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Synthesis 2010(4): 587-592  
DOI: 10.1055/s-0029-1217138
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Alternative to Pictet-Gams Reaction Triggered by Hendrickson Reagent: Isoquinolines and β-Carbolines from Amides

Mengde Wu, Shaozhong Wang*
State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. of China
Fax: +86(25)83317761; e-Mail: wangsz@nju.edu.cn;
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Publication History

Received 10 September 2009
Publication Date:
20 November 2009 (online)

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Abstract

The Hendrickson reagent derived from triflic anhydride and triphenylphosphine oxide exhibited high oxophilicity and induced the intramolecular cyclization of β-arylethylamides perfectly. Thus, a one-pot protocol to access isoquinoline and β-carboline was developed involving cyclization followed by oxidative aromatization.

Key words

Hendrickson reagent - isoquinoline - β-carboline - β-arylethylamide - manganese(IV) oxide

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