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Synthesis of Anionic Phosphorus-Containing Heterocycles by Intramolecular Cyclizations Involving N-Functionalized Phosphinecarboxamides

机译：通过涉及N-功能化膦酰胺的分子内环化反应合成含磷杂环杂环化合物

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摘要

We report that the 2-phosphaethynolate anion (PCO⁻) reacts with propargylamines in the presence of a proton source to afford novel N-derivatized phosphinecarboxamides bearing alkyne functionalities. Deprotonation of these species gives rise to novel five- and six-membered anionic heterocycles resulting from intramolecular nucleophilic attack of the resulting phosphide at the alkyne functionality (via 5-exo-dig or 6-endo-dig cyclizations, respectively). The nature of the substituents on the phosphinecarboxamide can be used to influence the outcome of these reactions. This strategy represents a unique approach to phosphorus-containing heterocylic systems that are closely related to known organic molecules with interesting bio-active properties.

机译：我们报告2-质子甲酸酯阴离子（PCO ^{-）与炔丙基胺在质子源的存在下反应，以提供具有炔官能团的新型N-衍生化膦酰胺。这些物质的去质子化产生了新的五元和六元阴离子杂环，这是由于分子内的亲核攻击了炔基官能团（分别通过5-exo-dig或6-endo-dig环化作用）所产生的磷化物所致。膦羧酰胺上取代基的性质可用于影响这些反应的结果。该策略代表了一种独特的方法，用于处理含磷杂环系统，该系统与具有有趣生物活性的已知有机分子密切相关。}

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期刊名称 Wiley-Blackwell Online Open
作者
Thomas P Robinson; Jose M Goicoechea;
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作者单位

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年(卷),期 -1(21),15
年度 -1
页码 5727–5731
总页数 5
原文格式 PDF
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中图分类
关键词
2-phosphaethynolate anion heterocycles phosphides phosphorus propargyl-phosphines;

机译：2-磷胸苷酸根阴离子;杂环;磷化物;磷;炔丙基膦;

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1. Synthesis of Anionic Phosphorus-Containing Heterocycles by Intramolecular Cyclizations Involving N-Functionalized Phosphinecarboxamides [J] . Robinson Thomas P., Goicoechea Jose M. Chemistry: A European journal . 2015,第15期

机译：涉及N功能化的膦酰胺类化合物的分子内环化合成阴离子含磷杂环。
2. Substituent Enabled Divergent Synthesis of N-Heterocycles: a Metal Carbene Approach Involving Intramolecular Carbene Interception [J] . Xu Hua-Dong, Xu Ke, Jia Zhi-Hong, Asian Journal of Organic Chemistry . 2014,第11期

机译：N杂环取代基使能发散合成：涉及分子内碳烯截留的金属碳烯方法
3. SYNTHESIS OF HETEROCYCLES USING THE INTRAMOLECULAR HECK REACTION INVOLVING A 'FORMAL'ANTI-ELIMINATION PROCESS [J] . Ikeda Masazumi, Bialy Serry A.A.El Heterocycles: An International Journal for Reviews and Communications in Heterocyclic Chemistry . 1999,第8期

机译：利用涉及“正式”反电消除过程的分子内赫克反应合成杂环
4. Solvent-Controlled Cascade Reaction of Ugl/Pd-Catalyzed Intramolecular Divergent C-H Fumctionalization for Regies elective Synthesis of Cyclopropanated N-Heterocycles [C] . Tianyi Shang, Yan Pan, Zhong Chen International Conference on Advanced Composite Materials and Manufacturing Engineering . 2020

机译：UGL / PD催化的溶剂控制级联反应UGL / PD催化分子内发散的C-H富脉冲率的调节选择性合成环丙烷的N-杂环
5. Microwave-assisted synthesis of biologically important 5-membered heterocycles via intramolecular cyclization of ketones. [D] . Rais, Afsha. 2009

机译：通过酮的分子内环化的微波辅助合成生物上重要的5元杂环。
6. Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization [O] . Mickael Choury, Alexandra Basilio Lopes, Gaëlle Blond, 2020

机译：通过过渡金属催化的分子分子化合成中尺寸杂环
7. Synthesis of erythrina and related alkaloids. XXII. Intramolecular cyclization approach. 1): New synthetic route to erythrinan and related heterocycles and synthesis of (.+-.)-3-demethoxy-erythratidinone. [O] . Yoshisuke TSUDA, Yuki SAKAI, Akira NAKAI, 1990

机译：红素和相关生物碱的合成。 XXII。分子内的环化方法。 1）：新的红绿腺和相关杂环的新合成途径和合成（。+ - 。） - 3-脱甲氧基赤素酮。

Synthesis of Anionic Phosphorus-Containing Heterocycles by Intramolecular Cyclizations Involving N-Functionalized Phosphinecarboxamides

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