Literature DB >> 15025456

Intramolecular arylation reactions of alkenes: a flexible approach to chromans and tetrahydroquinoline derivatives.

José Barluenga1, Mónica Trincado, Eduardo Rubio, José M González.   

Abstract

A metal-free approach to chroman derivatives by the reaction of different allylphenyl ethers with Ipy2BF4 is described. The access to this frame, by direct cyclization of the starting materials, takes place smoothly. In addition, an unusual and selective sequence that comprises initial rearrangement and further cyclization could be accomplished, with temperature as an excellent element of control. The process can be extended to the synthesis of tetrahydroquinolines when using allylamines. Also, two cascade reactions, leading to relevant oxygen and nitrogen-containing skeletons, have been devised.

Entities:  

Year:  2004        PMID: 15025456     DOI: 10.1021/ja0397299

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  7 in total

1.  Synthesis of naphthalenes and 2-naphthols by the electrophilic cyclization of alkynes.

Authors:  Xiaoxia Zhang; Sampa Sarkar; Richard C Larock
Journal:  J Org Chem       Date:  2006-01-06       Impact factor: 4.354

2.  Selective radical cascade (4+2) annulation with olefins towards the synthesis of chroman derivatives via organo-photoredox catalysis.

Authors:  Zhipeng Guan; Xingxing Zhong; Yayu Ye; Xiangwei Li; Hengjiang Cong; Hong Yi; Heng Zhang; Zhiliang Huang; Aiwen Lei
Journal:  Chem Sci       Date:  2022-04-21       Impact factor: 9.969

3.  Seleniranium ion-triggered reactions: new aspects of Friedel-Crafts and N-detosylative cyclizations.

Authors:  Hwan Jung Lim; T V RajanBabu
Journal:  Org Lett       Date:  2009-07-02       Impact factor: 6.005

4.  Catalytic Alkene Cyclization Reactions for the Stereoselective Synthesis of Complex "Terpenoid-like" Heterocycles.

Authors:  Jared T Moore; Cristian Soldi; James C Fettinger; Jared T Shaw
Journal:  Chem Sci       Date:  2012-10-25       Impact factor: 9.825

5.  Fe(OTf)3-catalysed Friedel-Crafts reaction of benzenoid arenes with α,β-unsaturated carbonyl compounds: easy access to 1,1-diarylalkanes.

Authors:  Aditya Bhattacharya; Pushpendra Mani Shukla; Biswajit Maji
Journal:  R Soc Open Sci       Date:  2017-10-25       Impact factor: 2.963

6.  Oxoammonium salts are catalysing efficient and selective halogenation of olefins, alkynes and aromatics.

Authors:  Weijin Wang; Xinyao Li; Xiaoxue Yang; Lingsheng Ai; Zhiwen Gong; Ning Jiao; Song Song
Journal:  Nat Commun       Date:  2021-06-23       Impact factor: 14.919

7.  Synthesis of Dihydrobenzofuro[3,2-b]chromenes as Potential 3CLpro Inhibitors of SARS-CoV-2: A Molecular Docking and Molecular Dynamics Study.

Authors:  Sudip Gorai; Vivek Junghare; Kshama Kundu; Sowmomita Gharui; Mukesh Kumar; Birija Sankar Patro; Sandip K Nayak; Saugata Hazra; Soumyaditya Mula
Journal:  ChemMedChem       Date:  2022-02-17       Impact factor: 3.540

  7 in total

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