Convenient Synthesis of Highly Functionalized, 3,4-Disubstituted Indole Building Blocks

Sonia Miranda; Pilar López-Alvarado; Carmen Avenda?o; J. Carlos Menéndez

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Convenient Synthesis of Highly Functionalized, 3,4-Disubstituted Indole Building Blocks

机译：方便合成高度官能化的3,4-二取代的吲哚结构单元

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Several 3,4-disubstituted indole building blocks were synthesized, containing a one-carbon functional group at C-4 and a three-carbon chain bearing at least one ω functional group. A C-4 functionalized indole derivative was prepared by application of the Leimgruber-Batcho reaction. Several three-carbon chains were subsequently installed at the indole C-3 position. In the first strategy employed, a Mannich reaction was followed by the creation of a C-C bond by phosphine-induced generation of a 3-methyleneindolenine species, which was trapped by diethyl malonate. Alternatively, a Vilsmeier formylation at C-3 was followed by Knoevenagel or Wittig reactions or by treatment with ethyl diazoacetate in the presence of a Lewis acid. Direct introduction of the three-carbon chain at C-3 using a Lewis acid-catalyzed Michael reaction was also achieved. Further functionalization of the benzylic position attached to C-4 by attachment of a nitro group was carried out, but preparation of a tricyclic welwistatin fragment by intramolecular nitroalkane acylation or intramolecular Henry reactions was not possible.

机译：合成了几个3,4-二取代的吲哚结构单元，在C-4处含有一个碳原子的官能团和一个带有至少一个ω官能团的三碳链。通过应用Leimgruber-Batcho反应制备了C-4官能化的吲哚衍生物。随后在吲哚C-3位置安装了几条三碳链。在采用的第一种策略中，曼尼希反应之后是膦诱导的3-亚甲基吲哚烯碱物种的生成，从而形成了C-C键，后者被丙二酸二乙酯捕获。备选地，在C-3处的维斯迈尔甲酰化之后进行Knoevenagel或Wittig反应，或在路易斯酸存在下用重氮乙酸乙酯处理。还实现了使用路易斯酸催化的迈克尔反应在C-3处直接引入三碳链。通过连接硝基进一步使连接至C-4的苄基官能化，但是不可能通过分子内硝基链烷酰化或分子内亨利反应制备三环welwistatin片段。

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《The Open Organic Chemistry Journal》 |2007年第1期|共12页
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Sonia Miranda; Pilar López-Alvarado; Carmen Avenda?o; J. Carlos Menéndez;
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1. Highly versatile solid phase synthesis of biofunctional 4-aryl-3,4-dihydropyrimidines using resin-bound isothiourea building blocks and multidirectional resin cleavage. [J] . Kappe CO Bioorganic and Medicinal Chemistry Letters . 2000,第1期

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2. Erratum: Stereoselective synthesis of unsymmetrical β,β- diarylacrylates by a Heck-Matsuda reaction: Versatile building blocks for asymmetric synthesis of β,β-diphenylpropanoates, 3-aryl-indole, and 4-aryl-3,4-dihydro-quinolin-2-one and formal synthesis of (-)-indatraline (The Journal of Organic Chemistry (2011) 76 (857-869) DOI: 10.1021/jo102134v) [J] . Taylor J.G., Correia C.R.D. The Journal of Organic Chemistry . 2012,第11期

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3. Stereoselective synthesis of unsymmetrical β,β-diarylacrylates by a heck-matsuda reaction: Versatile building blocks for asymmetric synthesis of β,β-diphenylpropanoates, 3-Aryl-indole, and 4-Aryl-3,4-dihydro- quinolin-2-one and formal synthesis of (-)-indatraline [J] . Taylor J.G., Correia C.R.D. The Journal of Organic Chemistry . 2011,第3期

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4. Functionalization of Amide-Building Blocks with endo-Gd-N-Cluster-Fullerene for Synthesis of BioShuttle Conjugates as cell-specific intracellular MR-Contrast Agents [C] . Pipkorn R, Wiessler M, Dunsch L, European Conference on Chemistry for Life Sciences . 2011

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机译：寻求一种改进的成环方法：I. 1,1-二卤-1-乙烯基乙烯基环丙烷-有用的结构单元，用于立体选择性合成高度官能化的环戊烷。二。进一步尝试合成天然的布雷菲德丁类
6. Towards a facile and convenient synthesis of highly functionalized indole derivatives based on Multi-Component Reactions [O] . Constantinos G. Neochoritis, Alexander Dömling -1

机译：致力于基于多组分反应轻松便捷地合成高度官能化的吲哚衍生物
7. Synthesis of 3,4-disubstituted furans and 3-substituted furans using 3,4-bis(tri-n-butylstannyl)furan and 3-(tri-n-butylstainnyl)furan as building blocks. [O] . 1993

机译：使用3,4-双（三正丁基甲锡烷基）呋喃和3-（三正丁基苯乙烯基）呋喃作为结构单元合成3,4-二取代的呋喃和3-取代的呋喃。

Convenient Synthesis of Highly Functionalized, 3,4-Disubstituted Indole Building Blocks

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