Synthesis and Aromatization of Ethyl Esters of cis-4-(Methanesulfonyl)-cis-5-arylprolines. Unusual Synthesis of 5-Aryl-2-acetylpyrrole

Autor:	V. A. Kalyazin, P. S. Petrov, Nikolay V. Somov
Rok vydání:	2021
Předmět:	Ethanol 010405 organic chemistry Chemistry Aryl Organic Chemistry Aromatization Silver acetate 01 natural sciences Medicinal chemistry Cycloaddition 0104 chemical sciences Adduct Sulfone chemistry.chemical_compound Triethylamine
Zdroj:	Russian Journal of Organic Chemistry. 57:170-179
ISSN:	1608-3393 1070-4280
DOI:	10.1134/s1070428021020068
Popis:	1-Bromovinyl and vinyl methyl sulfones undergo 1,3-dipolar cycloaddition reactions with azomethinylides generated in situ from ethyl N-benzylideneglycinates under the action of silver acetate and triethylamine (toluene, 20°C, 48 h) to form ethyl esters of 4-methanesulfonyl-substituted cis-5-arylprolines. The bromo-substituted adducts convert into the corresponding ethyl 5-aryl-1H-pyrrole-2-carboxylates under heating with an excess of DBU in THF or sodium ethylate in ethanol. Heating of the adducts of vinyl methyl sulfone with sodium ethylate in ethanol in sealed ampules at 90°C leads to mixtures of ethyl 5-aryl-1H-pyrrole-2-carboxylates and 5-aryl-2-acetylpyrroles.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::a20f8a739dfbc89476ff332cdb3b8f95 https://doi.org/10.1134/s1070428021020068 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
Nepřihlášeným uživatelům se plný text nezobrazuje	K zobrazení výsledku je třeba se přihlásit.