Trifluoroethanol-promoted intramolecular cyclization of 4-(oxiran-2-ylmethoxy)indoles: an easy access to pyrano[2,3-e]indol-3-ols and oxepino[4,3,2-cd]indol-3-ols

2021 ◽  
Author(s):  
Jonali Das ◽  
Sajal Kumar Das
Keyword(s):  
Intramolecular Cyclization ◽  
Ring Opening ◽  
Easy Access ◽  
High Yields ◽  
Intramolecular Ring

Herein, we report that the trifluoroethanol-mediated intramolecular ring opening cyclization of 4-(oxiran-2-ylmethoxy)indoles takes place in diastereoselective and 6-endo fashion to generate pyrano[2,3-e]indol-3-ols in high yields. This regioselective cyclization at indole...

ChemInform Abstract: Au/Ag-Catalyzed Intramolecular Ring-Opening of Vinylidene-Cyclopropanes (VDCPs): An Easy Access to Functional Tetrahydropyrans.

ChemInform ◽  
2010 ◽  
Vol 41 (29) ◽  
pp. no-no
Author(s):  
Wei Li ◽  
Wei Yuan ◽  
Surech Pindi ◽  
Min Shi ◽  
Guigen Li
Keyword(s):  
Ring Opening ◽  
Easy Access ◽  
Intramolecular Ring

Au/Ag-Catalyzed Intramolecular Ring-Opening of Vinylidene-cyclopropanes (VDCPs): An Easy Access to Functional Tetrahydropyrans

2010 ◽  
Vol 12 (5) ◽  
pp. 920-923 ◽  
Author(s):  
Wei Li ◽  
Wei Yuan ◽  
Surech Pindi ◽  
Min Shi ◽  
Guigen Li
Keyword(s):  
Ring Opening ◽  
Easy Access ◽  
Intramolecular Ring

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.

Cu-Catalyzed Ring Opening Reaction of 2H-Azirines with Terminal Alkynes: An Easy Access to 3-Alkynylated Pyrroles

2014 ◽  
Vol 16 (18) ◽  
pp. 4806-4809 ◽  
Author(s):  
Tengfei Li ◽  
Xiaoyi Xin ◽  
Chunxiang Wang ◽  
Dongping Wang ◽  
Fan Wu ◽  
...  
Keyword(s):  
Ring Opening ◽  
Easy Access ◽  
Terminal Alkynes ◽  
Ring Opening Reaction

Intramolecular Ring-Opening Decomposition of Aryl Azetidines

2021 ◽  
Vol 12 (10) ◽  
pp. 1585-1588
Author(s):  
Guoyun Bai ◽  
Thomas N. O’Connell ◽  
Michael A. Brodney ◽  
Christopher R. Butler ◽  
Lara C. Czabaniuk ◽  
...  
Keyword(s):  
Ring Opening ◽  
Intramolecular Ring

Phenolate-induced intramolecular ring-opening cyclization of N-tosylaziridines: access to functionalized benzoxacycles

2018 ◽  
Vol 16 (32) ◽  
pp. 5846-5858 ◽  
Author(s):  
Runjun Devi ◽  
Jonali Das ◽  
Bipul Sarma ◽  
Sajal Kumar Das
Keyword(s):  
Ring Opening ◽  
First Time ◽  
Intramolecular Ring

Phenolate-induced, diastereo- and regioselective intramolecular exo-tet ring-opening cyclization of N-tosylaziridines has been achieved for the first time.

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