title: Reactivity of p-Toluenesulfonylmethyl Isocyanide: Iron-Involved C-H Tosylmethylation of Imidazopyridines in Nontoxic Media.
abstract: A novel iron-involved tosylmethylation of imidazo[1,2-α]pyridines with p-toluenesulfonylmethyl isocyanide in a solvent mixture of H2O and PEG400 under an Ar atmosphere has been developed. This protocol provides a facile synthetic route for the functionalization of the imidazo[1,2-α]pyridine scaffold with broad substrate compatibility, which is less expensive and environmentally friendly. The current methodology could further enable regioselective C-H tosylmethylation of indole at the C3 position. Also, p-toluenesulfonylmethyl isocyanide was utilized as the tosylmethylating reagent for the first time.
authors.affiliation: College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemisry, Zhengzhou University , No. 100 of Science Road, Zhengzhou, Henan 450001, P. R. China.
authors.forename: Shuai
authors.initials: S
authors.lastname: Lu
authors.affiliation: College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemisry, Zhengzhou University , No. 100 of Science Road, Zhengzhou, Henan 450001, P. R. China.
authors.forename: Xinju
authors.initials: X
authors.lastname: Zhu
authors.affiliation: College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemisry, Zhengzhou University , No. 100 of Science Road, Zhengzhou, Henan 450001, P. R. China.
authors.forename: Ke
authors.initials: K
authors.lastname: Li
authors.affiliation: College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemisry, Zhengzhou University , No. 100 of Science Road, Zhengzhou, Henan 450001, P. R. China.
authors.forename: Yu-Jing
authors.initials: YJ
authors.lastname: Guo
authors.affiliation: College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemisry, Zhengzhou University , No. 100 of Science Road, Zhengzhou, Henan 450001, P. R. China.
authors.forename: Meng-Dan
authors.initials: MD
authors.lastname: Wang
authors.affiliation: College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemisry, Zhengzhou University , No. 100 of Science Road, Zhengzhou, Henan 450001, P. R. China.
authors.forename: Xue-Mei
authors.initials: XM
authors.lastname: Zhao
authors.affiliation: College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemisry, Zhengzhou University , No. 100 of Science Road, Zhengzhou, Henan 450001, P. R. China.
authors.forename: Xin-Qi
authors.initials: XQ
authors.lastname: Hao
authors.affiliation: College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemisry, Zhengzhou University , No. 100 of Science Road, Zhengzhou, Henan 450001, P. R. China.
authors.forename: Mao-Ping
authors.initials: MP
authors.lastname: Song
mesh_terms: D066241:Carbon-13 Magnetic Resonance Spectroscopy; D007093:Imidazoles / Q000737:chemistry*; D007501:Iron / Q000737:chemistry*; D013058:Mass Spectrometry; D008745:Methylation; D009570:Nitriles / Q000737:chemistry*; D066244:Proton Magnetic Resonance Spectroscopy; D011725:Pyridines / Q000737:chemistry*; D014105:Tosyl Compounds / Q000737:chemistry*
chemical_list: D007093:Imidazoles; D009570:Nitriles; D011725:Pyridines; D014105:Tosyl Compounds; C000619660:imidazopyridine; C061881:4-toluenesulfonylmethyl isocyanide; D007501:Iron