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Synlett 2009(7): 1099-1102  
DOI: 10.1055/s-0028-1088116
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Gold(III)-Catalyzed 1,4-Nucleophilic Addition: Facile Approach to Prepare 2-Amino-1,4-naphthalenedione and 6-Amino-5,8-quinolinedione Derivatives

Chunhui Jiang, 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 23 January 2009
Publication Date:
26 March 2009 (online)

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Abstract

An efficient approach is developed to prepare different 2-amino-1,4-naphthalenedione and 6-amino-5,8-quinolinedione derivatives regioselectively by Au(III)-catalyzed 1,4-nucleophilic addition and subsequent oxidation. A wide variety of primary, secondary, and aromatic amines, as well as allylamine and 2-butynyl­amine are well tolerated under the mild conditions to give products in moderate to good yields.

Key words

sodium tetrachloroaurate - 2-amino-1,4-naphthalene­dione - 6-amino-5,8-quinolinedione

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12

General Procedures for the Preparation of 2-Amino-1,4-naphthalenediones (3a-i) and 6-Amino-5,8-quinoline-diones (3j-n)
1,4-Naphthalenedione (1.0 mmol) or 5,8-quinolinedione (1.0 mmol) and NaAuCl4˙2H2O (0.01 mmol) were dissolved in EtOH (2.0 mL) under oxygen atmosphere. Then the amine (1.3 mmol) was added to the above solution by syringe. The formed solution was heated at 80 ˚C or run at r.t. for a certain time (monitored by TLC). After cooling, the mixture was poured into H2O (20 mL), and extracted with CH2Cl2 (3 × 15 mL). The combined organic extract was dried by anhyd MgSO4, and the solvent was removed by distillation. The crude products obtained were purified by flash chromatog-raphy to give 2-amino-1,4-naphthalenediones and 6-amino-5,8-quinolinediones.