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

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

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 subst...

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Bibliographic Details
Main Authors: Rong Sheng, Jiangwei Zhu, Yongzhou Hu
Format: Article
Language:English
Published: MDPI AG 2012-01-01
Series:Molecules
Subjects:
: Winterfeldt oxidation
1,2,3,4-tetrahydro-γ-carbolines
dihydropyrrolo[3,2-b]-quinolones
pyrrolo[3,2-b]quinolones
Online Access:http://www.mdpi.com/1420-3049/17/2/1177/
id doaj-a313c724a4a840b986bc19d12e041479
record_format Article
spelling doaj-a313c724a4a840b986bc19d12e0414792020-11-25T01:43:03ZengMDPI AGMolecules1420-30492012-01-011721177119010.3390/molecules17021177Mild 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]quinolonesRong ShengJiangwei ZhuYongzhou HuThe 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.http://www.mdpi.com/1420-3049/17/2/1177/: Winterfeldt oxidation1,2,3,4-tetrahydro-γ-carbolinesdihydropyrrolo[3,2-b]-quinolonespyrrolo[3,2-b]quinolones
collection DOAJ
language English
format Article
sources DOAJ
author Rong Sheng
Jiangwei Zhu
Yongzhou Hu
spellingShingle Rong Sheng
Jiangwei Zhu
Yongzhou Hu
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
: Winterfeldt oxidation
1,2,3,4-tetrahydro-γ-carbolines
dihydropyrrolo[3,2-b]-quinolones
pyrrolo[3,2-b]quinolones
author_facet Rong Sheng
Jiangwei Zhu
Yongzhou Hu
author_sort Rong Sheng
title 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
title_short 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_sort 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
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2012-01-01
description 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.
topic : Winterfeldt oxidation
1,2,3,4-tetrahydro-γ-carbolines
dihydropyrrolo[3,2-b]-quinolones
pyrrolo[3,2-b]quinolones
url http://www.mdpi.com/1420-3049/17/2/1177/
work_keys_str_mv AT rongsheng mildandefficientwinterfeldtoxidationof1234tetrahydrogcarbolinesforthesynthesisofdihydropyrrolo32bquinolonesandpyrrolo32bquinolones
AT jiangweizhu mildandefficientwinterfeldtoxidationof1234tetrahydrogcarbolinesforthesynthesisofdihydropyrrolo32bquinolonesandpyrrolo32bquinolones
AT yongzhouhu mildandefficientwinterfeldtoxidationof1234tetrahydrogcarbolinesforthesynthesisofdihydropyrrolo32bquinolonesandpyrrolo32bquinolones
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