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Synthesis 2011(21): 3552-3562  
DOI: 10.1055/s-0030-1260221
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Isoindoles via 1,3-Dipolar Cycloaddition of α-Azido Carbonyl Compounds onto Intramolecular Alkenes and Their Conversion into Substituted Aromatic Hydrocarbons

Benny Meng Kiat Tong, Benjamin Wei-Qiang Hui, Sze Hui Chua, Shunsuke Chiba*
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore
Fax: (+65) 6791 1961; e-Mail: shunsuke@ntu.edu.sg;
Further Information

Publication History

Received 19 July 2011
Publication Date:
14 September 2011 (online)

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Abstract

α-Azido carbonyl compounds bearing a 2-alkenylaryl moiety in the α-position are found to be promising precursors in the synthesis of isoindoles via 1,3-dipolar cycloaddition of azides to alkenes. Applications of these isoindoles in the preparation of 1,2,3,4-tetrasubstituted naphthalene and 9,10-disubstituted anthracene derivatives were developed via [4+2]-cycloaddition reactions of isoindoles with dimethyl acetylenedicarboxylate and benzynes, respectively, followed by deaminative aromatization.

Key words

isoindoles - organic azides - 1,3-dipolar cycloaddition - aromatic hydrocarbons - benzynes

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10

The structure of 2a was secured by X-ray crystallographic analysis (see Supporting Information). CCDC-710407 contains the supplementary crystallographic data for compound 2a. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/conts/retrieving.html.

11

The introduction of a carbonyl moiety at C1 in isoindoles is indispensable for this isoindole formation. For an example, the reaction of 2′-vinylbenzyl azide under same reaction conditions gave a complex mixture without the desired isoindoles.