Literature DB >> 19534479

Cerium(IV) ammonium nitrate is an excellent, general catalyst for the Friedländer and Friedländer-Borsche quinoline syntheses: very efficient access to the antitumor alkaloid luotonin A.

Vellaisamy Sridharan1, Pascual Ribelles, Ma Teresa Ramos, J Carlos Menéndez.   

Abstract

The use of cerium(IV) ammonium nitrate as a catalyst of the Friedländer reaction allows the synthesis of polysubstituted quinoline derivatives in excellent yields, avoiding the traditional harshly basic or acidic conditions. Unlike most other previously known reagents, CAN allows double condensations and is also an excellent catalyst for the Borsche variation of the Friedländer reaction, which has been applied to the very efficient synthesis of the antitumor alkaloid luotonin A.

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Year:  2009        PMID: 19534479     DOI: 10.1021/jo900965f

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  7 in total

1.  Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with ortho-Aminobenzaldehydes. Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone and Ruteacarpine.

Authors:  Matthew T Richers; Indubhusan Deb; Alena Yu Platonova; Chen Zhang; Daniel Seidel
Journal:  Synthesis (Stuttg)       Date:  2013-10-06       Impact factor: 3.157

2.  2,2'-(2,6-Pyridinedi-yl)diquinoline.

Authors:  Luis Ángel Garza Rodríguez; Sylvain Bernès; Perla Elizondo Martínez; Blanca Nájera Martínez
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-02-20

3.  Design and synthesis of C-aryl angular luotonins via a one-pot aza-Nazarov-Friedlander sequence and their Topo-I inhibition studies along with C-aryl vasicinones and luotonins.

Authors:  Sivappa Rasapalli; Vamshikrishna Reddy Sammeta; Zachary F Murphy; James A Golen; Keli Agama; Yves Pommier; Sergey N Savinov
Journal:  Bioorg Med Chem Lett       Date:  2021-03-30       Impact factor: 2.940

4.  Green approach for synthesis of bioactive Hantzsch 1,4-dihydropyridine derivatives based on thiophene moiety via multicomponent reaction.

Authors:  M G Sharma; D P Rajani; H M Patel
Journal:  R Soc Open Sci       Date:  2017-06-14       Impact factor: 2.963

Review 5.  Recent advances in the studies on luotonins.

Authors:  Jing Lu Liang; Hyo Chang Cha; Yurngdong Jahng
Journal:  Molecules       Date:  2011-06-14       Impact factor: 4.411

6.  Domino Nitro Reduction-Friedländer Heterocyclization for the Preparation of Quinolines.

Authors:  Kwabena Fobi; Richard A Bunce
Journal:  Molecules       Date:  2022-06-27       Impact factor: 4.927

7.  B-ring-aryl substituted luotonin A analogues with a new binding mode to the topoisomerase 1-DNA complex show enhanced cytotoxic activity.

Authors:  Víctor González-Ruiz; Irene Pascua; Tamara Fernández-Marcelo; Pascual Ribelles; Giulia Bianchini; Vellaisamy Sridharan; Pilar Iniesta; M Teresa Ramos; Ana I Olives; M Antonia Martín; J Carlos Menéndez
Journal:  PLoS One       Date:  2014-05-15       Impact factor: 3.240

  7 in total

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