Literature DB >> 26257574

Heterocycle-to-Heterocycle Route to Quinoline-4-amines: Reductive Heterocyclization of 3-(2-Nitrophenyl)isoxazoles.

Keith C Coffman1, Vy Duong1, Alex L Bagdasarian1, James C Fettinger1, Makhlouf J Haddadin2, Mark J Kurth1.   

Abstract

A variety of quinoline-4-amines were synthesized from substituted 3-(2-nitrophenyl)isoxazoles utilizing Zn0 or Fe0 dust and HOAc via a reductive heterocyclization process. The starting isoxazoles were synthesized from readily available starting materials. A brief survey of functional groups tolerated in this reductive heterocyclization was performed and several 10-amino-3,4-dihydrobenzo[b][1,6]naphthyridin-1(2H)-one and 9-amino-3,4-dihydroacridin-1(2H)-one examples were synthesized.

Entities:  

Keywords:  Diversity Oriented Synthesis; Fused-ring systems; Heterocycle; Heterocyclization; Reduction

Year:  2014        PMID： 26257574      PMCID： PMC4524663          DOI： 10.1002/ejoc.201403065

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  13 in total

1.  Orthogonally protected thiazole and isoxazole diamino acids: an efficient synthetic route.

Authors:  Jeffrey D Butler; Keith C Coffman; Kristin T Ziebart; Michael D Toney; Mark J Kurth
Journal:  Chemistry       Date:  2010-08-09       Impact factor: 5.236

2.  Synthesis of isoxazoles by hypervalent iodine-induced cycloaddition of nitrile oxides to alkynes.

Authors:  Anup M Jawalekar; Erik Reubsaet; Floris P J T Rutjes; Floris L van Delft
Journal:  Chem Commun (Camb)       Date:  2011-02-01       Impact factor: 6.222

3.  Total synthesis and absolute stereochemistry of seragakinone A.

Authors:  Akiomi Takada; Yoshimitsu Hashimoto; Hiroshi Takikawa; Katsuyoshi Hikita; Keisuke Suzuki
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-03       Impact factor: 15.336

4.  Development of a new generation of 4-aminoquinoline antimalarial compounds using predictive pharmacokinetic and toxicology models.

Authors:  Sunetra Ray; Peter B Madrid; Paul Catz; Susanna E LeValley; Michael J Furniss; Linda L Rausch; R Kiplin Guy; Joseph L DeRisi; Lalitha V Iyer; Carol E Green; Jon C Mirsalis
Journal:  J Med Chem       Date:  2010-05-13       Impact factor: 7.446

5.  Synthesis and biological evaluation of a series of aminoalkyl-tetralones and tetralols as dual dopamine/serotonin ligands.

Authors:  Laura Carro; María Torrado; Enrique Raviña; Christian F Masaguer; Sonia Lage; José Brea; María I Loza
Journal:  Eur J Med Chem       Date:  2013-11-20       Impact factor: 6.514

6.  Isoxazole --> benzisoxazole rearrangement promoted cascade reactions affording stereodefined polycycles.

Authors:  Jeffrey W Bode; Hidehiro Uesuka; Keisuke Suzuki
Journal:  Org Lett       Date:  2003-02-20       Impact factor: 6.005

7.  Facile construction and divergent transformation of polycyclic isoxazoles: direct access to polyketide architectures.

Authors:  Jeffrey W Bode; Yoshifumi Hachisu; Tomoo Matsuura; Keisuke Suzuki
Journal:  Org Lett       Date:  2003-02-20       Impact factor: 6.005

8.  Isoxazolodihydropyridinones: 1,3-dipolar cycloaddition of nitrile oxides onto 2,4-dioxopiperidines.

Authors:  Keith C Coffman; Timothy P Hartley; Jerry L Dallas; Mark J Kurth
Journal:  ACS Comb Sci       Date:  2012-03-16       Impact factor: 3.784

9.  Heterocycle-heterocycle strategies: (2-nitrophenyl)isoxazole precursors to 4-aminoquinolines, 1H-indoles, and quinolin-4(1H)-ones.

Authors:  Keith C Coffman; Teresa A Palazzo; Timothy P Hartley; James C Fettinger; Dean J Tantillo; Mark J Kurth
Journal:  Org Lett       Date:  2013-04-04       Impact factor: 6.005

10.  Structure-activity relationship (SAR) optimization of 6-(indol-2-yl)pyridine-3-sulfonamides: identification of potent, selective, and orally bioavailable small molecules targeting hepatitis C (HCV) NS4B.

Authors:  Nanjing Zhang; Xiaoyan Zhang; Jin Zhu; Anthony Turpoff; Guangming Chen; Christie Morrill; Song Huang; William Lennox; Ramesh Kakarla; Ronggang Liu; Chunshi Li; Hongyu Ren; Neil Almstead; Srikanth Venkatraman; F George Njoroge; Zhengxian Gu; Valerie Clausen; Jason Graci; Stephen P Jung; Yingcong Zheng; Joseph M Colacino; Fred Lahser; Josephine Sheedy; Anna Mollin; Marla Weetall; Amin Nomeir; Gary M Karp
Journal:  J Med Chem       Date:  2013-12-04       Impact factor: 7.446
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  2 in total

1.  Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis-Beirut Reaction.

Authors:  Jie S Zhu; Jung-Ho Son; Andrew P Teuthorn; Makhluf J Haddadin; Mark J Kurth; Dean J Tantillo
Journal:  J Org Chem       Date:  2017-09-28       Impact factor: 4.354

2.  Dibenzonaphthyridinones: Heterocycle-to-Heterocycle Synthetic Strategies and Photophysical Studies.

Authors:  Teresa A Palazzo; Digambara Patra; Joung S Yang; Elsy El Khoury; Mackenzie G Appleton; Makhluf J Haddadin; Dean J Tantillo; Mark J Kurth
Journal:  Org Lett       Date:  2015-11-17       Impact factor: 6.005
  2 in total

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