Synthetic communications

Solid??Phase Synthesis of N??Aryl??N′??Carboalkoxy Guanidines by the Mitsunobu Reaction of Fmoc??Guanidines

DE Robinson, PP Seth, EA Jefferson

Index: Robinson, Dale E.; Seth, Punit P.; Jefferson, Elizabeth A. Synthetic Communications, 2004 , vol. 34, # 15 p. 2743 - 2749

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Citation Number: 8

Abstract

Abstract A new method for the solid??phase synthesis of N??aryl??N′??carboalkoxy guanidines is described. Aromatic amines were reacted with Fmoc??isothiocyanate to provide Fmoc?? thioureas, which were coupled with Rink amide resin to provide the corresponding resin?? bound Fmoc??guanidines. Subsequent Mitsunobu alkylation with a variety of alcohols delivered N??aryl??N′ carboalkoxy guanidines in good to high purity after resin cleavage.