Assembly of a Benzo-Fused Bridged Ketone Scaffold from 1,5,10-Enediynes through One-Pot Ruthenium-Catalyzed Cyclization/Iodine-Mediated Oxidative Ring Expansion

2017 ◽  
Vol 56 (20) ◽  
pp. 5494-5497 ◽  
Author(s):  
Yoshihiko Yamamoto ◽  
Kei-ichiro Nishimura ◽  
Shota Mori ◽  
Masatoshi Shibuya
Keyword(s):  
Ring Expansion ◽  
One Pot ◽  
Oxidative Ring Expansion

Assembly of a Benzo-Fused Bridged Ketone Scaffold from 1,5,10-Enediynes through One-Pot Ruthenium-Catalyzed Cyclization/Iodine-Mediated Oxidative Ring Expansion

2017 ◽  
Vol 129 (20) ◽  
pp. 5586-5589 ◽  
Author(s):  
Yoshihiko Yamamoto ◽  
Kei-ichiro Nishimura ◽  
Shota Mori ◽  
Masatoshi Shibuya
Keyword(s):  
Ring Expansion ◽  
One Pot ◽  
Oxidative Ring Expansion

Copper-catalyzed construction of eight-membered rings via oxidative ring expansion and intermolecular cyclization sequencing of indoles with amidines: efficient synthesis of benzo[1,3,5]triazocin-6(5H)-ones

2017 ◽  
Vol 53 (49) ◽  
pp. 6601-6604 ◽  
Author(s):  
Wen-Bin Cao ◽  
Xue-Qiang Chu ◽  
Yu Zhou ◽  
Ling Yin ◽  
Xiao-Ping Xu ◽  
...  
Keyword(s):  
Nitrogen Heterocycles ◽  
Ring Expansion ◽  
Efficient Synthesis ◽  
One Pot ◽  
Intermolecular Cyclization ◽  
Oxidative Ring Expansion

Novel and efficient synthesis of eight-membered nitrogen heterocycles in one pot by copper-catalyzed oxidative ring expansion and intermolecular cyclization sequencing of indoles with amidines has been described.

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.

ChemInform Abstract: BF3·OEt2-Mediated One Pot Synthesis of 10-Indolyldibenzo[b,f]azepine Derivatives via Tandem Ring Expansion and C-C Bond Formation.

ChemInform ◽  
2015 ◽  
Vol 46 (13) ◽  
pp. no-no
Author(s):  
Trimurtulu Kotipalli ◽  
Donala Janreddy ◽  
Veerababurao Kavala ◽  
Chun-Wei Kuo ◽  
Ting-Shen Kuo ◽  
...  
Keyword(s):  
Bond Formation ◽  
Ring Expansion ◽  
One Pot ◽  
One Pot Synthesis

The oxidative ring expansion of spiro-annulated chroman-4-ones: Syntheses of the rotenoid core and related benzoxanthones

1998 ◽  
Vol 39 (8) ◽  
pp. 881-884 ◽  
Author(s):  
Christopher D. Gabbutt ◽  
John D. Hepworth ◽  
B. Mark Heron ◽  
Jean-Luc Thomas
Keyword(s):  
Ring Expansion ◽  
Oxidative Ring Expansion
Sign in / Sign up

Export Citation Format

Share Document