Synthesis of 2,3-diaza-anthraquinones via the bidentate Lewis acid catalysed inverse electron-demand Diels–Alder (IEDDA) reaction

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发布日期 2017-04-05

DOI 10.1039/C7QO00172J

影响因子 5.281

作者

Longcheng Hong, Sebastian Ahles, Marcel A. Strauss, Christian Logemann, Hermann A. Wegner

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摘要

The bidentate bisborane Lewis acid catalysed inverse electron-demand Diels–Alder (IEDDA) reaction of 1,4-naphthoquinones (1,4-NQs) with 1,2,4,5-tetrazine (TZ) has been developed for the synthesis of 2,3-diaza-anthraquinones (2,3-DAAQs). Only due to the coordination of TZ with the bisborane catalyst, the IEDDA reaction of electron-deficient 1,4-NQs is possible. The use of TZ as the nitrogen source provides an efficient strategy to the 2,3-diaza-anthraquinones. The 2,3-DAAQs themselves are suitable dienes for a second bidentate Lewis acid catalysed IEDDA reaction with various dienophiles to afford substituted AQs. AQs have been discussed as privileged structures for applications in medicinal as well as materials science.

期刊推荐

Proceedings of the National Academy of Sciences of the United States of America

Kinetics and Catalysis

Pharmacological Reviews

Journal of Physics and Chemistry of Solids

Journal of Organometallic Chemistry

Science

Journal of Heterocyclic Chemistry

Planta Medica

Science Progress

Journal of Medicinal Chemistry

来源期刊

Organic Chemistry Frontiers

CiteScore: 7.8

自引率: 8.7%

年发文量: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Synthesis of 2,3-diaza-anthraquinones via the bidentate Lewis acid catalysed inverse electron-demand Diels–Alder (IEDDA) reaction

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