Literature DB >> 18351767

Synthesis of naphthalenes through three-component coupling of alkynes, Fischer carbene complexes, and benzaldehyde hydrazones via isoindole intermediates.

Shaofeng Duan1, Dilip K Sinha-Mahapatra, James W Herndon.   

Abstract

The synthesis of naphthalene derivatives through three-component coupling of 2-alkynylbenzaldehyde hydrazones with carbene complexes and electron-deficient alkynes has been examined. The reaction involves formation of an isoindole derivative, followed by intramolecular Diels-Alder reaction, followed by nitrene extrusion. The reaction was highly regioselective using unsymmetrical alkynes.

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Year:  2008        PMID: 18351767      PMCID: PMC2427052          DOI: 10.1021/ol800242n

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


  11 in total

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Review 4.  Multicomponent reactions in solid-phase synthesis.

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5.  Activation of the human Ah receptor by aza-polycyclic aromatic hydrocarbons and their halogenated derivatives.

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6.  Generation and trapping of isobenzofuran intermediates formed in the coupling of Fischer carbene complexes and o-alkynylbenzoyl derivatives

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Journal:  Org Lett       Date:  2000-05-04       Impact factor: 6.005

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8.  First-principle predictions of absolute pKa's of organic acids in dimethyl sulfoxide solution.

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Journal:  J Am Chem Soc       Date:  2004-01-28       Impact factor: 15.419

9.  Expedient synthesis and structure-activity relationships of phenanthroindolizidine and phenanthroquinolizidine alkaloids.

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  3 in total

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Authors:  James W Herndon; Bishnu Dhakal
Journal:  ARKIVOC       Date:  2016-06-21       Impact factor: 1.140

2.  Preparation of phenalenes and hydronaphthacenes through tandem alkyne Fischer-carbene complex coupling and inter- or intramolecular Diels-Alder reactions.

Authors:  Rajesh Kumar Patti; Shaofeng Duan; Zhipeng Wang; James W Herndon
Journal:  Tetrahedron Lett       Date:  2011-08-10       Impact factor: 2.415

3.  Synthesis of highly substituted benzene ring systems through three-component coupling of enyne imines, Fischer carbene complexes, and electron-deficient alkynes.

Authors:  Bishnu Dhakal; Lalith S R Gamage; Yanshi Zhang; James W Herndon
Journal:  Tetrahedron Lett       Date:  2017-02-24       Impact factor: 2.415

  3 in total

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