通过消除铜下的氮分子进行分子内环化，已开发出一种强大的合成方法，用于从吡啶基芳基乙酸酯中合成各种吡啶基异吲哚。II）一锅法中三氟甲磺酸盐催化的条件。在无金属条件或催化条件[1.0 mol％三氟甲磺酸铜（II）铜，25°C]下，重氮底物也有效地进行了分子内环化反应，以良好的产率获得了吡啶异吲哚。

  DOI：

  10.1002/adsc.201500433

文献信息

• A [4 + 1] Cyclative Capture Access to Indolizines via Cobalt(III)-Catalyzed Csp²–H Bond Functionalization
  作者：Xun Chen、Xinwei Hu、Yuanfu Deng、Huanfeng Jiang、Wei Zeng

  DOI：10.1021/acs.orglett.6b02421

  日期：2016.9.16

  A Co(III)-catalyzed [4 + 1] cycloaddition of 2-arylpyridines or 2-alkenylpyridines with aldehydes through Csp2–H bond activation has been developed. This protocol provides a facile approach to structurally diverse indolizines including benzoindolizines with a broad range of functional group tolerance.

  通过Csp 2 -H键活化，已开发出了Co（III）催化2-芳基吡啶或2-烯基吡啶与醛的[4 +1]环加成反应。该协议为结构多样的吲哚嗪提供了一种简便的方法，包括具有广泛官能团耐受性的苯并吲哚并嗪。
• Multicomponent reactions of pyridines, α-bromo carbonyl compounds and silylaryl triflates as aryne precursors: a facile one-pot synthesis of pyrido[2,1-a]isoindoles
  作者：Xian Huang、Tiexin Zhang

  DOI：10.1016/j.tetlet.2008.10.118

  日期：2009.1

  Multicomponent reactions (MCRs) involving pyridines, α-bromo ketones, and silylaryl triflates as aryne precursors were investigated. The reactions could also be extended to isoquinoline or α-bromo ethyl acetate. Substituted pyrido[2,1-a]isoindoles or isoindolo[2,1-a]isoquinolines could be obtained from this routine, which may have potential applications in antitumor drugs and fluorescent material fields

  研究了涉及吡啶，α-溴代酮和甲硅烷基芳基三氟甲磺酸酯作为芳烃前体的多组分反应（MCR）。反应也可扩展至异喹啉或α-溴乙酸乙酯。取代的吡啶并[2,1-一个]异吲哚异吲哚或[2,1-一个]异喹啉类可以从该程序中，其可以具有在抗肿瘤药物和荧光材料领域的潜在应用而获得。
• 신규한 피리도아이소인돌 유도체의 제조방법
  申请人：KNU-Industry Cooperation Foundation 강원대학교산학협력단(220040088571) BRN ▼221-82-10213

  公开号：KR20170109709A

  公开（公告）日：2017-10-10

  본 발명은 약학, 천연물, 형광 물질, 염색 물질과 같은 다양한 분야에서 사용되는 주요 골격 구조로 이용될 수 있는 피리도아이소인돌 유도체의 제조방법에 관한 것으로, 다양한 친핵체와 반응 할 수 있는 카벤 유도체를 이용하여 다이아조아세테이트로부터 구리촉매 존재 하에 또는 구리촉매 없이 가열만을 통해 효과적이고 보다 용이하게 피리도아이소인돌 유도체의 제조방법을 제공한다. 또한 아세테이트 유도체에 염기성 촉매, 아지드 유도체를 사용하여 diazotization을 진행한 후 Cu(OTf) 촉매하에 질소의 제거반응을 통한 분자내 고리화 반응을 one-pot으로 진행 시켜 피리도인돌유도체의 효율적인 제조방법을 제공한다.

  本发明涉及一种制备可用作药学、天然物、荧光物质、染料等多个领域的主要骨架结构的吡啶并异吲哚衍生物的制备方法，利用多种亲核试剂与卡宾衍生物反应，通过在铜催化下或仅通过加热而无需铜催化的条件下，从二氮基乙酸酯中有效且更容易地制备吡啶并异吲哚衍生物。此外，本发明还提供了一种高效的制备方法，通过使用碱性催化剂和叠氮化合物对乙酸酯衍生物进行重氮化反应，然后在Cu(OTf)催化下进行分子内环化反应，以一步完成吡啶并异吲哚衍生物的制备。
• Light-Induced Generation and Cycloaddition Reactions of Benzyne: Synthesis of Naphthoxindoles E and Annulated Indolizines
  作者：Haya Khan、Dhiraj Barman、Subhabrata Sen

  DOI：10.1021/acs.joc.4c00257

  日期：——

  dienophiles in numerous cycloaddition reactions. However, in situ generation of benzyne involves either base-mediated thermal reactions, low-temperature conditions, or metal-catalyzed reactions of substituted arenes. This limits the applicability of benzynes as suitable dipolarophiles in cycloaddition reactions. Herein, we have reported a UVA (365 nM)-induced in situ generation of benzynes (from triazenyl

  由于其高亲电子性质，苯炔在许多环加成反应中充当反应性亲二烯体。然而，苯炔的原位生成涉及碱介导的热反应、低温条件或取代芳烃的金属催化反应。这限制了苯炔作为环加成反应中合适的亲偶极试剂的应用。在此，我们报道了 UVA (365 nM) 诱导原位生成苯炔（来自三氮烯基苯甲酸），随后与适当的反应伙伴（如 N）发生 [4 + 2] Diels-Alder 和 [3 + 2] 环加成反应-保护的亚烷基羟吲哚羧酸盐和吡啶鎓叶立德分别以中等至优异的产率提供萘吲哚E和吡啶并[2,1- a ]异吲哚。反应在室温和无试剂反应条件下进行。这些构件中的每一个都具有药学相关性；因此，这凸显了获取此类化合物的有趣策略。
• Cobalt-Catalyzed Carbonylative Cyclization of Pyridinyl Diazoacetates for the Synthesis of Pyridoisoquinolinones
  作者：Yonghyeon Baek、Sunghwa Kim、Bongkeun Jeon、Phil Ho Lee

  DOI：10.1021/acs.orglett.5b03340

  日期：2016.1.4

  Dicobalt octacarbonyl-catalyzed carbonylative cyclization of pyridinyl diazoacetates is developed for the synthesis of pyridoisoquinolinones under mild conditions (room temperature) in a carbon monoxide atmosphere. Moreover, a synthetic method for various pyridoisoquinolinones from ethylp-yridinyl aryl acetates is demonstrated through diazotization using TsN3 and DBU followed by Co-catalyzed carbonylation to generate ketene intermediates, which can subsequently undergo intramolecular cyclization under mild conditions in a carbon monoxide atmosphere in a semi-one-pot fashion.