Syntheses of Biologically Active 2-Arylcyclopropylamines

Shin Miyamura; Kenichiro Itami; Junichiro Yamaguchi

doi:10.1055/s-0036-1588390

Synthesis, Table of Contents

Synthesis 2017; 49(06): 1131-1149
DOI: 10.1055/s-0036-1588390

review

Syntheses of Biologically Active 2-Arylcyclopropylamines

Authors

Shin Miyamura

^aGraduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan
Kenichiro Itami

^aGraduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan

^bInstitute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya 464-8602, Japan

^cJST-ERATO, Itami Molecular Nanocarbon Project, Nagoya University, Chikusa, Nagoya 464-8602, Japan
Junichiro Yamaguchi*

^dDepartment of Applied Chemistry, Waseda University, 3-4-1 Ohkubo, Shinjuku, Tokyo 169-8555, Japan Email: junyamaguchi@waseda.jp

Abstract

All articles of this category

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

Key words

arylcyclopropylamine - cyclopropanes - biologically active compounds

Full Text

References

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