Literature DB >> 19226134

Assembly of substituted 3-methyleneisoindolin-1-ones via a CuI/l-proline-catalyzed domino reaction process of 2-bromobenzamides and terminal alkynes.

Li Li1, Miao Wang, Xiaojing Zhang, Yongwen Jiang, Dawei Ma.   

Abstract

CuI/l-proline catalyzed coupling of 2-bromobenzamides and terminal alkynes in i-PrOH (or DMF and DMSO) at 85-110 degrees C and subsequent additive cyclization produces substituted 3-methyleneisoindolin-1-ones. Variation of N-substituents, aromatic ring, and methylene part is possible by using suitable starting materials.

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Year:  2009        PMID： 19226134     DOI： 10.1021/ol9000922

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


  5 in total

1.  Palladium-catalyzed annulation of arynes by o-halobenzamides: synthesis of phenanthridinones.

Authors:  Chun Lu; Anton V Dubrovskiy; Richard C Larock
Journal:  J Org Chem       Date:  2012-09-26       Impact factor: 4.354

2.  A simple and convenient one-pot synthesis of substituted isoindolin-1-ones via lithiation, substitution and cyclization of N'-benzyl-N,N-dimethylureas.

Authors:  Keith Smith; Gamal A El-Hiti; Amany S Hegazy; Benson Kariuki
Journal:  Beilstein J Org Chem       Date:  2011-09-06       Impact factor: 2.883

3.  The photodecarboxylative addition of carboxylates to phthalimides as a key-step in the synthesis of biologically active 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones.

Authors:  Ommid Anamimoghadam; Saira Mumtaz; Anke Nietsch; Gaetano Saya; Cherie A Motti; Jun Wang; Peter C Junk; Ashfaq Mahmood Qureshi; Michael Oelgemöller
Journal:  Beilstein J Org Chem       Date:  2017-12-20       Impact factor: 2.883

4.  Efficient synthesis of a (Z)-3-methyleneisoindolin-1-one library using Cu(OAc)₂•H₂O/DBU under microwave irradiation.

Authors:  Li Zhang; Yongliang Zhang; Xin Wang; Jingkang Shen
Journal:  Molecules       Date:  2013-01-04       Impact factor: 4.411

5.  Base-Promoted Cascade Reactions for the Synthesis of 3,3-Dialkylated Isoindolin-1-ones and 3-Methyleneisoindolin-1-ones.

Authors:  Antonio Macchia; Francesco F Summa; Antonia Di Mola; Consiglia Tedesco; Giovanni Pierri; Armin R Ofial; Guglielmo Monaco; Antonio Massa
Journal:  J Org Chem       Date:  2021-10-06       Impact factor: 4.354
  5 in total

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