202286-41-7Relevant articles and documents
Novel and convenient routes to substituted pyrroles and imidazoles
Katritzky, Alan R.,Zhu, Lie,Lang, Hengyuan,Denisko, Olga,Wang, Zuoquan
, p. 13271 - 13276 (1995)
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.