62524-30-5Relevant articles and documents
Efficient Syntheses of 2,5-Dihydropyrroles, Pyrrolidin-3-ones, and Electron-Rich Pyrroles from N-Tosylimines and Lithiated Alkoxyallenes
Okala Amombo, Ghislaine Marlyse,Fl?gel, Oliver,Kord Daoroun Kalai, Scheghajeh,Schoder, Stefan,Warzok, Ulrike,Reissig, Hans-Ulrich
, p. 1965 - 1972 (2017/04/21)
N-Tosylimines and lithiated alkoxyallenes afforded the corresponding allenyl N-tosylamines in good to excellent yields. The 5-endo-trig cyclizations of these intermediates to 2,5-dihydropyrrole derivatives were achieved under strongly basic conditions with potassium tert-butoxide or under milder conditions with either silver(I) or gold(I) catalysis. In general, gold chloride catalyzed reactions occurred with the lowest catalyst loadings and delivered the best yields. With phenyl-substituted 2,5-dihydropyrrole, we investigated typical reactions such as oxidative and reductive transformations. The acid-promoted hydrolysis of the enol ether moieties of three 2,5-dihydropyrroles furnished the corresponding pyrrolidin-3-ones, which were reduced to give 3-hydroxypyrrolidine derivatives in good yields. The aromatization of 2,5-dihydropyrroles to 3-methoxypyrrole derivatives was accomplished by base treatment, which caused the elimination of p-tolyl sulfinate. Electron-rich pyrrole derivatives were synthesized in good yields even on a large scale. All of the experiments illustrate the efficacy and flexibility of the alkoxyallene approach to pyrrole derivatives.
A facile synthesis of 3-alkoxy and 3-amino pyrroles
Breuil-Desvergnes, Valerie,Compain, Philippe,Vatele, Jean-Michel,Gore, Jacques
, p. 8789 - 8792 (2007/10/03)
N-Amino-3-methoxy-3-pyrrolines 2 obtained from the reaction of 1-lithio methoxyallene with arylhydrazones may be converted to either 3-methoxy pyrroles 6 or 3-amino pyrroles 7 by treatment with m-chloroperbenzoic acid or 0.25 M HCl, respectively.
