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Literature DB >> 16805565

Allenyl azide cycloaddition chemistry. Synthesis of annelated indoles from 2-(allenyl)phenyl azide substrates.

Ken S Feldman¹, Malliga R Iyer, D Keith Hester.

Abstract

[reaction: see text] Thermolysis of 2-(allenyl)phenyl azides leads to a cascade cyclization sequence furnishing both C(2)-C(3) and N-C(2) cyclopentannelated indoles.

Entities: Chemical

Mesh：

Substances：
Azides
Indoles

Year: 2006 PMID： 16805565 PMCID： PMC2532842 DOI： 10.1021/ol061216u

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

5 in total

1. Diyl Trapping and Electroreductive Cyclization Reactions.

Authors: R. Daniel Little
Journal: Chem Rev Date: 1996-02-01 Impact factor: 60.622

2. Allenyl azide cycloaddition chemistry. synthesis of pyrrolidine-containing bicycles and tricycles via the possible intermediacy of azatrimethylenemethane species.

Authors: Ken S Feldman; Malliga R Iyer
Journal: J Am Chem Soc Date: 2005-04-06 Impact factor: 15.419

3. Alkynyliodonium Salts in Organic Synthesis. Preparation of Annelated Dihydropyrroles by Cascade Addition/Bicyclization of Dienyltosylamide Anions with Phenyl(propynyl)iodonium Triflate.

Authors: Ken S. Feldman; David. A. Mareska
Journal: J Org Chem Date: 1999-07-23 Impact factor: 4.354

4. Synthesis of octahydroquinolines through the Lewis acid catalyzed reaction of vinyl allenes and imines.

Authors: David Regás; María M Afonso; Matías L Rodríguez; J Antonio Palenzuela
Journal: J Org Chem Date: 2003-10-03 Impact factor: 4.354

5. Efficient method for the synthesis of hetarenoindanones based on 3-arylhetarenes and their conversion into hetarenoindenes.

Authors: Igor A Kashulin; Ilya E Nifant'ev
Journal: J Org Chem Date: 2004-08-06 Impact factor: 4.354

5 in total

7 in total

Allenyl azide cycloaddition chemistry. Synthesis of annelated indoles from 2-(allenyl)phenyl azide substrates.

1. Diyl Trapping and Electroreductive Cyclization Reactions.

2. Allenyl azide cycloaddition chemistry. synthesis of pyrrolidine-containing bicycles and tricycles via the possible intermediacy of azatrimethylenemethane species.

3. Alkynyliodonium Salts in Organic Synthesis. Preparation of Annelated Dihydropyrroles by Cascade Addition/Bicyclization of Dienyltosylamide Anions with Phenyl(propynyl)iodonium Triflate.

4. Synthesis of octahydroquinolines through the Lewis acid catalyzed reaction of vinyl allenes and imines.

5. Efficient method for the synthesis of hetarenoindanones based on 3-arylhetarenes and their conversion into hetarenoindenes.

1. Allenyl azide cycloaddition chemistry. 2,3-cyclopentennelated indole synthesis through indolidene intermediates.

2. Allenyl azide cycloaddition chemistry: application to the total synthesis of (±)-meloscine.

3. Cyclization Cascade of Allenyl Azides: Synergy Between Theory and Experiment.

4. Allenyl azide cycloaddition chemistry. photochemical initiation and CuI mediation leads to improved regioselectivity.

5. Synthesis studies on the Melodinus alkaloid meloscine.

6. Nazarov cyclization of 1,4-pentadien-3-ols: preparation of cyclopenta[b]indoles and spiro[indene-1,4'-quinoline]s.

7. Cyclization cascade of allenyl azides: a dual mechanism.