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Literature DB >> 21456588

Three-component synthesis of cyclic enaminones via ketene cyclization.

Abstract

Cyclic six-membered enaminones were synthesized from three components (bromodiazoacetone, primary amine, and alkyne) in high yields via aza-Michael addition, Wolff rearrangement, and nucleophilic ketene cyclization.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2011 PMID： 21456588 PMCID： PMC3099226 DOI： 10.1021/ol200358h

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

9 in total

1. Synthesis of 6- and 7-membered cyclic enaminones: scope and mechanism.

Authors: Micah J Niphakis; Brandon J Turunen; Gunda I Georg
Journal: J Org Chem Date: 2010-10-15 Impact factor: 4.354

2. Amino acid-derived enaminones: a study in ring formation providing valuable asymmetric synthons.

Authors: Brandon J Turunen; Gunda I Georg
Journal: J Am Chem Soc Date: 2006-07-12 Impact factor: 15.419

3. Improved Arndt-Eistert synthesis of alpha-diazoketones requiring minimal diazomethane in the presence of calcium oxide as acid scavenger.

Authors: Vittorio Pace; Guido Verniest; Josep-Vicent Sinisterra; Andrés R Alcántara; Norbert De Kimpe
Journal: J Org Chem Date: 2010-08-20 Impact factor: 4.354

9. Multiple multicomponent macrocyclizations including bifunctional building blocks (MiBs) based on Staudinger and Passerini three-component reactions.

Authors: Fredy Leon; Daniel G Rivera; Ludger A Wessjohann
Journal: J Org Chem Date: 2008-02-02 Impact factor: 4.354

9 in total

1 in total

1. Enantiospecific Synthesis and Biological Investigations of a Nuphar Alkaloid: Proposed Structure of a Castoreum Component.

Authors: Hajime Seki; Gunda I Georg
Journal: European J Org Chem Date: 2014-06-01

1 in total

Three-component synthesis of cyclic enaminones via ketene cyclization.

1. Synthesis of 6- and 7-membered cyclic enaminones: scope and mechanism.

2. Amino acid-derived enaminones: a study in ring formation providing valuable asymmetric synthons.

3. Improved Arndt-Eistert synthesis of alpha-diazoketones requiring minimal diazomethane in the presence of calcium oxide as acid scavenger.

Review 4. Synthetic applications of chiral 2,3-dihydro-4-pyridones.

5. Total syntheses of arylindolizidine alkaloids (+)-ipalbidine and (+)-antofine.

6. Synthesis of tylocrebrine and related phenanthroindolizidines by VOF3-mediated oxidative aryl-alkene coupling.

7. Synthesis of amino acid derived enaminones via Wolff rearrangement using vinylogous amides as carbon nucleophiles.

8. Intramolecular nucleophilic carbonyl trapping of alpha-ketenyl radicals by an amino group.

9. Multiple multicomponent macrocyclizations including bifunctional building blocks (MiBs) based on Staudinger and Passerini three-component reactions.

1. Enantiospecific Synthesis and Biological Investigations of a Nuphar Alkaloid: Proposed Structure of a Castoreum Component.