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用于合成2-芳基对苯二甲酸酯的硝基烯丙基乙酸酯与稳定硫叶立德的(3 + 3)环合反应

(3 + 3) Annulation of Nitroallylic Acetates with Stabilized Sulfur Ylides for the Synthesis of 2-Aryl Terephthalates.

作者信息

Satham Lakshminarayana, Namboothiri Irishi N N

机构信息

Department of Chemistry , Indian Institute of Technology Bombay , Mumbai 400 076 , India.

出版信息

J Org Chem. 2018 Aug 17;83(16):9471-9477. doi: 10.1021/acs.joc.8b00917. Epub 2018 Jul 16.

DOI:10.1021/acs.joc.8b00917
PMID:29969031
Abstract

A novel (3 + 3) annulation approach has been developed for the synthesis of 2-aryl terephthalates from nitroallylic acetates and stabilized sulfur ylides. The 2-aryl terephthalates, which are also biaryls bearing a terephthalate moiety, are formed through a cascade of reactions such as a γ-selective S2' reaction, γ-selective intramolecular Michael addition, and two eliminations in the presence of CsCO in CHCN at room temperature. The products are formal precursors of farnesyltransferase inhibitors and are also potential monomers in polymer chemistry.

摘要

一种新颖的(3 + 3)环化方法已被开发用于从硝基烯丙基乙酸酯和稳定的硫叶立德合成2-芳基对苯二甲酸酯。2-芳基对苯二甲酸酯,也是带有对苯二甲酸酯部分的联芳基化合物,是通过一系列反应形成的,如γ-选择性S2'反应、γ-选择性分子内迈克尔加成以及在室温下于CHCN中CsCO存在下的两次消除反应。这些产物是法尼基转移酶抑制剂的正式前体,也是高分子化学中的潜在单体。

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