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Ruthenium (II)-Catalyzed C-H Coupling with Diazo compounds: [4+2] Annulation and Facile Synthesis of Indazolone-Fused Cinnolines

Abstract

A robust, efficient and scalable method for the synthesis of 12H-indazolo[2,1-a]cinnolin-12-ones was developed. Significantly, this reaction was the first Ru(II)-catalyzed [4+2] annulation of diazo compounds via C-H activation and a less developed cationic complex [Ru(p-cymene)(MeCN)3(SbF6)2] was found effective for this transformation. The results of primary mechanistic study suggested that the C-H activation process might follow an electrophilic-type metalation/deprotonation mechanism. This method features secondary amine as directing group, atom/step economy, broad substrate scope, mild reaction condition, good to excellent yield and water and air tolerance.

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Publication details

The article was received on 23 Aug 2018, accepted on 12 Sep 2018 and first published on 13 Sep 2018


Article type: Paper
DOI: 10.1039/C8OB02071J
Citation: Org. Biomol. Chem., 2018, Accepted Manuscript
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    Ruthenium (II)-Catalyzed C-H Coupling with Diazo compounds: [4+2] Annulation and Facile Synthesis of Indazolone-Fused Cinnolines

    L. Su, Z. Yu, P. Ren, Z. Luo, W. Hou and H. Xu, Org. Biomol. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8OB02071J

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