Syntheses of Biologically Active 2-Arylcyclopropylamines

Abstract

The 2-arylcyclopropylamine (ACPA) motif is often seen in biologically active compounds. This review focuses on the synthesis of biologically active ACPAs and categorizes, by reaction type, the synthetic methods used toward such compounds. 1 Introduction 2 Cyclopropanation Using Diazo Compounds 2.1 Styrene 2.2 Cinnamate 2.3 Vinyl Phthalimide 2.4 Vinyl Acetamide 2.5 Oxazolone 2.6 Diketopiperazine 3 Cyclopropanation Using Ylides 3.1 Cinnamate 3.2 Nitrostyrene 3.3 Oxirane 3.4 Nitroacetate 4 Transformation of Cyclopropanes 4.1 Iodocyclopropane 4.2 Aminocyclopropane 5 Miscellaneous Methods 5.1 Kulinkovich Reaction 5.2 Three-Component Reaction 5.3 Intramolecular Nucleophilic Cyclization 5.4 Intramolecular Mitsunobu Reaction 5.5 Rearrangement from Cyclobutanone 6 Summary