Literature DB >> 15704906

Synthesis of trisubstituted imidazoles by palladium-catalyzed cyclization of O-pentafluorobenzoylamidoximes: application to amino acid mimetics with a C-terminal imidazole.

Shazia Zaman1, Kitamura Mitsuru, Andrew D Abell.   

Abstract

1-Benzyl-4-methylimidazoles with a range of substituents at the 2-position are prepared from O-pentafluorobenzoylamidoximes on treatment with catalytic amounts of Pd(PPh3)4 and triethylamine. The sequence provides access to optically active amino acid mimetics with a C-terminal imidazole. [structure: see text]

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Year:  2005        PMID: 15704906     DOI: 10.1021/ol047628p

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


  13 in total

Review 1.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

Review 2.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

3.  Synthesis of N-H Bearing Imidazolidinones and Dihydroimidazolones Using Aza-Heck Cyclizations.

Authors:  Feiyang Xu; Scott A Shuler; Donald A Watson
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-19       Impact factor: 15.336

4.  Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction.

Authors:  Scott A Shuler; Guoyin Yin; Sarah B Krause; Caroline M Vesper; Donald A Watson
Journal:  J Am Chem Soc       Date:  2016-10-18       Impact factor: 15.419

5.  Pd-catalyzed Semmler-Wolff reactions for the conversion of substituted cyclohexenone oximes to primary anilines.

Authors:  Wan Pyo Hong; Andrei V Iosub; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2013-09-04       Impact factor: 15.419

6.  A simple, modular synthesis of substituted pyridines.

Authors:  Songbai Liu; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2008-05-09       Impact factor: 15.419

7.  Heck-like Reactions Involving Heteroatomic Electrophiles.

Authors:  Bojan Vulovic; Donald A Watson
Journal:  European J Org Chem       Date:  2017-07-05

Review 8.  Imidazoles as potential anticancer agents.

Authors:  Imran Ali; Mohammad Nadeem Lone; Haasan Y Aboul-Enein
Journal:  Medchemcomm       Date:  2017-04-13       Impact factor: 3.597

9.  Recent developments in the use of aza-Heck cyclizations for the synthesis of chiral N-heterocycles.

Authors:  Nicholas J Race; Ian R Hazelden; Adele Faulkner; John F Bower
Journal:  Chem Sci       Date:  2017-06-20       Impact factor: 9.825

10.  Tandem aza-Heck Suzuki and carbonylation reactions of O-phenyl hydroxamic ethers: complex lactams via carboamination.

Authors:  Run-Duo Gao; Scott A Shuler; Donald A Watson
Journal:  Chem Sci       Date:  2021-05-27       Impact factor: 9.825

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