ChemInform Abstract: Ring Opening of Donor-Acceptor Cyclopropanes with the Azide Ion: A Tool for Construction of N-Heterocycles.

ChemInform ◽  
2015 ◽  
Vol 46 (33) ◽  
pp. no-no
Author(s):  
Konstantin L. Ivanov ◽  
Elena V. Villemson ◽  
Ekaterina M. Budynina ◽  
Olga A. Ivanova ◽  
Igor V. Trushkov ◽  
...  
Keyword(s):  
Ring Opening ◽  
Azide Ion ◽  
Donor Acceptor

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

scholarly journals Cover Picture: Ring Opening of Donor-Acceptor Cyclopropanes with the Azide Ion: A Tool for Construction of N-Heterocycles (Chem. Eur. J. 13/2015)

2015 ◽  
Vol 21 (13) ◽  
pp. 4857-4857
Author(s):  
Konstantin L. Ivanov ◽  
Elena V. Villemson ◽  
Ekaterina M. Budynina ◽  
Olga A. Ivanova ◽  
Igor V. Trushkov ◽  
...  
Keyword(s):  
Ring Opening ◽  
Azide Ion ◽  
J 13 ◽  
Donor Acceptor

Ring Opening of Donor-Acceptor Cyclopropanes with the Azide Ion: A Tool for Construction of N-Heterocycles

2015 ◽  
Vol 21 (13) ◽  
pp. 4975-4987 ◽  
Author(s):  
Konstantin L. Ivanov ◽  
Elena V. Villemson ◽  
Ekaterina M. Budynina ◽  
Olga A. Ivanova ◽  
Igor V. Trushkov ◽  
...  
Keyword(s):  
Ring Opening ◽  
Azide Ion ◽  
Donor Acceptor

scholarly journals Ring Opening of Donor-Acceptor Cyclopropanes with the Azide Ion: A Tool for Construction of N-Heterocycles

2015 ◽  
Vol 21 (13) ◽  
pp. 4861-4861
Author(s):  
Konstantin L. Ivanov ◽  
Elena V. Villemson ◽  
Ekaterina M. Budynina ◽  
Olga A. Ivanova ◽  
Igor V. Trushkov ◽  
...  
Keyword(s):  
Ring Opening ◽  
Azide Ion ◽  
Donor Acceptor

One-Pot Synthesis of γ-Azidobutyronitriles and Their Intramolecular Cycloadditions

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3356-3373
Author(s):  
Ekaterina M. Budynina ◽  
Konstantin L. Ivanov ◽  
Hamidulla B. Tukhtaev ◽  
Feruza O. Tukhtaeva ◽  
Stanislav I. Bezzubov ◽  
...  
Keyword(s):  
Ring Opening ◽  
One Pot ◽  
Activation Effect ◽  
Efficient Procedure ◽  
Thermally Activated ◽  
Azide Ion ◽  
Intramolecular Cycloadditions ◽  
Synthetic Utility ◽  
Donor Acceptor ◽  
Nucleophilic Ring Opening

Efficient gram-scale, one-pot approaches to azidocyanobutyrates and their amidated or decarboxylated derivatives have been developed, starting from commercially available aldehydes and cyanoacetates. These techniques combine (1) Knoevenagel condensation, (2) Corey–Chaykovsky cyclopropanation and (3) nucleophilic ring opening of donor-acceptor cyclopropanes with the azide ion, as well as (4) Krapcho decarboxylation or (4′) amidation. The synthetic utility of the resulting γ-azidonitriles was demonstrated by their transformation into tetrazoles via intramolecular (3+2)-cycloaddition. A condition-dependent activation effect of the α-substituent was revealed in that case. Thermally activated azide–nitrile interaction did not differentiate the presence of an α-electron-withdrawing substituent in γ-azidonitriles, whereas the Lewis acid mediated (SnCl4 or TiCl4) reaction proceeded much easier for azidocyanobutyrates. This allowed us to develop an efficient procedure for converting azidocyanobutyrates into the corresponding tetrazoles.

Donor–Acceptor Cyclopropane Ring Opening with 6-Amino-1,3-dimethyluracil and Its Use in Pyrimido[4,5-b]azepines Synthesis

2021 ◽  
Author(s):  
Anna E. Vartanova ◽  
Irina I. Levina ◽  
Victor B. Rybakov ◽  
Olga A. Ivanova ◽  
Igor V. Trushkov
Keyword(s):  
Ring Opening ◽  
Cyclopropane Ring ◽  
Donor Acceptor

A donor–acceptor conjugated block copolymer of poly(arylenevinylene)s by ring-opening metathesis polymerization

2015 ◽  
Vol 51 (44) ◽  
pp. 9113-9116 ◽  
Author(s):  
Shu-Wei Chang ◽  
Masaki Horie
Keyword(s):  
Block Copolymer ◽  
Ring Opening ◽  
Ring Opening Metathesis Polymerization ◽  
Metathesis Polymerization ◽  
Donor Acceptor

A donor–acceptor conjugated block copolymer of poly(arylenevinylene)s has been synthesized by ring-opening metathesis polymerization.

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.

Catalytic Asymmetric Transformations of Racemic Aziridines

Synthesis ◽  
2020 ◽  
Vol 52 (12) ◽  
pp. 1738-1750 ◽  
Author(s):  
Zhuo Chai
Keyword(s):  
Ring Opening ◽  
Kinetic Resolution ◽  
Short Review ◽  
Asymmetric Transformations ◽  
Parallel Kinetic Resolution ◽  
Donor Acceptor ◽  
Molecular Architectures ◽  
Catalytic Asymmetric ◽  
Asymmetric Transformation ◽  
Asymmetric Ring Opening

The catalytic asymmetric ring-opening transformations of aziridines represent an important strategy for the construction of various chiral nitrogen-containing molecular architectures. This short review covers the progress achieved in the catalytic asymmetric transformation of racemic aziridines, focusing on the catalytic strategies employed for each different type of such aziridines.1 Introduction2 Reaction of Racemic 2-Vinylaziridines3 Reaction of Racemic 2-Alkylaziridines3.1 Regiodivergent Parallel Kinetic Resolution3.2 Kinetic Resolution4 Reaction of Racemic 2-(Hetero)arylaziridines4.1 Kinetic Resolution4.2 Enantioconvergent Transformation5 Reaction of Racemic Donor–Acceptor-Type Aziridines6 Conclusion and Outlook

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