Literature DB >> 19159326

Sequential Cu(I)/Pd(0)-catalyzed multicomponent coupling and annulation protocol for the synthesis of indenoisoquinolines.

Thiruvellore Thatai Jayanth1, Lei Zhang, Thomas S Johnson, Helena C Malinakova.   

Abstract

Copper-catalyzed coupling of imines, vinylstannanes, or alkynes and o-bromoaroyl chlorides followed by Pd(0)-catalyzed annulations afforded indenoisoquinolines. Protocols requiring minimal purifications were developed, providing new methods for the construction of combinatorial libraries.

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Year:  2009        PMID： 19159326      PMCID： PMC3871195          DOI： 10.1021/ol802755z

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


  19 in total

1.  Copper-catalyzed cross-coupling of imines, acid chlorides, and organostannanes: a multicomponent synthesis of alpha-substituted amides.

Authors:  Daniel A Black; Bruce A Arndtsen
Journal:  J Org Chem       Date:  2005-06-24       Impact factor: 4.354

Review 2.  Multi-component syntheses of heterocycles by transition-metal catalysis.

Authors:  Daniel M D'Souza; Thomas J J Müller
Journal:  Chem Soc Rev       Date:  2007-02-19       Impact factor: 54.564

3.  A novel synthesis of benzo[c]phenanthridine skeleton and biological evaluation of isoquinoline derivatives.

Authors:  W J Cho; M J Park; T Imanishi; B H Chung
Journal:  Chem Pharm Bull (Tokyo)       Date:  1999-06       Impact factor: 1.645

4.  Copper-catalyzed multicomponent cascade process for the synthesis of hexahydro-1H-isoindolones.

Authors:  Lei Zhang; Helena C Malinakova
Journal:  J Org Chem       Date:  2007-01-23       Impact factor: 4.354

5.  Facile and convenient syntheses of 6,11-dihydro-5H-indeno[1,2-c]isoquinolin- 5-ones and 6,11-dihydro-5H-indolo[3,2-c]isoquinolin-5-one.

Authors:  Prakash G Jagtap; Erkan Baloglu; Garry Southan; William Williams; Aloka Roy; Alexander Nivorozhkin; Nelson Landrau; Kevin Desisto; Andrew L Salzman; Csaba Szabó
Journal:  Org Lett       Date:  2005-04-28       Impact factor: 6.005

6.  Dihydroindenoisoquinolines function as prodrugs of indenoisoquinolines.

Authors:  Xiangshu Xiao; Ze-Hong Miao; Smitha Antony; Yves Pommier; Mark Cushman
Journal:  Bioorg Med Chem Lett       Date:  2005-06-02       Impact factor: 2.823

7.  Solution-phase parallel synthesis of hexahydro-1H-isoindolone libraries via tactical combination of Cu-catalyzed three-component coupling and Diels-Alder reactions.

Authors:  Lei Zhang; Gerald H Lushington; Benjamin Neuenswander; John C Hershberger; Helena C Malinakova
Journal:  J Comb Chem       Date:  2008-02-01

Review 8.  Next generation topoisomerase I inhibitors: Rationale and biomarker strategies.

Authors:  Beverly A Teicher
Journal:  Biochem Pharmacol       Date:  2007-10-22       Impact factor: 5.858

9.  Novel indenoisoquinolines NSC 725776 and NSC 724998 produce persistent topoisomerase I cleavage complexes and overcome multidrug resistance.

Authors:  Smitha Antony; Keli K Agama; Ze-Hong Miao; Kazutaka Takagi; Mollie H Wright; Ana I Robles; Lyuba Varticovski; Muthukaman Nagarajan; Andrew Morrell; Mark Cushman; Yves Pommier
Journal:  Cancer Res       Date:  2007-11-01       Impact factor: 12.701

10.  Copper-catalyzed coupling of imines, acid chlorides, and alkynes: a multicomponent route to propargylamides.

Authors:  Daniel A Black; Bruce A Arndtsen
Journal:  Org Lett       Date:  2004-04-01       Impact factor: 6.005
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  3 in total

Review 1.  Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2009.

Authors:  Roland E Dolle; Bertrand Le Bourdonnec; Karin Worm; Guillermo A Morales; Craig J Thomas; Wei Zhang
Journal:  J Comb Chem       Date:  2010-10-05

2.  Application of sequential Cu(I)/Pd(0)-catalysis to solution-phase parallel synthesis of combinatorial libraries of dihydroindeno[1,2-c]isoquinolines.

Authors:  Sarvesh Kumar; Thomas O Painter; Benoy K Pal; Benjamin Neuenswander; Helena C Malinakova
Journal:  ACS Comb Sci       Date:  2011-07-20       Impact factor: 3.784

3.  Reversible C-C bond formation using palladium catalysis.

Authors:  Austin D Marchese; Bijan Mirabi; Colton E Johnson; Mark Lautens
Journal:  Nat Chem       Date:  2022-03-17       Impact factor: 24.274
  3 in total

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