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Synthesis 2010(17): 2949-2956  
DOI: 10.1055/s-0030-1258137
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

gem-Dibromomethylarenes as Aldehyde Surrogates in the Pictet-Spengler Synthesis of Tetrahydroisoquinolines and Isoindoloisoquinolones

Nagaraja Chowdappaa,b, Bailur Sheena Sherigarab, John Kallikat Augustine*a, Kummara Areppaa, Ashis Baran Mandala
a Syngene International Ltd., Biocon Park, Plot Nos. 2 & 3, Bommasandra IV Phase, Jigani Link Road, Bangalore - 560 099, India
Fax: +91(80)28083150; e-Mail: john.kallikat@syngeneintl.com;
b Department of P.G. Studies and Research in Industrial Chemistry, Kuvempu University, Shankaraghatta, Shimoga - 577 451, India
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Publication History

Received 19 April 2010
Publication Date:
30 June 2010 (online)

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Abstract

A new variant of the Pictet-Spengler reaction has been developed using gem-dibromomethylarenes as aldehyde surrogates to afford a variety of tetrahydroisoquinoline and isoindoloisoquinolone ring systems in good yields. These systems comprise important motifs in naturally occurring bioactive substances.

Key words

Pictet-Spengler reaction - gem-dibromomethylarenes - tetrahydroisoquinolines - isoindoloisoquinolinones - microwave irradiation

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