I2-Promoted site-selective C–C bond cleavage of aryl methyl ketones as C1 synthons for constructing 5-acyl-1H-pyrazolo[3, 4-b]pyridines. Issue 16 (8th July 2022)

• Record Type: Journal Article
• Authors: Zhou, You; Wang, Li-Sheng; Lei, Shuang-Gui; Gao, Yun-Xiang; Ma, Jin-Tian; Yu, Zhi-Cheng; Wu, Yan-Dong; Wu, An-Xin
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 16(2022)
• Page Start: 4416
• Page End: 4420
• Publication Date: 2022-07-08
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo00676f
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A novel iodine promoted [1 + 3 + 2] cleavage cyclization reaction for the synthesis of 1 H -pyrazolo[3, 4- b ]pyridines from aryl methyl ketones, 5-aminopyrazoles and enaminones has been established. Abstract : A novel iodine promoted [1 + 3 + 2] cleavage cyclization reaction for the synthesis of 1 H -pyrazolo[3, 4- b ]pyridines from aryl methyl ketones, 5-aminopyrazoles and enaminones has been established. This transition metal-free catalysis method has simple reaction conditions and good substrate compatibility, and has been demonstrated in the transformation of alkyl and natural molecule-derived enaminones. Mechanistic studies showed that two cyclization pathways affording different key intermediates were involved, but affording the same target product after site-selective cleavage of the unstrained C–C bond of the acyl group.