Ligand-modulated ring-expansion

2019 ◽  
Vol 55 (9) ◽  
pp. 1245-1248
Author(s):  
Veronica Carta ◽  
Miguel A. Soto ◽  
Mark J. MacLachlan
Keyword(s):  
Ring Opening ◽  
Ring Expansion ◽  
Coordination Site ◽  
Ring Expansion Reaction ◽  
Bulky Ligand ◽  
Fourth Coordination

An unstrained metal-containing macrocycle was ring-expanded by a ring-opening metathesis strategy, leading to the formation of a bimetallic dimeric macrocycle. The reaction is driven by coordination of a bulky ligand, 2,6-lutidine, on the fourth coordination site of the palladium center. In the absence of metal, or with a less bulky ligand, the ring-expansion reaction does not proceed.

scholarly journals Recent Advances in the Synthesis of Hydrogenated Azocine-Containing­ Molecules

Synthesis ◽  
2017 ◽  
Vol 49 (17) ◽  
pp. 3801-3834 ◽  
Author(s):  
Anna Listratova ◽  
Leonid Voskressensky
Keyword(s):  
Ring Opening ◽  
Aldol Condensation ◽  
Ring Expansion ◽  
Radical Cyclization ◽  
Primary Amines ◽  
Ring Closing Metathesis ◽  
Recent Advances ◽  
Activated Alkynes ◽  
Ring Expansion Reaction ◽  
Metal Catalyzed

This review covers recent advances in synthesis of azocine-containing systems. The most approaches towards azocines are discussed.1 Introduction2 Ring-Expansion Reaction2.1 Ring-Expansion Reaction of Cyclopentane Containing the 1,4-Diketone Moiety with Primary Amines (from 5 to 8)2.2 Ring-Expansion Reaction of Annulated Tetrahydropyridines under the Action of Activated Alkynes (from 6 to 8)2.3 Reductive Ring-Expansion Reaction of Cyclic Oximes2.4 Other Ring-Expansion Reactions3 Heck Reaction4 Cycloaddition5 Ring-Closing Metathesis (RCM)6 Cyclization6.1 Metal-Catalyzed Cyclization6.2 Radical Cyclization6.3 Friedel–Crafts Cyclization6.4 Other Examples of Cyclizations7 Microwave- and Photo-Assisted Reactions8 Other Methods8.1 Cascade and Tandem Reactions8.2 Aldol Condensation8.3 Thermolysis8.4 Ring Opening8.5 Other Methods9 Conclusion

scholarly journals Synthesis of quinoline-3-carboxylates by a Rh(II)-catalyzed cyclopropanation-ring expansion reaction of indoles with halodiazoacetates

2015 ◽  
Vol 11 ◽  
pp. 1944-1949 ◽  
Author(s):  
Magnus Mortén ◽  
Martin Hennum ◽  
Tore Bonge-Hansen
Keyword(s):  
Ring Opening ◽  
Ring Expansion ◽  
Novel Synthesis ◽  
Ring Expansion Reaction

In this letter, we report a novel synthesis of ethyl quinoline-3-carboxylates from reactions between a series of indoles and halodiazoacetates. The formation of the quinoline structure is probably the result of a cyclopropanation at the 2- and 3-positions of the indole followed by ring-opening of the cyclopropane and elimination of H–X.

Nickel-Catalyzed Reactions of Silacyclobutanes with Aldehydes:  Ring Opening and Ring Expansion Reaction

2006 ◽  
Vol 8 (3) ◽  
pp. 483-485 ◽  
Author(s):  
Koji Hirano ◽  
Hideki Yorimitsu ◽  
Koichiro Oshima
Keyword(s):  
Ring Opening ◽  
Ring Expansion ◽  
Catalyzed Reactions ◽  
Ring Expansion Reaction

scholarly journals Nickel-Catalyzed Reactions of Silacyclobutanes with Aldehydes: Ring Opening and Ring Expansion Reaction.

