Literature DB >> 26797715

Highly efficient synthesis of quinoxaline derivatives from 1,2-benzenediamine and α-aminoxylated 1,3-dicarbonyl compounds.

Jianwei Yan1,2, Yanhong Xu3, Fangfang Zhuang3, Jie Tian3, Guisheng Zhang4.   

Abstract

Simple and efficient synthetic procedures for the preparation of quinoxaline, pyrazine, pyridopyrazine, and benzoxazin-2-one derivatives were developed. The one-pot cascade process involves the acidic elimination of α-aminoxylated dicarbonyl compounds to generate 1,2,3-tricarbonyl compounds and subsequent condensation with 1,4-N,N or -N,O dinucleophiles to afford quinoxaline, pyrazine, pyridopyrazine, and benzoxazin-2-one scaffolds. All the proposed processes do not need extra catalysts, dry solvents, or harsh reaction conditions.

Entities:  

Keywords:  -Aminoxylated dicarbonyl compounds; Benzoxazin-2-one; Pyrazine; Pyridopyrazine; Quinoxaline

Mesh:

Substances:

Year:  2016        PMID: 26797715     DOI: 10.1007/s11030-016-9657-z

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  24 in total

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Journal:  Bioorg Med Chem Lett       Date:  2004-01-19       Impact factor: 2.823

2.  Laterally-extended porphyrin systems incorporating a switchable unit.

Authors:  Maxwell J Crossley; Lesley A Johnston
Journal:  Chem Commun (Camb)       Date:  2002-05-21       Impact factor: 6.222

3.  Antineoplastic agents. 536. New sources of naturally occurring cancer cell growth inhibitors from marine organisms, terrestrial plants, and microorganisms(1a,).

Authors:  George R Pettit; Fiona Hogan; Jun-Ping Xu; Rui Tan; Toshihiko Nogawa; Zbigniew Cichacz; Robin K Pettit; Jiang Du; Qing-Hua Ye; Gordon M Cragg; Cherry L Herald; Michael S Hoard; Animesh Goswami; Justin Searcy; Larry Tackett; Dennis L Doubek; Lee Williams; John N A Hooper; Jean M Schmidt; Jean-Charles Chapuis; Denise N Tackett; Felicia Craciunescu
Journal:  J Nat Prod       Date:  2008-03-08       Impact factor: 4.050

4.  Straightforward access to pyrazines, piperazinones, and quinoxalines by reactions of 1,2-diaza-1,3-butadienes with 1,2-diamines under solution, solvent-free, or solid-phase conditions.

Authors:  Domitila Aparicio; Orazio A Attanasi; Paolino Filippone; Roberto Ignacio; Samuele Lillini; Fabio Mantellini; Francisco Palacios; Jesús M de Los Santos
Journal:  J Org Chem       Date:  2006-08-04       Impact factor: 4.354

5.  Visible-light-induced, copper(I)-catalysed C-N coupling between o-phenylenediamine and terminal alkynes: one-pot synthesis of 3-phenyl-2-hydroxy-quinoxalines.

Authors:  Arunachalam Sagadevan; Ayyakkannu Ragupathi; Kuo Chu Hwang
Journal:  Photochem Photobiol Sci       Date:  2013-12       Impact factor: 3.982

6.  Synthesis and Biological Evaluation of New Quinoxaline Derivatives of ICF01012 as Melanoma-Targeting Probes.

Authors:  Radhia El Aissi; Jianrong Liu; Sophie Besse; Damien Canitrot; Olivier Chavignon; Jean-Michel Chezal; Elisabeth Miot-Noirault; Emmanuel Moreau
Journal:  ACS Med Chem Lett       Date:  2014-02-20       Impact factor: 4.345

7.  The synthesis of benzimidazoles and quinoxalines from aromatic diamines and alcohols by iridium-catalyzed acceptorless dehydrogenative alkylation.

Authors:  Toni Hille; Torsten Irrgang; Rhett Kempe
Journal:  Chemistry       Date:  2014-04-07       Impact factor: 5.236

8.  Novel, low-cost, highly soluble n-type semiconductors: tetraazaanthracene tetraesters.

Authors:  P Gawrys; T Marszalek; E Bartnik; M Kucinska; J Ulanski; M Zagorska
Journal:  Org Lett       Date:  2011-10-26       Impact factor: 6.005

9.  Biosynthetic capacities of actinomycetes. 4. Echinoserine, a new member of the quinoxaline group, produced by Streptomyces tendae.

Authors:  S Blum; H P Fielder; I Groth; C Kempter; H Stephan; G Nicholson; J W Metzger; G Jung
Journal:  J Antibiot (Tokyo)       Date:  1995-07       Impact factor: 2.649

10.  Fragment based design of new H4 receptor-ligands with anti-inflammatory properties in vivo.

Authors:  Rogier A Smits; Herman D Lim; Agnes Hanzer; Obbe P Zuiderveld; Elena Guaita; Maristella Adami; Gabriella Coruzzi; Rob Leurs; Iwan J P de Esch
Journal:  J Med Chem       Date:  2008-03-22       Impact factor: 7.446

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  1 in total

1.  Facile, eco-friendly, catalyst-free synthesis of polyfunctionalized quinoxalines.

Authors:  Yaohong Zhang; Mengqiang Luo; Yan Li; Hai Wang; Xiaorong Ren; Chenze Qi
Journal:  Mol Divers       Date:  2017-10-05       Impact factor: 2.943

  1 in total

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