Palladium-Catalyzed Ring-Opening Reaction of Methyleneaziridines with Carboxylic Acids:  Synthesis of α-Amidoketones

Byoung Ho Oh; Itaru Nakamura; Yoshinori Yamamoto

doi:10.1021/jo035739g

Palladium-Catalyzed Ring-Opening Reaction of Methyleneaziridines with Carboxylic Acids: Synthesis of α-Amidoketones

The Journal of Organic Chemistry ◽

10.1021/jo035739g ◽

2004 ◽

Vol 69 (8) ◽

pp. 2856-2858 ◽

Cited By ~ 20

Author(s):

Byoung Ho Oh ◽

Itaru Nakamura ◽

Yoshinori Yamamoto

Keyword(s):

Carboxylic Acids ◽

Ring Opening ◽

Ring Opening Reaction ◽

Palladium Catalyzed

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Palladium-Catalyzed Ring-Opening Reaction of Methyleneaziridines with Carboxylic Acids: Synthesis of α-Amidoketones (III).

ChemInform ◽

10.1002/chin.200432095 ◽

2004 ◽

Vol 35 (32) ◽

Author(s):

Byoung Ho Oh ◽

Itaru Nakamura ◽

Yoshinori Yamamoto

Keyword(s):

Carboxylic Acids ◽

Ring Opening ◽

Ring Opening Reaction ◽

Palladium Catalyzed

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Efficient Synthesis of Chiral β-Seleno Amides via Ring-Opening Reaction of 2-Oxazolines and Their Application in the Palladium-Catalyzed Asymmetric Allylic Alkylation

The Journal of Organic Chemistry ◽

10.1021/jo051451a ◽

2005 ◽

Vol 70 (22) ◽

pp. 9021-9024 ◽

Cited By ~ 65

Author(s):

Antonio L. Braga ◽

Fabrício Vargas ◽

Jasquer A. Sehnem ◽

Rodolpho C. Braga

Keyword(s):

Ring Opening ◽

Allylic Alkylation ◽

Efficient Synthesis ◽

Asymmetric Allylic Alkylation ◽

Ring Opening Reaction ◽

Palladium Catalyzed

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ChemInform Abstract: HARD ACID AND SOFT NUCLEOPHILE SYSTEMS. 5. RING-OPENING REACTION OF LACTONES TO Ω-ALKYLTHIO- OR Ω-ARYLTHIO CARBOXYLIC ACIDS WITH ALUMINUM HALIDE AND THIOL

Chemischer Informationsdienst ◽

10.1002/chin.198222121 ◽

1982 ◽

Vol 13 (22) ◽

Author(s):

M. NODE ◽

K. NISHIDE ◽

M. OCHIAI ◽

K. FUJI ◽

E. FUJITA

Keyword(s):

Carboxylic Acids ◽

Ring Opening ◽

Ring Opening Reaction ◽

Aluminum Halide

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Synthesis of Planar Chiral 2-Aryl Aroylferrocenes via Palladium-Catalyzed C–C Bond-Cleavage/Ring-Opening Reaction

Organic Letters ◽

10.1021/acs.orglett.1c02775 ◽

2021 ◽

Author(s):

Zengyin Chao ◽

Na Li ◽

Biqiong Hong ◽

Mingming Ma ◽

Zhenhua Gu

Keyword(s):

Ring Opening ◽

Bond Cleavage ◽

Ring Opening Reaction ◽

Palladium Catalyzed

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Hard acid and soft nucleophile systems. 5. Ring-opening reaction of lactones to .omega.-alkylthio- or .omega.-arylthio carboxylic acids with aluminum halide and thiol

The Journal of Organic Chemistry ◽

10.1021/jo00338a020 ◽

1981 ◽

Vol 46 (25) ◽

pp. 5163-5166 ◽

Cited By ~ 22

Author(s):

