Literature DB >> 28781577

Expeditious Synthesis of Isoquinolones and Isocoumarins with a Vinyl Borane as an Acetylene Equivalent.

Momar Toure1, Saul Jaime-Figueroa1, George M Burslem1, Craig M Crews1.   

Abstract

An innovative and simple expeditious synthesis of 3,4-unsubstituted isoquinolones and isocoumarins starting from safe and easy to handle two-carbon acetylene equivalent was developed. The synthetic potential of this new method was further demonstrated in the facile total synthesis of two naturally occurring alkaloids: corydaldine and doryanine.

Entities:  

Keywords:  Suzuki coupling; boronate; isocoumarin; isoquinolone; vinyl ether

Year:  2016        PMID： 28781577      PMCID： PMC5542060          DOI： 10.1002/ejoc.201600575

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  47 in total

1.  Rh-catalyzed oxidative coupling between primary and secondary benzamides and alkynes: synthesis of polycyclic amides.

Authors:  Guoyong Song; Dan Chen; Cheng-Ling Pan; Robert H Crabtree; Xingwei Li
Journal:  J Org Chem       Date:  2010-11-05       Impact factor: 4.354

2.  Ruthenium-catalyzed C-H/N-O bond functionalization: green isoquinolone syntheses in water.

Authors:  Lutz Ackermann; Sabine Fenner
Journal:  Org Lett       Date:  2011-11-11       Impact factor: 6.005

Review 3.  Amaryllidaceae and Sceletium alkaloids.

Authors:  J R Lewis
Journal:  Nat Prod Rep       Date:  1994-06       Impact factor: 13.423

4.  Versatile synthesis of isocoumarins and α-pyrones by ruthenium-catalyzed oxidative C-H/O-H bond cleavages.

Authors:  Lutz Ackermann; Jola Pospech; Karolina Graczyk; Karsten Rauch
Journal:  Org Lett       Date:  2012-01-24       Impact factor: 6.005

5.  Rh(III)-catalyzed C-H activation/cyclization of benzamides and diazo compounds to form isocoumarins and α-pyrones.

Authors:  Xing Guang Li; Min Sun; Kai Liu; Qiao Jin; Pei Nian Liu
Journal:  Chem Commun (Camb)       Date:  2015-02-11       Impact factor: 6.222

6.  Enantioselective template-directed [2+2] photocycloadditions of isoquinolones: scope, mechanism and synthetic applications.

Authors:  Susannah C Coote; Alexander Pöthig; Thorsten Bach
Journal:  Chemistry       Date:  2015-03-17       Impact factor: 5.236

7.  Rh(III)-Catalyzed Oxidative Coupling of Benzoic Acids with Geminal-Substituted Vinyl Acetates: Synthesis of 3-Substituted Isocoumarins.

Authors:  Mingliang Zhang; Hui-Jun Zhang; Tiantian Han; Wenqing Ruan; Ting-Bin Wen
Journal:  J Org Chem       Date:  2014-12-01       Impact factor: 4.354

8.  Synthesis of Isocoumarins and alpha-Pyrones via Palladium-Catalyzed Annulation of Internal Alkynes.

Authors:  Richard C. Larock; Mark J. Doty; Xiaojun Han
Journal:  J Org Chem       Date:  1999-11-26       Impact factor: 4.354

9.  Catalyst Controlled Divergent C4/C8 Site-Selective C-H Arylation of Isoquinolones.

Authors:  Soyoung Lee; Shinmee Mah; Sungwoo Hong
Journal:  Org Lett       Date:  2015-07-28       Impact factor: 6.005

10.  Synthesis of N-alkyl and N-aryl isoquinolones and derivatives via Pd-catalysed C-H activation and cyclization reactions.

Authors:  Nana Zhang; Binyao Li; Hongban Zhong; Jianhui Huang
Journal:  Org Biomol Chem       Date:  2012-10-29       Impact factor: 3.876
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