A cascade Claisen rearrangement/o-quinone methide formation/electrocyclization approach to 2H-chromenes

2017 ◽  
Vol 53 (44) ◽  
pp. 6021-6024 ◽  
Author(s):  
Liyan Song ◽  
Fang Huang ◽  
Liwen Guo ◽  
Ming-An Ouyang ◽  
Rongbiao Tong
Keyword(s):  
Claisen Rearrangement ◽  
Quinone Methide ◽  
New Approach ◽  
Aromatic Claisen Rearrangement

A new approach to 8-substituted 2H-chromenes is developed, featuring a novel cascade aromatic Claisen rearrangement/o-quinone methide formation/6π-electrocyclization.

Total synthesis of (±)-heliannuol C and E via aromatic Claisen rearrangement

2005 ◽  
Vol 46 (14) ◽  
pp. 2457-2460 ◽  
Author(s):  
James R. Vyvyan ◽  
Jennifer M. Oaksmith ◽  
Bevin W. Parks ◽  
Elaine M. Peterson
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Aromatic Claisen Rearrangement

scholarly journals Acceleration of an Aromatic Claisen Rearrangement via a Designed Spiroligozyme Catalyst that Mimics the Ketosteroid Isomerase Catalytic Dyad

2014 ◽  
Vol 136 (10) ◽  
pp. 3817-3827 ◽  
Author(s):  
Matthew F. L. Parker ◽  
Sílvia Osuna ◽  
Guillaume Bollot ◽  
Shivaiah Vaddypally ◽  
Michael J. Zdilla ◽  
...  
Keyword(s):  
Claisen Rearrangement ◽  
Ketosteroid Isomerase ◽  
Aromatic Claisen Rearrangement ◽  
Catalytic Dyad

scholarly journals Thermal aromatic Claisen rearrangement and Strecker reaction of alkyl(allyl)-aryl ethers under green reaction conditions: Efficient and clean preparation of ortho-allyl phenols (naphthols) and alkyl(allyl)oxyarene-based γ-amino nitriles

2017 ◽  
Vol 6 (6) ◽  
pp. 208-214
Author(s):  
Kheila N. Silgado-Gómez ◽  
Vladimir V. Kouznetsov
Keyword(s):  
Claisen Rearrangement ◽  
Potassium Cyanide ◽  
Solid Catalyst ◽  
Chemical Transformations ◽  
Reaction Conditions ◽  
Alkyl Aryl ◽  
Strecker Reaction ◽  
Aryl Ethers ◽  
Short Time ◽  
Aromatic Claisen Rearrangement

Chemical transformations of 13 diverse allyl(alkyl)-aryl ethers, easily prepared using Williamson reaction of different hydroxyarenes and allyl bromide and alkyl (n-butyl, n-octyl) bromides, were studied. Thermal aromatic Claisen rearrangement of allyl-aryl ethers to obtain ortho-allyl phenols (naphthols) employing propylene carbonate as a nontoxic and biodegradable solvent was described for the first time. The use of this green solvent allowed to enhance notably product yields and reduce significantly the reaction time comparing with the use of 1,2-dichlorobenzene, toxic solvent, which is traditionally employed in this type of Claisen rearrangement. Three-component Strecker reaction of selected alkyl(allyl)-aryl ethers with formyl function on aryl fragment, piperidine and potassium cyanide in the presence of sulfuric acid supported on silica gel (SSA, SiO2-O-SO3H) under mild reaction conditions was used in the preparation of new γ-amino nitriles, analogues of alkaloid girgensohnine [2-(4-hydroxyphenyl)-2-(piperidin-1-yl)acetonitrile], a perspective biological model in the search for new insecticidal agrochemicals against Aedes aegypti. The use of SSA, an inexpensive and reusable solid catalyst, allowed to obtain new series of 2-[4-alkyl(allyl)oxyphenyl]-2-(piperidin-1-yl)acetonitriles in short time at room temperature with good yields.

scholarly journals Total Synthesis of (+)-7,11-Helianane and (+)-5-Chloro-7,11-helianane through Stereoselective Aromatic Claisen Rearrangement

2011 ◽  
Vol 2011 (33) ◽  
pp. 6802-6802
Author(s):  
Francesca Quartieri ◽  
Laura Elisabetta Mesiano ◽  
Daniela Borghi ◽  
Viviana Desperati ◽  
Cesare Gennari ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Aromatic Claisen Rearrangement

Synthesis of Furo[2,3-f]isoquinolines by Aromatic Claisen Rearrangement and Subsequent Cyclization

Synthesis ◽  
2007 ◽  
Vol 2007 (2) ◽  
pp. 284-288 ◽  
Author(s):  
Lajos Novák ◽  
Mercedes Törincsi ◽  
Pál Kolonits ◽  
Endre Pálosi
Keyword(s):  
Claisen Rearrangement ◽  
Subsequent Cyclization ◽  
Aromatic Claisen Rearrangement
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