Cycloaddition. XVIII. Electrophilic addition of chlorosulfonyl isocyanate to ketones. Reaction with aromatic ketones

1975 ◽  
Vol 97 (6) ◽  
pp. 1451-1459 ◽  
Author(s):  
Alfred Hassner ◽  
Jerald K. Rasmussen
Keyword(s):  
Electrophilic Addition ◽  
Aromatic Ketones ◽  
Chlorosulfonyl Isocyanate

(CH)10CO2 interconversions. Electrophilic addition of chlorosulfonyl isocyanate to bullvalene

1970 ◽  
Vol 92 (14) ◽  
pp. 4330-4340 ◽  
Author(s):  
Leo A. Paquette ◽  
Steve. Kirschner ◽  
John R. Malpass
Keyword(s):  
Electrophilic Addition ◽  
Chlorosulfonyl Isocyanate

Stereochemistry of [2+2]Cycloaddition of Chlorosulfonyl Isocyanate to Olefins

2004 ◽  
Vol 8 (6) ◽  
pp. 463-473 ◽  
Author(s):  
Bartlomiej Furman ◽  
Katarzyna Borsuk ◽  
Zbigniew Kaluza ◽  
Robert Lysek ◽  
Marek Chmielewski
Keyword(s):  
Chlorosulfonyl Isocyanate

Selective α,α-Dibromination of Arylethanones with Copper(II) Bromide

2019 ◽  
Vol 16 (9) ◽  
pp. 700-704
Author(s):  
Jitander K. Kapoor ◽  
Loveena Arora ◽  
Om Prakash
Keyword(s):  
Ethyl Acetate ◽  
Heterogeneous System ◽  
Side Chain ◽  
Selective Synthesis ◽  
Aromatic Ketones

Various arylethanones including electron-rich aromatic ketones such as o-hydroxyacetophenone and its p-isomer underwent selective side-chain α,α-dibromination using a heterogeneous system consisting of four molar equivalents of copper(II) bromide in chloroform-ethyl acetate under reflux. This study provides the cleanest method for the selective synthesis of several synthetically useful α,α-dibromoketones which are otherwise difficult to prepare.

A Facile One-pot Synthesis of Substituted Quinolines via Cascade Friedlander Reaction from Isoxazoles with Ammonium Formate-Pd/C and Ketones

2020 ◽  
Vol 17 (3) ◽  
pp. 211-215
Author(s):  
Da Chen ◽  
Xuan Wang ◽  
Runnan Wang ◽  
Yao Zhan ◽  
Xiaohan Peng ◽  
...  
Keyword(s):  
Hydrogen Transfer ◽  
Ammonium Formate ◽  
Aromatic Ketone ◽  
Reaction Conditions ◽  
One Pot ◽  
Diverse Range ◽  
Strong Base ◽  
Aromatic Ketones ◽  
Substituted Quinolines ◽  
New Strategy

The Friedlander reaction is the most commonly used method to synthesis substituted quinolines, the essential intermediates in the medicine industry. A facile one-pot approach for synthesizing substituted quinolines by the reaction of isoxazoles, ammonium formate-Pd/C, concentrated sulfuric acid, methanol and ketones using Friedlander reaction conditions is reported. Procedures for the synthesis of quinoline derivatives were optimized, and the yield was up to 90.4%. The yield of aromatic ketones bearing electron-withdrawing groups was better than the ones with electron-donating substituents. The structures of eight substituted quinolines were characterized by MS, IR, H-NMR and 13CNMR, which were in agreement with the expected structures. The mechanism for the conversion was proposed, which involved the Pd/C catalytic hydrogen transfer reduction of unsaturated five-membered ring of isoxazole to produce ortho-amino aromatic ketones. Then the nucleophilic addition of with carbonyl of the ketones generated Schiff base in situ, which underwent an intermolecular aldol reaction followed by the elimination of H2O to give production of substituted quinolines. This new strategy can be readily applied for the construction of quinolines utilizing a diverse range of ketones and avoids the post-reaction separation of the o-amino aromatic ketone compounds. The conventionally used o-amino aromatic ketone compounds in Friedlander reaction to prepare substituted quinoline are laborious to synthesize and are apt to self-polymerize. While oxazole adopted in this work can be prepared at ease by the condensation of benzoacetonitrile and nitrobenzene derivatives under the catalysis of a strong base. Moreover, the key features of this protocol are readily available starting materials, excellent functional group tolerance, mild reaction conditions, operational simplicity, and feasibility for scaling up.

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