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9-Phenyl-10-methylacridinium: A Highly Efficient and Reusable Organocatalyst for Mild Aromatization of 1,4-Dihydropyridines by Molecular Oxygen

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Xinqiang Fang,^† You-Cheng Liu,*^‡ and Chaozhong Li*^†^‡

Joint Laboratory of Green Synthetic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China, and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China clig@mail.sioc.ac.cn; ycliu@ustc.edu.cn

J. Org. Chem., 2007, 72 (22), pp 8608–8610

DOI: 10.1021/jo701796n

Publication Date (Web): October 5, 2007

Section:

Heterocyclic Compounds (One Hetero Atom)

Abstract

The mild, efficient, and general aerobic aromatization of Hantzsch 1,4-dihydropyridines was realized at room temperature with 5 mol % of 9-phenyl-10-methylacridinium perchlorate as the photocatalyst, which could be easily recovered and reused.

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This article has been cited by 3 ACS Journal articles (3 most recent appear below).

Magnetic Nano-Fe₃O₄-Supported 1-Benzyl-1,4-dihydronicotinamide (BNAH): Synthesis and Application in the Catalytic Reduction of α,β-Epoxy Ketones
Hua-Jian Xu, Xin Wan, Yong-Ya Shen, Song Xu, and Yi-Si Feng
Organic Letters2012 Article ASAP
- Magnetic Nano-Fe₃O₄-Supported 1-Benzyl-1,4-dihydronicotinamide (BNAH): Synthesis and Application in the Catalytic Reduction of α,β-Epoxy Ketones
  Hua-Jian Xu, Xin Wan, Yong-Ya Shen, Song Xu, and Yi-Si Feng
  Organic Letters2012 Article ASAP
  A novel magnetically recoverable organic hydride compound was successfully constructed by using silica-coated magnetic nanoparticles as a support. An as-prepared magnetic organic hydride compound, BNAH (1-benzyl-1,4-dihydronicotinamide), showed efficient ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Photochemical Preparation of Pyrimidin-2(1H)-ones by Rhenium(I) Complexes with Visible Light
Qiang Liu, Ya-Nan Li, Hui-Hui Zhang, Bin Chen, Chen-Ho Tung, and Li-Zhu Wu
The Journal of Organic Chemistry2011 76 (5), 1444-1447
- Photochemical Preparation of Pyrimidin-2(1H)-ones by Rhenium(I) Complexes with Visible Light
  Qiang Liu, Ya-Nan Li, Hui-Hui Zhang, Bin Chen, Chen-Ho Tung, and Li-Zhu Wu
  The Journal of Organic Chemistry2011 76 (5), 1444-1447
  With visible light irradiation (λ > 400 nm) of rhenium(I) complexes (P1−P4), a photochemical conversion from 3,4-dihydropyrimidin-2(1H)-ones to pyrimidin-2(1H)-ones at room temperature has been achieved with good to excellent yields in CH3CN−H2O solution ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Synthesis of Benzo[c]xanthones from 2-Benzylidene-1-tetralones by the Ultraviolet Radiation-Mediated Tandem Reaction
Wen-Zhi Xu, Zhi-Tang Huang and Qi-Yu Zheng
The Journal of Organic Chemistry2008 73 (14), 5606-5608
- Synthesis of Benzo[c]xanthones from 2-Benzylidene-1-tetralones by the Ultraviolet Radiation-Mediated Tandem Reaction
  Wen-Zhi Xu, Zhi-Tang Huang and Qi-Yu Zheng
  The Journal of Organic Chemistry2008 73 (14), 5606-5608
  A facile one-pot method to prepare benzo[c]xanthones from readily accessible benzylidene-1-tetralones by the ultraviolet radiation-mediated tandem reaction is reported. The overall transformation presumably involves cis−trans isomerization, oxa-6π ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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History

Published In Issue October 26, 2007
Received August 15, 2007

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Note

9-Phenyl-10-methylacridinium: A Highly Efficient and Reusable Organocatalyst for Mild Aromatization of 1,4-Dihydropyridines by Molecular Oxygen

Abstract

Citing Articles

Magnetic Nano-Fe₃O₄-Supported 1-Benzyl-1,4-dihydronicotinamide (BNAH): Synthesis and Application in the Catalytic Reduction of α,β-Epoxy Ketones

Magnetic Nano-Fe₃O₄-Supported 1-Benzyl-1,4-dihydronicotinamide (BNAH): Synthesis and Application in the Catalytic Reduction of α,β-Epoxy Ketones

Photochemical Preparation of Pyrimidin-2(1H)-ones by Rhenium(I) Complexes with Visible Light

Photochemical Preparation of Pyrimidin-2(1H)-ones by Rhenium(I) Complexes with Visible Light

Synthesis of Benzo[c]xanthones from 2-Benzylidene-1-tetralones by the Ultraviolet Radiation-Mediated Tandem Reaction