Ring-opening reactions of donor–acceptor cyclopropanes with cyclic ketals and thiol ketals

2020 ◽  
Vol 18 (33) ◽  
pp. 6492-6496 ◽  
Author(s):  
Dongxin Zhang ◽  
Lei Yin ◽  
Junchao Zhong ◽  
Qihang Cheng ◽  
Hu Cai ◽  
...  
Keyword(s):  
Ring Opening ◽  
Ring Opening Reactions ◽  
Donor Acceptor

Cyclic (thiol) ketals were used as hetero-nucleophiles for the ring opening of donor–acceptor cyclopropanes to afford functionalized diethers.

scholarly journals Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleo­philes

Synthesis ◽  
2017 ◽  
Vol 49 (14) ◽  
pp. 3035-3068 ◽  
Author(s):  
Ekaterina Budynina ◽  
Konstantin Ivanov ◽  
Ivan Sorokin ◽  
Mikhail Melnikov
Keyword(s):  
Ring Opening ◽  
Building Blocks ◽  
Simple Approach ◽  
Secondary Amines ◽  
Primary Amines ◽  
Pyrrole Derivatives ◽  
Heteroaromatic Compounds ◽  
Azide Ion ◽  
Ring Opening Reactions ◽  
Donor Acceptor

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 Introduction2 Ring Opening with Amines3 Ring Opening with Amines Accompanied by Secondary Processes Involving the N-Center3.1 Reactions of Cyclopropane-1,1-diesters with Primary and Secondary Amines3.1.1 Synthesis of γ-Lactams3.1.2 Synthesis of Pyrroloisoxazolidines and -pyrazolidines3.1.3 Synthesis of Piperidines3.1.4 Synthesis of Azetidine and Quinoline Derivatives3.2 Reactions of Ketocyclopropanes with Primary Amines: Synthesis of Pyrrole Derivatives3.3 Reactions of Сyclopropane-1,1-dicarbonitriles with Primary Amines: Synthesis of Pyrrole Derivatives4 Ring Opening with Tertiary Aliphatic Amines5 Ring Opening with Amides6 Ring Opening with Hydrazines7 Ring Opening with N-Heteroaromatic Compounds7.1 Ring Opening with Pyridines7.2 Ring Opening with Indoles7.3 Ring Opening with Di- and Triazoles7.4 Ring Opening with Pyrimidines8 Ring Opening with Nitriles (Ritter Reaction)9 Ring Opening with the Azide Ion10 Summary

Ring-opening reactions of cyclopropanes. Part 8.1 Nitrosation of donor–acceptor cyclopropanes

2005 ◽  
Vol 2005 (10) ◽  
pp. 677-681 ◽  
Author(s):  
Flavio Cermola ◽  
Lucrezia Di Gioia ◽  
Maria Liliana Graziano ◽  
Maria Rosaria Iesce
Keyword(s):  
Ring Opening ◽  
Ring Opening Reactions ◽  
Donor Acceptor

The reaction of 2,2-dialkoxycyclopropane-1-carboxylates 1a–d and monoalkoxycyclopropane 1e with NOCl gives isoxazoline- and/or isoxazole-3-carboxylates by regioselective ring-opening at C1–C2 bond. A mechanistic interpretation suggests the intermediacy of well-stabilised dipolar species.

DBU-promoted ring-opening reactions of multi-substituted donor–acceptor cyclopropanes: access to functionalized chalcones with a quaternary carbon group

2020 ◽  
Vol 18 (45) ◽  
pp. 9210-9215
Author(s):  
Naili Luo ◽  
Jiamin Liu ◽  
Shan Wang ◽  
Cunde Wang
Keyword(s):  
Transition Metal ◽  
Ring Opening ◽  
Metal Catalyst ◽  
Quaternary Carbon ◽  
Transition Metal Catalyst ◽  
Ring Opening Reactions ◽  
Donor Acceptor

A strategy to synthesize highly stereoselective chalcones with alkylcyanoacetate subunits via DBU-promoted ring-opening reactions of multi-substituted D–A cyclopropanes has been developed without the requirement of a transition metal catalyst and extra solvent.

Ring-Opening Reactions of Donor–Acceptor Cyclobutanes with Electron-Rich Arenes, Thiols, and Selenols

2019 ◽  
Vol 21 (16) ◽  
pp. 6315-6319 ◽  
Author(s):  
Alexander Kreft ◽  
Stephanie Ehlers ◽  
Peter G. Jones ◽  
Daniel B. Werz
Keyword(s):  
Ring Opening ◽  
Ring Opening Reactions ◽  
Donor Acceptor

Ring-Opening Reactions of Cyclopropanes. Part 8. Nitrosation of Donor—Acceptor Cyclopropanes.

ChemInform ◽  
2006 ◽  
Vol 37 (8) ◽  
Author(s):  
Flavio Cermola ◽  
Lucrezia Di Gioia ◽  
Maria Liliana Graziano ◽  
Maria Rosaria Iesce
Keyword(s):  
Ring Opening ◽  
Ring Opening Reactions ◽  
Donor Acceptor
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