Gold-catalyzed oxidation of terminal alkynes to glyoxals and their reactions with 2-phenylimidazo[1, 2-a]pyridines: one-pot synthesis of 1, 2-diones. Issue 40 (3rd September 2021)

• Record Type: Journal Article
• Authors: Liao, Shengrong; Xu, Huayan; Yang, Bin; Wang, Junfeng; Zhou, Xuefeng; Lin, Xiuping; Liu, Yonghong
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 40(2021)
• Page Start: 8735
• Page End: 8739
• Publication Date: 2021-09-03
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01507a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A one-pot procedure with a tandem reaction sequence of oxidative gold catalysis, nucleophilic addition and oxygenation was employed to synthesize 1, 2-diones from 2-phenylimidazo[1, 2- a ]pyridines and terminal alkynes in good yields. Abstract : A novel one-pot protocol for the convenient and efficient synthesis of (2-phenylimidazo[1, 2- a ]pyridin-3-yl)alkane-1, 2-diones (3 ) in good yields (32–88%) from 2-phenylimidazo[1, 2- a ]pyridines (1 ) and terminal alkynes (2 ) has been established with a wide range of substrate scope. A tandem reaction sequence containing gold-catalyzed double oxidations of terminal alkynes to generate glyoxals, nucleophilic addition of 2-phenylimidazo[1, 2- a ]pyridines to glyoxals to yield α-hydroxyl ketones, and oxygenation of the α-hydroxyl ketones to afford the final products 3 under air atmosphere is involved in this method. Simple operation, mild reaction conditions, and widely available substrates make this strategy more affordable.