Heteroaromatic Belts through Fold-in Synthesis: Mechanistic Insights into a Macrocycle-Templated Friedel-Crafts Alkylation

Kondratowicz Mateusz; Mysliwiec Damian; Lis Tadeusz; Stepien Marcin

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Heteroaromatic Belts through Fold-in Synthesis: Mechanistic Insights into a Macrocycle-Templated Friedel-Crafts Alkylation

机译：通过折叠合成的杂芳族带：机械洞察到大环模板化的Friedel-Crafts烷基化

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摘要

Direct alkylation of 9,9,9-triethyl[2.2.2](2,7)carbazolophane with dimethoxymethane or paraformaldehyde affords a belt-like heteroaromatic structure, which forms as a kinetic product in acid-catalyzed condensations. In a competing, thermodynamically favored process, polymeric structures are formed by a largely regioselective condensation of stereochemically rigid semi-belts. The relationship between these reactivity routes is rationalized in terms of strain release and differential reversibility of consecutive condensation steps.

机译：9,9,9-三乙基[2.2.2]（2,7）咔唑烷与二甲氧基甲烷或低聚甲醛的直接烷基化提供了带状杂芳族结构，其在酸催化的缩合反应中作为动力学产物形成。在竞争性的，热力学上有利的过程中，聚合物结构是通过立体化学刚性半带的大部分区域选择性缩合形成的。这些反应路线之间的关系在应变释放和连续缩合步骤的差异可逆性方面得到了合理化。

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《Chemistry: A European journal》 |2014年第46期|共5页
作者
Kondratowicz Mateusz; Mysliwiec Damian; Lis Tadeusz; Stepien Marcin;
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正文语种 eng
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cyclophanes; electrophilic substitution; fused ring systems; nitrogen heterocycles; polymers;

机译：环烷;亲电取代;稠环系统;氮杂环;聚合物;

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1. Heteroaromatic Belts through Fold-in Synthesis: Mechanistic Insights into a Macrocycle-Templated Friedel-Crafts Alkylation [J] . Kondratowicz Mateusz, Mysliwiec Damian, Lis Tadeusz, Chemistry: A European journal . 2014,第46期

机译：通过折叠合成的杂芳族带：机械洞察到大环模板化的Friedel-Crafts烷基化
2. Development of a Selective Friedel-Crafts Alkylation Surrogate: Safe Operating Conditions through Mechanistic Understanding [J] . Robert N. Bream, David G. Hulcoop, Steve J. Gooding Organic process research & development . 2012,第12期

机译：选择性Friedel-Crafts烷基化替代物的开发：通过机理理解来确保安全的操作条件
3. Diarylprolinol silyl ether catalyzed asymmetric friedel-crafts alkylation of indoles with α,β-unsaturated aldehydes: Enhanced enantioselectivity and mechanistic investigations [J] . Shi Z.-H., Sheng H., Yang K.-F., European journal of organic chemistry . 2011,第1期

机译：二芳基脯氨醇甲硅烷基醚催化α，β-不饱和醛与吲哚的不对称friedel-crafts烷基化：增强的对映选择性和机理研究
4. Enantioselective Friedel-Crafts Alkylation Reaction of Indoles with Non-activated β-Alkyl-β-Nitrostyrenes Catalyzed by Chiral BINOL Phosphates [C] . Mio Kaneko, Ignacio Ibanez Sanchez, Takahiko Akiyama 日本化学会春季年会講演予稿集 . 2018

机译：用手性甲醇磷酸盐催化的非活化β-烷基-β-硝化吲哚的对映选择性的Friedel-Crafts抗体的烷基化反应
5. Part I. The synthesis of 5-hydroxymethyl-3-nucleobase-2-pyrrolidinones as potential anti-HIV compounds. Part II. Conducting polymers as chemical reagents: The use of poly-(3,4-ethylenedioxy thiophene) in the Friedel-Crafts alkylation of aromatic rings with alcohols. [D] . D'Angelo, John Gaetano. 2005

机译：第一部分：5-羟甲基-3-核碱基-2-吡咯烷酮类化合物作为潜在的抗HIV化合物的合成。第二部分导电聚合物作为化学试剂：聚（3,4-亚乙二氧基噻吩）在芳香醇与醇的弗瑞德-克来福特烷基化反应中的用途。
6. A Cycloisomerization/Friedel-Crafts Alkylation Strategy for the Synthesis of Pyrano34-bindoles [O] . Matthew R. Medeiros, Scott E. Schaus, John A. Porco Jr. -1

机译：甲环异构/的Friedel-Crafts烷基化策略吡喃并34-B吲哚的合成
7. Direct Synthesis of 2D-Hexagonal Mesoporous Iron Silicate and its Catalytic Activity for Selective Friedel-Crafts Alkylation [O] . Swapan K. Das 2012

机译：直接合成2D-六边形介孔铁硅酸盐及其催化活性的选择性Friedel-Crafts烷基化

Heteroaromatic Belts through Fold-in Synthesis: Mechanistic Insights into a Macrocycle-Templated Friedel-Crafts Alkylation

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