Vinylic MIDA Boronates: New Building Blocks for the Synthesis of Aza-Heterocycles

Llona-Minguez Sabin; Desroses Matthieu; Ghassemian Artin; Jacques Sylvain A.; Eriksson Lars; Isacksson Rebecka; Koolmeister Tobias; Stenmark Pal; Scobie Martin; Helleday Thomas

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Vinylic MIDA Boronates: New Building Blocks for the Synthesis of Aza-Heterocycles

机译：乙烯基MIDA硼酸酯：合成氮杂杂环的新构件

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A two-step synthesis of structurally diverse pyrrole-containing bicyclic systems is reported. ortho-Nitro-haloarenes coupled with vinylic N-methyliminodiacetic acid (MIDA) boronates generate ortho-vinyl-nitroarenes, which undergo a "metal-free" nitrene insertion, resulting in a new pyrrole ring. This novel synthetic approach has a wide substrate tolerance and it is applicable in the preparation of more complex "drug-like" molecules. Interestingly, an ortho-nitro-allylarene derivative furnished a cyclic beta-aminophosphonate motif.

机译：报道了结构上不同的含吡咯的双环体系的两步合成。将邻硝基硝基卤代芳烃与乙烯基N-甲基亚氨基二乙酸（MIDA）硼酸酯偶联，可生成邻乙烯基硝基硝基芳烃，并进行“无金属”的氮烯插入，从而形成新的吡咯环。这种新颖的合成方法具有广泛的底物耐受性，并且可用于制备更复杂的“药物样”分子。有趣的是，邻硝基烯丙基芳烃衍生物提供了环状β-氨基膦酸酯基序。

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来源
《Chemistry: A European journal》 |2015年第20期|共5页
作者
Llona-Minguez Sabin; Desroses Matthieu; Ghassemian Artin; Jacques Sylvain A.; Eriksson Lars; Isacksson Rebecka; Koolmeister Tobias; Stenmark Pal; Scobie Martin; Helleday Thomas;
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正文语种 eng
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aminophosphonate; boronate; cyclization; heterocycles; MIDA; nitrene;

机译：氨基膦酸酯;硼酸酯;环化;杂环;MIDA;硝烯;

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1. Vinylic MIDA Boronates: New Building Blocks for the Synthesis of Aza-Heterocycles [J] . Llona-Minguez Sabin, Desroses Matthieu, Ghassemian Artin, Chemistry: A European journal . 2015,第20期

机译：乙烯基MIDA硼酸酯：合成氮杂杂环的新构件
2. Vinyl MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis [J] . Uno BE, Gillis EP, Burke MD Tetrahedron . 2009,第16期

机译：MIDA硼酸乙烯酯：小分子合成的一种容易获得且用途广泛的构件
3. 1-(Trimethylsilyl)vinyl MIDA Boronate: A Trifunctional C-2 Building Block [J] . Ivon Yevhen M., Voitenko Zoya V., Grygorenko Oleksandr O. Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2018,第9期

机译：1-（三甲基甲硅烷基）乙烯基MINA硼酸盐：三官能的C-2积木
4. SYNTHESIS OF CYCLOSAL-ACTIVATED GLYCOPYRANOSYL PHOSPHATES AND THEIR USE AS KEY BUILDING BLOCKS IN SYNTHESIS [C] . Huchting J., Meier C. International Carbohydrate Symposium . 2013

机译：环塑活性甘吡喃糖基磷酸酯的合成及其用作合成中的关键构建块
5. Copper Promoted Coupling of Vinyl Boronates with Alcohols: A Mild Synthesis of Allyl Vinyl Ethers and Cellular Imaging and Synthesis of the Calcium Sensor Fluoresceindigalactose-Bisaminophenoxyethane-N,N,N',N'-Tetraacetic Acid-Acetoxymethyl Ester [D] . Shade, Ryan Edward 2010

机译：铜促进乙烯基硼酸酯与醇的偶联：烯丙基乙烯基醚的轻度合成和细胞成像以及钙传感器荧光二乳糖-双氨基苯氧基乙烷-N，N，N'，N'-四乙酸-乙酰氧基甲基酯的合成
6. From Synthesis to Function via Iterative Assembly of MIDA Boronate Building Blocks [O] . Junqi Li, Anthony S. Grillo, Martin D. Burke -1

机译：从MIDA硼酸酯构建基块的迭代组装从合成到功能
7. Total synthesis of polyene compounds with N-methyliminodiacetic acid (MIDA) boronate building blocks [O] . 2014

机译：具有N-甲基氨基二乙酸（Mida）硼酸盐构建块的多烯化合物的总合成

Vinylic MIDA Boronates: New Building Blocks for the Synthesis of Aza-Heterocycles

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