Literature DB >> 30109939

Transformation of N, N-Dimethylaniline N-Oxides into Diverse Tetrahydroquinoline Scaffolds via Formal Povarov Reactions.

Timothy S Bush1, Glenn P A Yap1, William J Chain1.   

Abstract

A one-pot protocol for the assembly of diversely functionalized tetrahydro-, hexahydrofuro-, hexahydropyrano-, and tetrahydrobenzofuroquinolines from N, N-dimethylaniline N-oxides and various electron-rich olefins in a tandem Polonovski-Povarov sequence is reported. Following activation of the N-O bond with Boc2O, an exocyclic iminium ion is unveiled upon exposure to tin(IV) chloride. A formal inverse-electron-demand aza-Diels-Alder cyclization generates the tetrahydroquinoline core of 29 examples in up to 92% yield.

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Year:  2018        PMID： 30109939      PMCID： PMC6779048          DOI： 10.1021/acs.orglett.8b02318

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  24 in total

1.  Asymmetric hydrogenation of aromatic compounds.

Authors:  Frank Glorius
Journal:  Org Biomol Chem       Date:  2005-10-19       Impact factor: 3.876

2.  Multi-component coupling reactions: synthesis of a guanidine containing analog of the hexahydropyrrolo[3,2-c]quinoline alkaloid martinelline.

Authors:  R A Batey; D A Powell
Journal:  Chem Commun (Camb)       Date:  2001-11-21       Impact factor: 6.222

3.  Air-stable and phosphine-free iridium catalysts for highly enantioselective hydrogenation of quinoline derivatives.

Authors:  Zhi-Wei Li; Tian-Li Wang; Yan-Mei He; Zhi-Jian Wang; Qing-Hua Fan; Jie Pan; Li-Jin Xu
Journal:  Org Lett       Date:  2008-10-28       Impact factor: 6.005

4.  Highly enantioselective iridium-catalyzed hydrogenation of heteroaromatic compounds, quinolines.

Authors:  Wen-Bo Wang; Sheng-Mei Lu; Peng-Yu Yang; Xiu-Wen Han; Yong-Gui Zhou
Journal:  J Am Chem Soc       Date:  2003-09-03       Impact factor: 15.419

5.  Michael Additions of Highly Basic Enolates to ortho-Quinone Methides.

Authors:  Robert S Lewis; Christopher J Garza; Ann T Dang; Te Kie A Pedro; William J Chain
Journal:  Org Lett       Date:  2015-04-23       Impact factor: 6.005

6.  Chiral gold phosphate catalyzed tandem hydroamination/asymmetric transfer hydrogenation enables access to chiral tetrahydroquinolines.

Authors:  Yu-Liu Du; Yue Hu; Yi-Fan Zhu; Xi-Feng Tu; Zhi-Yong Han; Liu-Zhu Gong
Journal:  J Org Chem       Date:  2015-04-16       Impact factor: 4.354

7.  Highly enantioselective hydrogenation of quinolines using phosphine-free chiral cationic ruthenium catalysts: scope, mechanism, and origin of enantioselectivity.

Authors:  Tianli Wang; Lian-Gang Zhuo; Zhiwei Li; Fei Chen; Ziyuan Ding; Yanmei He; Qing-Hua Fan; Junfeng Xiang; Zhi-Xiang Yu; Albert S C Chan
Journal:  J Am Chem Soc       Date:  2011-06-06       Impact factor: 15.419

8.  Dihydropyridine-based multicomponent reactions. Efficient entry into new tetrahydroquinoline systems through Lewis acid-catalyzed formal [4 + 2] cycloadditions.

Authors:  Rodolfo Lavilla; M Carmen Bernabeu; Inés Carranco; José Luis Díaz
Journal:  Org Lett       Date:  2003-03-06       Impact factor: 6.005

9.  Palladium-catalyzed asymmetric hydrogenation of 3-phthalimido substituted quinolines.

Authors:  Xian-Feng Cai; Wen-Xue Huang; Zhang-Pei Chen; Yong-Gui Zhou
Journal:  Chem Commun (Camb)       Date:  2014-08-28       Impact factor: 6.222

10.  Synthesis of Halogenated Anilines by Treatment of N, N-Dialkylaniline N-Oxides with Thionyl Halides.

Authors:  Hayley Reed; Tyler R Paul; William J Chain
Journal:  J Org Chem       Date:  2018-08-09       Impact factor: 4.354
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  1 in total

1.  Borane-catalyzed cascade Friedel-Crafts alkylation/[1,5]-hydride transfer/Mannich cyclization to afford tetrahydroquinolines.

Authors:  Bei-Bei Zhang; Shuo Peng; Feiyi Wang; Cuifen Lu; Junqi Nie; Zuxing Chen; Guichun Yang; Chao Ma
Journal:  Chem Sci       Date:  2021-12-20       Impact factor: 9.825
  1 in total

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