Palladium-Catalyzed Ring-Expansion Reaction of Indoles with Alkynes: From Indoles to Tetrahydroquinoline Derivatives Under Mild Reaction Conditions

2010 ◽  
Vol 49 (24) ◽  
pp. 4036-4041 ◽  
Author(s):  
Zhuangzhi Shi ◽  
Bo Zhang ◽  
Yuxin Cui ◽  
Ning Jiao
Keyword(s):  
Ring Expansion ◽  
Reaction Conditions ◽  
Palladium Catalyzed ◽  
Ring Expansion Reaction

Palladium-Catalyzed Cascade Ring Expansion Reaction of Cyclobutanols that Have a Propargylic Moiety with Nucleophiles.

ChemInform ◽  
2005 ◽  
Vol 36 (11) ◽  
Author(s):  
Masahiro Yoshida ◽  
Yuki Komatsuzaki ◽  
Hideo Nemoto ◽  
Masataka Ihara
Keyword(s):  
Ring Expansion ◽  
Palladium Catalyzed ◽  
Ring Expansion Reaction

A new procedure for the synthesis of water-soluble tri-cationic and -anionic phthalocyanines

2005 ◽  
Vol 09 (09) ◽  
pp. 651-658 ◽  
Author(s):  
Wesley M. Sharman ◽  
Johan E. van Lier
Keyword(s):  
Photodynamic Therapy ◽  
Ring Expansion ◽  
Water Soluble ◽  
Coupling Reactions ◽  
Terminal Alkynes ◽  
Zinc Phthalocyanines ◽  
Palladium Catalyzed ◽  
Metal Insertion ◽  
Ring Expansion Reaction

A series of water-soluble tri-anionic and -cationic substituted phthalocyanines has been synthesized via iodinated boron subphthalocyanines. The latter were opened with differently substituted diiminoisoindolines via the Kobayashi ring expansion reaction followed by metal insertion to exclusively yield the asymmetrically 3:1 substituted iodinated zinc phthalocyanines. These iodinated phthalocyanines readily underwent palladium-catalyzed coupling reactions with terminal alkynes such as 5-hexynoic acid and 10-undecynoic acid to give anionic phthalocyanines, or with 2-ethynylpyridine and 3-ethynylpyridine followed by N -methylation to give cationic phthalocyanines. These novel asymmetrically substituted charged phthalocyanines could have interesting properties as photosensitizers for photodynamic therapy.

A Domino Approach for the Synthesis of 4-Carboxamide Oxazolines from Azirines

Synthesis ◽  
2021 ◽  
Author(s):  
Ali Nikbakht ◽  
Fariba Mohammadi ◽  
Mohammad Sadeq Mousavi ◽  
Kamran Amiri ◽  
Saeed Balalaie ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Ring Expansion ◽  
Target Product ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Bond Forming ◽  
Forming Efficiency ◽  
High Bond ◽  
Ring Expansion Reaction ◽  
Indium Catalyst

A regio- and the diastereoselective ring-expansion reaction of N-acyl aziridine has been described for the synthesis of 4-carboxamide oxazolines using InCl3. A domino Ugi-Joullié/ring expansion reaction of arylphenylazirines, isocyanides, and carboxylic acids led to the target product through N-acylaziridine intermediate in the presence of indium catalyst. The oxazolines were synthesized in moderate to excellent yields with high atom-economy and high bond-forming efficiency under mild reaction conditions.

Palladium-Catalyzed Ring-Expansion Reaction of Cyclobutanols with 2-Haloanilines Leading to Benzazepines and Quinolines

2021 ◽  
Author(s):  
Xiao-Qin Shen ◽  
Xiaowei Yan ◽  
Xing-Guo Zhang
Keyword(s):  
Ring Expansion ◽  
Efficient Synthesis ◽  
Oxidative Rearrangement ◽  
Rearrangement Reaction ◽  
Palladium Catalyzed ◽  
Ring Expansion Reaction ◽  
General Synthesis

A general synthesis of 2-aryl benzazepines has been developed through palladium-catalyzed ring-expansion reaction of cyclobutanols with 2-haloanilines, the further oxidative rearrangement reaction of benzazepines provided an efficient synthesis of 2-acyl...

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