Synthesis 2017; 49(14): 3035-3068
DOI: 10.1055/s-0036-1589021
short review
© Georg Thieme Verlag Stuttgart · New York

Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleo­philes

Ekaterina M. Budynina*, Konstantin L. Ivanov, Ivan D. Sorokin, Mikhail Ya. Melnikov
  • Lomonosov Moscow State University, Department of Chemistry, Leninskie gory 1-3, Moscow 119991, Russian Federation   Email: ekatbud@kinet.chem.msu.ru
Further Information

Publication History

Received: 06 February 2017

Accepted after revision: 07 April 2017

Publication Date:
18 May 2017 (eFirst)

Abstract

Ring opening of donor–acceptor cyclopropanes with various N-nucleophiles provides a simple approach to 1,3-functionalized compounds that are useful building blocks in organic synthesis, especially in assembling various N-heterocycles, including natural products. In this review, ring-opening reactions of donor–acceptor cyclopropanes with amines, amides, hydrazines, N-heterocycles, nitriles, and the azide ion are summarized.

1 Introduction

2 Ring Opening with Amines

3 Ring Opening with Amines Accompanied by Secondary Processes Involving the N-Center

3.1 Reactions of Cyclopropane-1,1-diesters with Primary and Secondary Amines

3.1.1 Synthesis of γ-Lactams

3.1.2 Synthesis of Pyrroloisoxazolidines and -pyrazolidines

3.1.3 Synthesis of Piperidines

3.1.4 Synthesis of Azetidine and Quinoline Derivatives

3.2 Reactions of Ketocyclopropanes with Primary Amines: Synthesis of Pyrrole Derivatives

3.3 Reactions of Сyclopropane-1,1-dicarbonitriles with Primary Amines: Synthesis of Pyrrole Derivatives

4 Ring Opening with Tertiary Aliphatic Amines

5 Ring Opening with Amides

6 Ring Opening with Hydrazines

7 Ring Opening with N-Heteroaromatic Compounds

7.1 Ring Opening with Pyridines

7.2 Ring Opening with Indoles

7.3 Ring Opening with Di- and Triazoles

7.4 Ring Opening with Pyrimidines

8 Ring Opening with Nitriles (Ritter Reaction)

9 Ring Opening with the Azide Ion

10 Summary