Molecules 2012, 17(2), 1177-1190; doi:10.3390/molecules17021177
Article

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

Received: 5 December 2011; in revised form: 15 January 2012 / Accepted: 17 January 2012 / Published: 30 January 2012
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: The Winterfeldt oxidation (NaOH, DMF, air, rt) of substituted 1,2,3,4-tetrahydro-γ-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 N2 of tetrahydro-γ-carbolines and N5-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 N1-Boc-dihydropyrrolo[3,2-b]quinolones.
Keywords: : Winterfeldt oxidation; 1,2,3,4-tetrahydro-γ-carbolines; dihydropyrrolo[3,2-b]-quinolones; pyrrolo[3,2-b]quinolones
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MDPI and ACS Style

Sheng, R.; Zhu, J.; Hu, Y. 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. Molecules 2012, 17, 1177-1190.

AMA Style

Sheng R, Zhu J, Hu Y. 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. Molecules. 2012; 17(2):1177-1190.

Chicago/Turabian Style

Sheng, Rong; Zhu, Jiangwei; Hu, Yongzhou. 2012. "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." Molecules 17, no. 2: 1177-1190.

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