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In Situ Formation of Vilsmeier Reagents Mediated by Oxalyl Chloride: a Tool for the Selective Synthesis of N ‐Sulfonylformamidines
Author(s) -
Gazvoda Martin,
Kočevar Marijan,
Polanc Slovenko
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300402
Subject(s) - chemistry , oxalyl chloride , formamides , reagent , hydrazine (antidepressant) , moiety , in situ , hydrate , sulfonamide , chloride , combinatorial chemistry , ethanol , organic chemistry , formamide , chromatography
N ‐Sulfonylformamidines were produced from sulfonamides or N ‐acylated sulfonamides using Vilsmeier reagent obtained in situ from N , N ‐disubstituted formamides and oxalyl chloride. Optically active substrates did not racemize during the process. The efficient and mild cleavage of N ‐sulfonylformamidines can be achieved with hydrazine hydrate in ethanol. The entire procedure constitutes a simple method for protecting, and deprotecting, the sulfonamide moiety.