Next Article in Journal
Protective Effect of Salvia miltiorrhiza Extract Against Renal Ischemia-Reperfusion-Induced Injury in Rats
Previous Article in Journal
Primary, Secondary Metabolites, H2O2, Malondialdehyde and Photosynthetic Responses of Orthosiphon stimaneus Benth. to Different Irradiance Levels
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

,  and *
ZJU-ENS Joint Laboratory of Medicinal Chemistry, Zhejiang University, Hangzhou 310058, China
* Author to whom correspondence should be addressed.
Received: 5 December 2011 / Revised: 15 January 2012 / Accepted: 17 January 2012 / Published: 30 January 2012
Download PDF [316 KB, uploaded 18 June 2014]

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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Export to BibTeX |
EndNote


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.

View more citation formats

Related Articles

Article Metrics

Comments

Citing Articles

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert