Literature DB >> 25838605

Diels-Alder reactions of five-membered heterocycles containing one heteroatom.

Xiaoyuan Ding1, Son T Nguyen1, John D Williams1, Norton P Peet1.   

Abstract

Diels-Alder reactions of five-membered heterocycles containing one heteroatom with an N-arylmaleimide were studied. Cycloaddition of 2,5-dimethylfuran (4) with 2-(4-methylphenyl)maleimide (3) in toluene at 60 °C gave bicyclic adduct 5. Cycloadditions of 3 with 2,5-dimethylthiophene (11) and 1,2,5-trimethylpyrrole (14) were also studied. Interestingly, the bicyclic compound 5 cleanly rearranged, with loss of water, when treated with p-toluenesulfonic acid in toluene at 80 °C to give 4,7-dimethyl-2-p-tolylisoindoline-1,3-dione (6).

Entities:  

Keywords:  Diels-Alder reactions; acid-catalyzed reactions; dienes; dienophiles

Year:  2014        PMID： 25838605      PMCID： PMC4378267          DOI： 10.1016/j.tetlet.2014.10.114

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  6 in total

1.  Chlorin photosensitizers sterically designed to prevent self-aggregation.

Authors:  Adjaci F Uchoa; Kleber T de Oliveira; Mauricio S Baptista; Adailton J Bortoluzzi; Yassuko Iamamoto; Osvaldo A Serra
Journal:  J Org Chem       Date:  2011-10-10       Impact factor: 4.354

2.  Discovery and characterization of inhibitors of Pseudomonas aeruginosa type III secretion.

Authors:  Daniel Aiello; John D Williams; Helena Majgier-Baranowska; Ishan Patel; Norton P Peet; Jin Huang; Stephen Lory; Terry L Bowlin; Donald T Moir
Journal:  Antimicrob Agents Chemother       Date:  2010-02-22       Impact factor: 5.191

3.  Antifungal, cytotoxic and SAR studies of a series of N-alkyl, N-aryl and N-alkylphenyl-1,4-pyrrolediones and related compounds.

Authors:  M Sortino; F Garibotto; V Cechinel Filho; M Gupta; R Enriz; S Zacchino
Journal:  Bioorg Med Chem       Date:  2011-03-23       Impact factor: 3.641

4.  Design and synthesis of 4-[3,5-dioxo-11-oxa-4,9-diazatricyclo[5.3.1.0(2,6)]undec-4-yl]-2-trifluoromethyl-benzonitriles as androgen receptor antagonists.

Authors:  Hai-Yun Xiao; Aaron Balog; Ricardo M Attar; David Fairfax; Linda B Fleming; Christian L Holst; Gregory S Martin; Lana M Rossiter; Jing Chen; Mary-Ellen Cvjic; Janet Dell-John; Jieping Geng; Marco M Gottardis; Wen-Ching Han; Andrew Nation; Mary Obermeier; Cheryl A Rizzo; Liang Schweizer; Thomas Spires; Weifang Shan; Ashvinikumar Gavai; Mark E Salvati; Gregory Vite
Journal:  Bioorg Med Chem Lett       Date:  2010-06-10       Impact factor: 2.823

5.  Identification and optimization of a novel series of [2.2.1]-oxabicyclo imide-based androgen receptor antagonists.

Authors:  Mark E Salvati; Aaron Balog; Weifang Shan; Richard Rampulla; Soren Giese; Tom Mitt; Joseph A Furch; Gregory D Vite; Ricardo M Attar; Maria Jure-Kunkel; Jieping Geng; Cheryl A Rizzo; Marco M Gottardis; Stanley R Krystek; Jack Gougoutas; Michael A Galella; Mary Obermeier; Aberra Fura; Gamini Chandrasena
Journal:  Bioorg Med Chem Lett       Date:  2008-02-08       Impact factor: 2.823

6.  Phosphole-N-phenylmaleimide [4+2] cycloadducts as synthetic equivalents of nucleophilic phosphinidenes.

Authors:  Rongqiang Tian; Zheng Duan; Xiaoxu Zhou; Dingjin Geng; Yangjie Wu; François Mathey
Journal:  Chem Commun (Camb)       Date:  2009-03-26       Impact factor: 6.222
  6 in total
  2 in total

1.  Synthesis of highly substituted benzene ring systems through three-component coupling of enyne imines, Fischer carbene complexes, and electron-deficient alkynes.

Authors:  Bishnu Dhakal; Lalith S R Gamage; Yanshi Zhang; James W Herndon
Journal:  Tetrahedron Lett       Date:  2017-02-24       Impact factor: 2.415

2.  New Experimental Conditions for Diels-Alder and Friedel-Crafts Alquilation Reactions with Thiophene: A New Selenocyanate with Potent Activity against Cancer.

Authors:  Gorka Calvo-Martín; Daniel Plano; Carmen Sanmartín
Journal:  Molecules       Date:  2022-02-01       Impact factor: 4.411
  2 in total

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