Synthesis 2017; 49(06): 1131-1149
DOI: 10.1055/s-0036-1588390
review
© Georg Thieme Verlag Stuttgart · New York

Syntheses of Biologically Active 2-Arylcyclopropylamines

Shin Miyamura
a  Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan
,
Kenichiro Itami
a  Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan
b  Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya 464-8602, Japan
c  JST-ERATO, Itami Molecular Nanocarbon Project, Nagoya University, Chikusa, Nagoya 464-8602, Japan
,
Junichiro Yamaguchi*
d  Department of Applied Chemistry, Waseda University, 3-4-1 Ohkubo, Shinjuku, Tokyo 169-8555, Japan   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 01 September 2016

Accepted after revision: 21 September 2016

Publication Date:
17 January 2017 (online)


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

 
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