10537-08-3Relevant articles and documents
Visible-light-driven Cadogan reaction
Qu, Zhonghua,Wang, Pu,Chen, Xing,Deng, Guo-Jun,Huang, Huawen
, p. 2582 - 2586 (2021/03/09)
Visible-light-driven photochemical Cadogan-type cyclization has been discovered. The organic D-A type photosensitizer 4CzIPN found to be an efficient mediator to transfer energy from photons to the transient intermediate that breaks the barriers of deoxygenation in Cadogan reaction and enables a mild metal-free access to carbazoles and related heterocycles. DFT calculation results indicate mildly endergonic formation of the intermediate complex of nitrobiarenes and PPh3, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.
Synthesis of Carbazoles and Related Heterocycles from Sulfilimines by Intramolecular C?H Aminations
Hashmi, A. Stephen K.,Song, Lina,Tian, Xianhai
supporting information, p. 12342 - 12346 (2020/05/19)
While direct nitrene insertions into C?H bonds have become an important tool for building C?N bonds in modern organic chemistry, the generation of nitrene intermediates always requires transition metals, high temperatures, ultraviolet or laser light. We report a mild synthesis of carbazoles and related building blocks through a visible light-induced intramolecular C?H amination reaction. A striking advantage of this new method is the use of more reactive aryl sulfilimines instead of the corresponding hazardous azides. Different catalysts and divergent light sources were tested. The reaction scope is broad and the product yield is generally high. An efficient gram-scale synthesis of Clausine C demonstrates the applicability and scalability of this new method.
Carbazole compound, and synthesis method and application of compound
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Paragraph 0058-0061, (2018/06/15)
The invention discloses a carbazole compound represented by a formula (2) and a synthesis method of the compound. A high-iodine salt is taken as a reaction raw material, and under the action of an inorganic nitrogen reagent, an additive, a base and a metal catalyst, a reaction is carried out in a solvent under a condition of 80-150 DEG C to obtain various carbazole compounds. According to the method provided by the invention, nitrogen atoms are introduced in a later period, so that the non-compatibility of nitrogen heterocyclic rings to the reaction conditions such as the metal catalyst and the like in an early reaction period is avoided. In addition, two aryl groups in the high-iodine salt are fully utilized, so that the atomic economic efficiency of the method provided by the present invention is fully exhibited. The carbazole compound prepared by the method provided by the invention can be further applied to the synthesis of non-steroidal anti-inflammatory drug carprofen.