Organic letters

Efficient synthesis of 3-aminocyclobut-2-en-1-ones: squaramide surrogates as potent VLA-4 antagonists

S Brand, BC de Candole, JA Brown

Index: Brand, Stephen; De Candole, Benjamin C.; Brown, Julien A. Organic Letters, 2003 , vol. 5, # 13 p. 2343 - 2346

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Citation Number: 19

Abstract

A novel series of uniquely functionalized 3-aminocyclobut-2-en-1-ones has been prepared by facile condensation of a variety of cyclobuta-1, 3-diones with a phenylalanine-derived primary amine. These systems subsequently lend themselves to substitution at C-2 by reaction with a variety of electrophilic reagents including N-halosuccinimides, sulfenyl chlorides, and Eschenmoser's salt. Compounds from this novel series are potent ...