Acid-Promoted Bicyclization of Diaryl Alkynes: Synthesis of 2H-Indazoles with in Situ Generated Diazonium Salt as Nitrogen Source

Autor:	Sailan Chang, Shanliang Dong, Xinfang Xu, Cheng Zhang, Lihua Qiu
Rok vydání:	2018
Předmět:	Reaction conditions In situ Column chromatography Tandem 010405 organic chemistry Chemistry Organic Chemistry 010402 general chemistry Nitrogen source 01 natural sciences Combinatorial chemistry Salt formation 0104 chemical sciences
Zdroj:	The Journal of Organic Chemistry. 83:9125-9136
ISSN:	1520-6904 0022-3263
Popis:	An unprecedented transition-metal-free tandem bicyclization of diaryl alkynes has been disclosed, which provides a streamlined access to a range of polycyclic 2 H-indazoles in high to excellent yields. The salient features of this reaction include readily available starting materials, good functional group compatibility, mild reaction conditions, no column chromatography, high bond-formation efficiency, and ease in further transformations. Notably, this is the first example for the synthesis of 2 H-indazoles with in situ generated diazonium salt as the nitrogen source, and a mechanistic rationale involving an acid-promoted tandem diazonium salt formation/bicyclization process is discussed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::e9d35c8c7691bbb14cb72d78ebfafa62 https://doi.org/10.1021/acs.joc.8b01199 Zobrazit plný text záznamu