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

Chemical Communications ◽

10.1039/d1cc04395a ◽

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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ChemInform Abstract: Efficient Synthesis of (.+-.)-Horsfiline Through the MgI2-Catalyzed Ring-Expansion Reaction of a Spiro[cyclopropane-1,3′-indol]-2′-one.

ChemInform ◽

10.1002/chin.200037216 ◽

2000 ◽

Vol 31 (37) ◽

pp. no-no

Author(s):

Christian Fischer ◽

Christiane Meyers ◽

Erick M. Carreira

Keyword(s):

Ring Expansion ◽

Efficient Synthesis ◽

Ring Expansion Reaction

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

Angewandte Chemie International Edition ◽

10.1002/anie.201001237 ◽

2010 ◽

Vol 49 (24) ◽

pp. 4036-4041 ◽

Cited By ~ 60

Author(s):

Zhuangzhi Shi ◽

Bo Zhang ◽

Yuxin Cui ◽

Ning Jiao

Keyword(s):

Ring Expansion ◽

Reaction Conditions ◽

Palladium Catalyzed ◽

Ring Expansion Reaction

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Palladium-catalyzed ring expansion reaction of 1-alkynylcyclobutanols with aryl iodides: an efficient route to 2-disubstituted methylenecyclopentanones

Tetrahedron Letters ◽

10.1016/s0040-4039(02)02581-9 ◽

2003 ◽

Vol 44 (3) ◽

pp. 595-597 ◽

Cited By ~ 11

Author(s):

Li-Mei Wei ◽

Li-Lan Wei ◽

Wen-Bin Pan ◽

Ming-Jung Wu

Keyword(s):

Ring Expansion ◽

Aryl Iodides ◽

Palladium Catalyzed ◽

Efficient Route ◽

Ring Expansion Reaction

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ChemInform Abstract: A Catalytic Asymmetric Ring-Expansion Reaction of Isatins and α-Alkyl-α-diazoesters. Highly Efficient Synthesis of Functionalized 2-Quinolone Derivatives.

ChemInform ◽

10.1002/chin.201304104 ◽

2013 ◽

Vol 44 (4) ◽

pp. no-no

Author(s):

Wei Li ◽

Xiaohua Liu ◽

Xiaoyu Hao ◽

Yunfei Cai ◽

Lili Lin ◽

...

Keyword(s):

Ring Expansion ◽

Efficient Synthesis ◽

Highly Efficient ◽

Catalytic Asymmetric ◽

Ring Expansion Reaction ◽

Quinolone Derivatives

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

ChemInform ◽

10.1002/chin.200511082 ◽

2005 ◽

Vol 36 (11) ◽

Author(s):

Masahiro Yoshida ◽

Yuki Komatsuzaki ◽

Hideo Nemoto ◽

Masataka Ihara

Keyword(s):

Ring Expansion ◽

Palladium Catalyzed ◽

Ring Expansion Reaction

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Palladium-Catalyzed Ring Expansion Reaction of (Z)-1-(1,3-Butadienyl)cyclobutanols with Aryl Iodides. Stereospecific Synthesis of (Z)-2-(3-Aryl-1-propenyl)cyclopentanones

Organic Letters ◽

10.1021/ol049438k ◽

2004 ◽

Vol 6 (12) ◽

pp. 1979-1982 ◽

Cited By ~ 29

Author(s):

Masahiro Yoshida ◽

Kenji Sugimoto ◽

Masataka Ihara

Keyword(s):

Ring Expansion ◽

Stereospecific Synthesis ◽

Aryl Iodides ◽

Palladium Catalyzed ◽

Ring Expansion Reaction

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

Journal of Porphyrins and Phthalocyanines ◽

10.1142/s1088424605000769 ◽

2005 ◽

Vol 09 (09) ◽

pp. 651-658 ◽

Cited By ~ 18

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.

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