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Orthogonal Synthesis of Isoindole and Isoquinoline Derivatives from Organic Azides

Benjamin Wei-Qiang Hui and Shunsuke Chiba*

*Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore, Email: shunsukentu.edu.sg

B. W.-Q. Hui, S. Chiba, Org. Lett., 2009, 11, 729-732.

DOI: 10.1021/ol802816k (free Supporting Information)


Abstract

α-Azido carbonyl compounds bearing a 2-alkenylaryl moiety at the α-position are promising precursors for synthesis of isoindole and isoquinoline derivatives via 1,3-dipolar cycloaddition of azides onto alkenes and 6π-electrocyclization of N-H imine intermediates, respectively.

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Key Words

Isoindoles, Isoquinolines, 3,4-Dihydroisoquinolines


ID: J54-Y2009-0460