Mild and Efficient Winterfeldt Oxidation of 1,2,3,4-Tetrahydro-γ-carbolines for the Synthesis of Dihydropyrrolo[3,2-b]-quinolones and Pyrrolo[3,2-b]quinolones

作者：Sheng, Rong; Zhu, Jiangwei; Hu, Yongzhou^*

来源：Molecules, 2012, 17(2): 1177-1190.

DOI：10.3390/molecules17021177

• Winterfeldt oxidation
• 1,2,3,4-tetrahydro-gamma-carbolines
• dihydropyrrolo[3,2-b]quinolones
• pyrrolo[3,2-b]quinolones

The Winterfeldt oxidation (NaOH, DMF, air, rt) of substituted 1,2,3,4-tetrahydro-gamma-carbolines has been developed, which provides a convenient and efficient method for the synthesis of the corresponding dihydropyrrolo[3,2-b]quinolones in moderate to excellent yields (38-94%). The generality and substrate scope of this reaction are explored and a possible mechanism is proposed. The results imply that electron-withdrawing groups on N-2 of tetrahydro-gamma-carbolines and N-5-H are necessary. The synthesis of 5 or 7-substituted pyrrolo[3,2-b]quinolones in near quantitative yields was also achieved through deprotection and aromatization of N-1-Boc-dihydropyrrolo[3,2-b]quinolones.

• 出版日期2012-2
• 单位浙江大学