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

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

References and Notes

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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.