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

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

ZJU-ENS Joint Laboratory of Medicinal Chemistry, Zhejiang University, Hangzhou 310058, China
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Received: 5 December 2011 / Revised: 15 January 2012 / Accepted: 17 January 2012 / Published: 30 January 2012
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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 : Winterfeldt oxidation; 1,2,3,4-tetrahydro-γ-carbolines; dihydropyrrolo[3,2-b]-quinolones; pyrrolo[3,2-b]quinolones
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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