Manabu Node ◽

Kiyoharu Nishide ◽

Masahito Ochiai ◽

Kaoru Fuji ◽

Eiichi Fujita

Keyword(s):

Carboxylic Acids ◽

Ring Opening ◽

Ring Opening Reaction ◽

Aluminum Halide

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Enantioselective Palladium-Catalyzed Ring-Opening Reaction of Azabenzonorbornadienes with Methyl 2-Iodobenzoate: An Efficient Access tocis-Dihydrobenzo[c]phenanthridinones

Advanced Synthesis & Catalysis ◽

10.1002/adsc.201300452 ◽

2013 ◽

Vol 355 (14-15) ◽

pp. 2833-2838 ◽

Cited By ~ 15

Author(s):

Kang-Lun Huang ◽

Cui Guo ◽

Li-Jie Cheng ◽

Long-Guan Xie ◽

Qi-Lin Zhou ◽

...

Keyword(s):

Ring Opening ◽

Ring Opening Reaction ◽

Efficient Access ◽

Palladium Catalyzed

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Efficient Synthesis of Chiral β-Seleno Amides via Ring-Opening Reaction of 2-Oxazolines and Their Application in the Palladium-Catalyzed Asymmetric Allylic Alkylation.

ChemInform ◽

10.1002/chin.200611200 ◽

2006 ◽

Vol 37 (11) ◽

Author(s):

Antonio L. Braga ◽

Fabricio Vargas ◽

Jasquer A. Sehnem ◽

Rodolpho C. Braga

Keyword(s):

Ring Opening ◽

Allylic Alkylation ◽

Efficient Synthesis ◽

Asymmetric Allylic Alkylation ◽

Ring Opening Reaction ◽

Palladium Catalyzed

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ChemInform Abstract: Trimethyl Ester of Coenzyme PQQ in Redox Reactions with Transition Metals. An Efficient System for the Palladium-Catalyzed Ring-Opening Reaction of α,β-Epoxysilane.

ChemInform ◽

10.1002/chin.199242119 ◽

2010 ◽

Vol 23 (42) ◽

pp. no-no

Author(s):

T. HIRAO ◽

T. MURAKAMI ◽

M. OHNO ◽

Y. OHSHIRO

Keyword(s):

Transition Metals ◽

Ring Opening ◽

Redox Reactions ◽

Efficient System ◽

Ring Opening Reaction ◽

Palladium Catalyzed

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ChemInform Abstract: Formation of 4-N-Arylamino-1-butanol Derivatives from Aromatic Nitro Compounds via a Novel Palladium-Catalyzed Tetrahydrofuran Ring-Opening Reaction.

ChemInform ◽

10.1002/chin.201302065 ◽

2013 ◽

Vol 44 (2) ◽

pp. no-no

Author(s):

Brian W. Moran ◽

Peter T. M. Kenny

Keyword(s):

Ring Opening ◽

Nitro Compounds ◽

Aromatic Nitro Compounds ◽

Ring Opening Reaction ◽

Palladium Catalyzed ◽

Aromatic Nitro

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Palladium-Catalyzed Synthesis of Polysubstituted Pyrazoles by Ring-Opening Reactions of 2H-Azirines with Hydrazones

Synlett ◽

10.1055/s-0040-1707262 ◽

2020 ◽

Author(s):

Jiaan Shao ◽

Ke Shu ◽

Wenteng Chen ◽

Shuangrong Liu ◽

Huajian Zhu ◽

...

Keyword(s):

Ring Opening ◽

Chemical Conversion ◽

Alternative Route ◽

Ring Opening Reaction ◽

Ring Opening Reactions ◽

Palladium Catalyzed ◽

Plausible Mechanism

AbstractA palladium–catalyzed ring-opening reaction of 2H-azirines with hydrazones has been developed. This protocol provides an alternative route for the construction of various polysubstituted pyrazoles with a wide substrate scope. Moreover, a plausible mechanism is proposed for this reaction, which should further enrich the chemical conversion of 2H-azirines.

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