Tetrahedron Letters

Efficient one-pot synthesis of 1-alkoxy-2-arylaminoimidazolines from N-alkoxy-N-(2-aminoethyl)-2-nitrobenzenesulfonamides and arylisothiocyanates

A Mascaraque, L Nieto, C Dardonville

Index: Mascaraque, Ainhoa; Nieto, Lidia; Dardonville, Christophe Tetrahedron Letters, 2008 , vol. 49, # 31 p. 4571 - 4574

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Citation Number: 9

Abstract

A new synthetic approach towards 1-alkoxy-2-aminoimidazolines that uses N-alkoxy-N-(2- aminoethyl)-2-nitrobenzenesulfonamides as nucleophile reagents for the reaction with isothiocyanates is reported. Hence, the synthesis of 1-alkoxy-2-aminoimidazolines was performed in high yield with a one-pot procedure involving thiourea formation, nosyl group removal and spontaneous cyclization (42–77% overall yield).