ChemInform ◽  
2006 ◽  
Vol 37 (25) ◽  
Author(s):  
Koji Hirano ◽  
Hideki Yorimitsu ◽  
Koichiro Oshima
Keyword(s):  
Ring Opening ◽  
Ring Expansion ◽  
Catalyzed Reactions ◽  
Ring Expansion Reaction

scholarly journals Synthesis and Antiproliferative Activity of Phosphorus Substituted 4-Cyanooxazolines, 2-Aminocyanooxazolines, 2-Iminocyanooxazolidines and 2-Aminocyanothiazolines by Rearrangement of Cyanoaziridines

Molecules ◽  
2021 ◽  
Vol 26 (14) ◽  
pp. 4265
Author(s):  
Victor Carramiñana ◽  
Ana M. Ochoa de Ochoa de Retana ◽  
Francisco Palacios ◽  
Jesús M. de los de los Santos
Keyword(s):  
Ring Opening ◽  
Human Lung ◽  
Ring Expansion ◽  
Moderate Activity ◽  
A549 Cell Line ◽  
One Pot ◽  
Acidic Conditions ◽  
Lung Adenocarcinoma A549 ◽  
High Yields

Several phosphorus-substituted N-acylated cyanoaziridines 2 and N-carbamoylated cyanoziridines 5 were prepared in good to high yields. N-Acylated cyanoaziridines 2 were used, after ring expansion, in an efficient synthesis of oxazoline derivative 3a and in a completely regio-controlled reaction in the presence of NaI. Conversely, N-carbamoyl cyanoaziridines 5 reacted with NaI to obtain a regioisomeric mixture of 2-aminocyanooxazolines 7. Mild acidic conditions can be used for the isomerization of N-thiocarbamoyl cyanoaziridine 6a into a 2-aminocyanothiazoline derivative 8a by using BF3·OEt2 as a Lewis acid. Likewise, a one pot reaction of NH-cyanoaziridines 1 with isocyanates obtained 2-iminocyanooxazolidines 9 regioselectively. This synthetic methodology involves the addition of isocyanates to starting cyanoaziridines to obtain N-carbamoyl cyanoaziridines 5, which after the ring opening, reacts with a second equivalent of isocyanate to give the final 2-imino cyanooxazolidines 9. In addition, the cytotoxic effect on the cell lines derived from human lung adenocarcinoma (A549) was also screened. 2-Iminooxazolidines 9 exhibited moderate activity against the A549 cell line in vitro. Furthermore, a selectivity towards cancer cells (A549) over non-malignant cells (MCR-5) was detected.

Ring expansion and ring opening of 3-halooxindoles with N-alkoxycarbonyl-O-tosylhydroxylamines for divergent access to 4-aminoquinolin-2-ones and N-Cbz-N’-arylureas

2021 ◽  
Author(s):  
Wei-Cheng Yuan ◽  
Jian Zuo ◽  
Shu-Pei Yuan ◽  
Jian-Qiang Zhao ◽  
Zhen-Hua Wang ◽  
...  
Keyword(s):  
Ring Opening ◽  
Ring Expansion

The reaction of N-alkoxycarbonyl-O-tosylhydroxylamines with indol-2-ones in situ generated from 3-halooxindoles has been developed for divergently accessing 4-aminoquinolin-2-ones and N-Cbz-N’-arylureas in good to excellent yields.

ChemInform Abstract: Efficient Synthesis of (.+-.)-Horsfiline Through the MgI2-Catalyzed Ring-Expansion Reaction of a Spiro[cyclopropane-1,3′-indol]-2′-one.

ChemInform ◽  
2000 ◽  
Vol 31 (37) ◽  
pp. no-no
Author(s):  
Christian Fischer ◽  
Christiane Meyers ◽  
Erick M. Carreira
Keyword(s):  
Ring Expansion ◽  
Efficient Synthesis ◽  
Ring Expansion Reaction

Unusual Ring-Expansion Reaction of Polyfluorinated Norbornenoxetanes

Synthesis ◽  
2007 ◽  
Vol 2007 (9) ◽  
pp. 1349-1354 ◽  
Author(s):  
Viacheslav Petrov ◽  
Will Marshall
Keyword(s):  
Ring Expansion ◽  
Ring Expansion Reaction

ChemInform Abstract: Synthesis of Macrocyclic Enaminolactams by Ring Expansion Reaction of 2-Oxocyclododecane-1-carbonitrile with Diarylcarbodiimides.

ChemInform ◽  
2010 ◽  
Vol 27 (28) ◽  
pp. no-no
Author(s):  
W. IVANCEV ◽  
V. I. OGNYANOV ◽  
M. HESSE
Keyword(s):  
Ring Expansion ◽  
Ring Expansion Reaction
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