Publication:
Synthesis of triazolo- and tetrazolo-tetrahydroisoquinolines and isoquinolines via temperature controlled palladium catalysed allene/azide incorporation/intramolecular 1,3-dipolar cycloaddition cascades

Issued Date

2005-08-29

Resource Type

Article

ISSN

00404039

DOI

10.1016/j.tetlet.2005.06.120

Other identifier(s)

2-s2.0-23044505858

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Tetrahedron Letters. Vol.46, No.35 (2005), 5899-5902

Suggested Citation

Xinjie Gai, Ronald Grigg, Shuleewan Rajviroongit, Saiphon Songarsa, Visuvanathar Sridharan Synthesis of triazolo- and tetrazolo-tetrahydroisoquinolines and isoquinolines via temperature controlled palladium catalysed allene/azide incorporation/intramolecular 1,3-dipolar cycloaddition cascades. Tetrahedron Letters. Vol.46, No.35 (2005), 5899-5902. doi:10.1016/j.tetlet.2005.06.120 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/16300

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Title

Synthesis of triazolo- and tetrazolo-tetrahydroisoquinolines and isoquinolines via temperature controlled palladium catalysed allene/azide incorporation/intramolecular 1,3-dipolar cycloaddition cascades

Author(s)

Xinjie Gai
 Ronald Grigg
 Shuleewan Rajviroongit
 Saiphon Songarsa
 Visuvanathar Sridharan

Other Contributor(s)

University of Leeds
 Mahidol University

Abstract

A novel palladium catalysed three-component process is described involving an allene, an aryl iodide containing an activated alkene and TMSN3. The cascade proceeds via a (π-allyl)palladium species which is intercepted by azide anion followed by stereoselective intramolecular 1,3-dipolar cycloaddition of the organoazide to afford substituted triazolo- and tetrazolo-tetrahydroisoquinolines in good yield. These latter products undergo extrusion of nitrogen to afford isoquinolines at 100°C. © 2005 Elsevier Ltd. All rights reserved.

Keyword(s)

Biochemistry, Genetics and Molecular Biology
 Chemistry
 Pharmacology, Toxicology and Pharmaceutics

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URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/16300

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Scopus 2001-2005