59009-61-9Relevant academic research and scientific papers
IBX-Promoted Oxidative Cyclization of N-Hydroxyalkyl Enamines: A Metal-Free Approach toward 2,3-Disubstituted Pyrroles and Pyridines
Gao, Peng,Chen, Huai-Juan,Bai, Zi-Jing,Zhao, Mi-Na,Yang, Desuo,Wang, Juan,Wang, Ning,Du, Lele,Guan, Zheng-Hui
, p. 7939 - 7951 (2020/07/16)
An iodoxybenzoic acid-mediated selected oxidative cyclization of N-hydroxyalkyl enamines was developed. Through this strategy, a variety of 2,3-disubstituted pyrroles and pyridines were produced in good selectivity involving oxidation of alcohol, followed by condensation of aldehyde and α-C of enamines. Furthermore, this metal-free method has several advantages, including the use of environmentally friendly reagents, broad substrate scope, mild reaction conditions, and high efficiency.
Novel and convenient routes to substituted pyrroles and imidazoles
Katritzky, Alan R.,Zhu, Lie,Lang, Hengyuan,Denisko, Olga,Wang, Zuoquan
, p. 13271 - 13276 (2007/10/02)
S-Methyl N-(benzotriazol-1-ylmethyl)thioimidate 6 is obtained by lithiation of the corresponding N-(benzotriazol-1-ylmethyl)thioamide 5 and subsequent reaction with methyl iodide. Derivative 6 undergoes [2+3] cycloaddition reactions with α,β-unsaturated -esters, -ketones and -nitriles, and vinylpyridines which are followed by elimination of benzotriazole and the thioalkoxy group, to give 2,3,4-trisubstituted pyrroles. Lithiation of 6 followed by reactions with imines gives cyclized 4,5-dihydroimidazoles 14 which upon further treatment with ZnBr2 or direct refluxing in toluene yield the 1,2,5-trisubstituted imidazoles 15 in good yields.
Base-Induced Cycloaddition of N-(Tosylmethyl)imino Compounds to Michael Acceptors. Synthesis of 2,3,4-Trisubstituted Pyrroles
Houwing, Hendrik A.,van Leusen, Albert M.
, p. 1127 - 1132 (2007/10/02)
A series of N-(tosylmethyl)imino compounds has been prepared, and applied to a new, base induced, one operational synthesis of otherwise more difficulty accesible 2,3,4-trisubstituted pyrroles from electron deficient olefins.This regiospec
