N-[1-(2-Chlorophenyl)-2-{1-methyl-5-nitro-4-[(phenylsulfonyl)methyl]-1H-imidazol-2-yl}ethyl]-4-methylbenzenesulfonamide

Autor:	Romain Paoli-Lombardo, Nicolas Primas, Caroline Castera-Ducros, Inès Jacquet, Pascal Rathelot, Patrice Vanelle
Jazyk:	angličtina
Rok vydání:	2023
Předmět:	5-nitroimidazole N-tosylbenzylimine tetrakis(dimethylamino)ethylene (TDAE) vicarious nucleophilic substitution (VNS) Inorganic chemistry QD146-197
Zdroj:	Molbank, Vol 2023, Iss 2, p M1633 (2023)
Druh dokumentu:	article
ISSN:	1422-8599
DOI:	10.3390/M1633
Popis:	In continuation of our research program to develop original synthetic methods using TDAE methodology on nitroheterocyclic substrates, we were able to generate for the first time a stable carbanion in position 2 of the 5-nitroimidazole scaffold. Starting from a 2-chloromethyl-4-phenylsulfonylmethyl-5-nitroimidazole intermediate, prepared by the vicarious nucleophilic substitution of hydrogen (VNS) reaction, we selectively introduced a N-tosylbenzylimine moiety at position 2 without reducing the sulfone at position 4, leading to the formation of N-[1-(2-chlorophenyl)-2-{1-methyl-5-nitro-4-[(phenylsulfonyl)methyl]-1H-imidazol-2-yl}ethyl]-4-methylbenzenesulfonamide in 47% yield. This new synthetic method using TDAE should allow access to new 2-substituted 5-nitroimidazole derivatives with various electrophiles such as carbonyls and other N-tosylbenzylimines.
Databáze:	Directory of Open Access Journals
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