Gold-catalysed cyclisation of N-propargylic β-enaminones to form 3-methylene-1-pyrroline derivatives

Kommuru Goutham; N. S. V. M. Rao Mangina; Surisetti Suresh; Pallepogu Raghavaiah; Galla V. Karunakar

doi:10.1039/c3ob42513d

Gold-catalysed cyclisation of N-propargylic β-enaminones to form 3-methylene-1-pyrroline derivatives

Organic & Biomolecular Chemistry ◽

10.1039/c3ob42513d ◽

2014 ◽

Vol 12 (18) ◽

pp. 2869-2873 ◽

Cited By ~ 42

Author(s):

Kommuru Goutham ◽

N. S. V. M. Rao Mangina ◽

Surisetti Suresh ◽

Pallepogu Raghavaiah ◽

Galla V. Karunakar

Keyword(s):

Catalysed Reaction

A gold(i) catalysed reaction between N-propargylic β-enaminones and arynes was developed to access 3-methylene-1-pyrrolines. The title compounds were obtained in 57–78% yields.

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Faculty Opinions recommendation of A surprising observation that oxygen can affect the product enantiopurity of an enzyme-catalysed reaction.

Faculty Opinions – Post-Publication Peer Review of the Biomedical Literature ◽

10.3410/f.717963238.793465251 ◽

2012 ◽

Author(s):

Wolfgang Buckel

Keyword(s):

Catalysed Reaction ◽

Surprising Observation

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662. Quantitative aspects of the base-catalysed reaction of aliphatic aldehydes with iodine. Part II. Acetaldehyde and propionaldehyde

Journal of the Chemical Society (Resumed) ◽

10.1039/jr9620003348 ◽

1962 ◽

pp. 3348 ◽

Cited By ~ 1

Author(s):

C. F. Cullis ◽

P. A. Swain

Keyword(s):

Aliphatic Aldehydes ◽

Catalysed Reaction

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Synthesis of squaric acid derivatives by Lewis acid-catalysed reaction of its dichloride, methyl ester chloride, diethylamide chloride, and ethyl diester with unsaturated organosilanes: new method for C–C bond formation on cyclobutenedione

Journal of the Chemical Society Perkin Transactions 1 ◽

10.1039/p19930000263 ◽

1993 ◽

pp. 263-271 ◽

Cited By ~ 19

Author(s):

Masatomi Ohno ◽

Yoshihiko Yamamoto ◽

Yuhichi Shirasaki ◽

Shoji Eguchi

Keyword(s):

Methyl Ester ◽

Lewis Acid ◽

Bond Formation ◽

New Method ◽

Squaric Acid ◽

Catalysed Reaction

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ChemInform Abstract: NICKEL COMPLEX-CATALYSED REACTION OF PROPYLMAGNESIUM BROMIDE WITH BUTADIENE, A HIGHLY STEREOSELECTIVE SYNTHESIS OF CIS- AND TRANS-(2-VINYLCYCLOPENTYL)METHYLMAGNESIUM BROMIDE

Chemischer Informationsdienst ◽

10.1002/chin.197527329 ◽

1975 ◽

Vol 6 (27) ◽

pp. no-no

Author(s):

H. FELKIN ◽

L. D. KWART ◽

G. SWIERCZEWSKI ◽

J. D. UMPLEBY

Keyword(s):

Nickel Complex ◽

Stereoselective Synthesis ◽

Catalysed Reaction ◽

Cis And Trans

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Kinetics and mechanism of the formation of diaryliodonium salts by sulphuric acid catalysed reaction of substituted phenyl iodosoacetates with aromatic hydrocarbons in acetic acid solution

Journal of the Chemical Society B Physical Organic ◽

10.1039/j29680000093 ◽

1968 ◽

pp. 93 ◽

Cited By ~ 1

Author(s):

J. M. Briody

Keyword(s):

Acetic Acid ◽

Acid Solution ◽

Sulphuric Acid ◽

Aromatic Hydrocarbons ◽

Acetic Acid Solution ◽

Kinetics And Mechanism ◽

Diaryliodonium Salts ◽

Catalysed Reaction

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X-Ray crystal and molecular structure of the p-bromobenzoate derivative of the sesquiterpene (±)-cyclobazzanene obtained in the formic acid-catalysed reaction of (+)-bazzanene

Journal of the Chemical Society Chemical Communications ◽

10.1039/c39770000568 ◽

1977 ◽

pp. 568-569 ◽

Cited By ~ 2

Author(s):

Akihiko Matsuo ◽

Hiroshi Nozaki ◽

Tetsuo Maeda ◽

Mitsuru Nakayama ◽

Yoshihiko Kushi ◽

...

Keyword(s):

Molecular Structure ◽

Formic Acid ◽

Crystal And Molecular Structure ◽

X Ray ◽

Catalysed Reaction

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Synthesis of Water-Soluble 7-O-Carboxymethyl-Genistein

Journal of Chemical Research ◽

10.3184/174751917x14878812592814 ◽

2017 ◽

Vol 41 (3) ◽

pp. 183-185

Author(s):

Zhiling Cao ◽

Qiao Wu ◽

Jing Cheng ◽

Dandan Zhu ◽

Wengqi Teng ◽

...

Keyword(s):

Acetic Acid ◽

Sodium Salt ◽

Water Solubility ◽

Clinical Chemistry ◽

Water Soluble ◽

Aqueous Acetic Acid ◽

Carboxylate Group ◽

Target Compound ◽

Catalysed Reaction

A three-step synthesis from genistein of the water-soluble sodium salt of 7-O-carboxymethyl-genistein is described. Base-catalysed reaction of genistein with t-butyl bromoacetate gave 7-O-(carbo-t-butoxy)methyl-genistein, which was hydrolysed by aqueous acetic acid to 7-O-carboxymethyl-genistein and neutralised (NaHCO3) to give the target compound. The carboxylate group enhanced the water-solubility of genistein more than a thousand-fold and the new derivate will be useful as a candidate compound in pharmacological and clinical chemistry studies of isoflavones.

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