Literature DB >> 24788461

An intramolecular cascade cyclization of 2-aryl indoles: efficient methods for the construction of 2,3-functionalized indolines and 3-indolinones.

Arun K Ghosh1, Zhi-Hua Chen.   

Abstract

Efficient intramolecular N/O-nucleophilic cyclization of 2-aryl indoles has been developed to afford the corresponding 2-aza-3-oxaindolines and 3-indolinones in 80-95% yield. The methods provided convenient access to fused imidazo[1,2-c]oxazolidinone, oxazolidine, or tetrahydro-1,3-oxazine cores under mild conditions.

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Year:  2014        PMID: 24788461      PMCID: PMC4088936          DOI: 10.1039/c4ob00511b

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  23 in total

Review 1.  Progress in palladium-based catalytic systems for the sustainable synthesis of annulated heterocycles: a focus on indole backbones.

Authors:  Mélanie Platon; Régine Amardeil; Laurent Djakovitch; Jean-Cyrille Hierso
Journal:  Chem Soc Rev       Date:  2012-03-26       Impact factor: 54.564

2.  Design and synthesis of dual inhibitors of HIV reverse transcriptase and integrase: introducing a diketoacid functionality into delavirdine.

Authors:  Zhengqiang Wang; Robert Vince
Journal:  Bioorg Med Chem       Date:  2008-02-08       Impact factor: 3.641

Review 3.  Update 1 of: Synthesis and functionalization of indoles through palladium-catalyzed reactions.

Authors:  Sandro Cacchi; Giancarlo Fabrizi
Journal:  Chem Rev       Date:  2011-05-05       Impact factor: 60.622

4.  Organocatalyzed enantioselective fluorocyclizations.

Authors:  Oscar Lozano; George Blessley; Teresa Martinez del Campo; Amber L Thompson; Guy T Giuffredi; Michela Bettati; Matthew Walker; Richard Borman; Véronique Gouverneur
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

5.  Palladium-catalyzed enantioselective C-3 allylation of 3-substituted-1H-indoles using trialkylboranes.

Authors:  Barry M Trost; Jean Quancard
Journal:  J Am Chem Soc       Date:  2006-05-17       Impact factor: 15.419

Review 6.  Marine indole alkaloids: potential new drug leads for the control of depression and anxiety.

Authors:  Anna J Kochanowska-Karamyan; Mark T Hamann
Journal:  Chem Rev       Date:  2010-08-11       Impact factor: 60.622

7.  Palladium-catalyzed C3-benzylation of indoles.

Authors:  Ye Zhu; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2011-12-09       Impact factor: 15.419

8.  Inhibition of tubulin polymerization by 5,6-dihydroindolo[2,1-alpha]isoquinoline derivatives.

Authors:  M Goldbrunner; G Loidl; T Polossek; A Mannschreck; E von Angerer
Journal:  J Med Chem       Date:  1997-10-24       Impact factor: 7.446

9.  Enzymatic processing of fumiquinazoline F: a tandem oxidative-acylation strategy for the generation of multicyclic scaffolds in fungal indole alkaloid biosynthesis.

Authors:  Brian D Ames; Xinyu Liu; Christopher T Walsh
Journal:  Biochemistry       Date:  2010-09-08       Impact factor: 3.162

10.  Spiro fused diterpene-indole alkaloids from a creek-bottom-derived Aspergillus terreus.

Authors:  Shengxin Cai; Lin Du; Alexandra L Gerea; Jarrod B King; Jianlan You; Robert H Cichewicz
Journal:  Org Lett       Date:  2013-08-07       Impact factor: 6.005

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