In Situ Formation of Vilsmeier Reagents Mediated by Oxalyl Chloride: a Tool for the Selective Synthesis of  N ‐Sulfonylformamidines | Zendy

Gazvoda Martin | Zendy; Kočevar Marijan | Zendy; Polanc Slovenko | Zendy

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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.

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