Arylboronic Acid Catalyzed Direct Condensation of Carboxylic Acids with Ureas.

Unprotected keto- and aldoximes are readily C-allylated with allyl diisopropyl boronate in the presence of arylboronic acid catalysts to yield highly-substituted N-alpha-secondary (2°) and tertiary (3°) hydroxylamines. The method’s synthetic utility is demonstrated with the total synthesis of the trace alkaloid N-methyl-euphococcine. Preliminary experimental and computational mechanistic studies point toward the formation of a boroxine as the active allylating species.

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A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst

Chemical Science ◽

10.1039/d0sc01729a ◽

2020 ◽

Vol 11 (21) ◽

pp. 5572-5576 ◽

Cited By ~ 1

Author(s):

Noboru Hayama ◽

Yusuke Kobayashi ◽

Eriko Sekimoto ◽

Anna Miyazaki ◽

Kiyofumi Inamoto ◽

...

Keyword(s):

Carboxylic Acids ◽

Tertiary Amine ◽

Michael Addition ◽

Arylboronic Acid ◽

Unsaturated Carboxylic Acids

An asymmetric thia-Michael addition of arylthiols to α,β-unsaturated carboxylic acids using a thiourea catalyst that bears arylboronic acid and tertiary amine moieties is reported.

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Preparation of mono- and diacetyl 4,4′-dimethylbiphenyl and their corresponding carboxylic acids: Reactivity, selectivity and isomer distribution studies via Lewis acid catalyzed Friedel-Crafts acetylation/oxidation

Journal of Molecular Catalysis A Chemical ◽

10.1016/j.molcata.2007.03.069 ◽

2007 ◽

Vol 273 (1-2) ◽

pp. 169-176 ◽

Cited By ~ 3

Author(s):

Salam J.J. Titinchi ◽

Fadhil S. Kamounah ◽

Hanna S. Abbo

Keyword(s):

Carboxylic Acids ◽

Lewis Acid ◽

Isomer Distribution ◽

Acid Catalyzed ◽

Distribution Studies

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Isocarbostyrils. II. The Conversion of 2-Methyl-4-acyl-5-nitroisocarbostyrils to 2-Substituted Indole-4-carboxylic Acids

Canadian Journal of Chemistry ◽

10.1139/v71-465 ◽

1971 ◽

Vol 49 (17) ◽

pp. 2797-2802 ◽

Cited By ~ 6

Author(s):

D. E. Horning ◽

G. Lacasse ◽

J. M. Muchowski

Keyword(s):

Sulfuric Acid ◽

Carboxylic Acid ◽

Carboxylic Acids ◽

Alkaline Hydrolysis ◽

Mannich Reaction ◽

Reductive Cyclization ◽

Acid Catalyzed ◽

Acid Anhydrides ◽

Hydrolysis Of ◽

Derivatives Of

The sulfuric acid catalyzed acylation of 2-methyl-5-nitroisocarbostyril with carboxylic acid anhydrides gave the corresponding 4-acylated derivatives 3, which underwent reductive cyclization to 2-substituted derivatives of 4-methyl-1,3,4,5-tetrahydropyrrolo[4.3.2.de]isoquinolin-5-one (4). Alkaline hydrolysis of the six-membered lactam in 4 was accompanied by a retro-Mannich reaction to produce 2-substituted indole-4-carboxylic acids in about 40 % overall yield from 3.

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