Literature DB >> 17109552

Grignard reagent-mediated conversion of an acyl nitroso-anthracene cycloadduct to a nitrone.

Weibin Chen1, Cynthia S Day, S Bruce King.   

Abstract

An intramolecular hetero-Diels-Alder cycloadduct of an acyl nitroso compound and a 9,10-dimethyl anthracene derivative was prepared as a potential nitroxyl (HNO) donor. This compound did not release HNO under any of the conditions tested. Treatment of this cycloadduct with excess MeMgCl resulted in the formation of a nitrone, whose structure was confirmed by X-ray crystallography. A mechanism where MeMgCl acts as a nucleophile, strong base, and Lewis acid possibly explains the formation of this product.

Entities:  

Mesh：

Substances：

Year:  2006        PMID： 17109552      PMCID： PMC3481167          DOI： 10.1021/jo0615192

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


  12 in total

Review 1.  NO news is good news.

Authors:  E Culotta; D E Koshland
Journal:  Science       Date:  1992-12-18       Impact factor: 47.728

Review 2.  The physiological chemistry and biological activity of nitroxyl (HNO): the neglected, misunderstood, and enigmatic nitrogen oxide.

Authors:  Jon M Fukuto; Michael D Bartberger; Andrew S Dutton; Nazareno Paolocci; David A Wink; K N Houk
Journal:  Chem Res Toxicol       Date:  2005-05       Impact factor: 3.739

Review 3.  Donors of HNO.

Authors:  Katrina M Miranda; Herbert T Nagasawa; John P Toscano
Journal:  Curr Top Med Chem       Date:  2005       Impact factor: 3.295

4.  Dual function catalysts. Dehydrogenation and asymmetric intramolecular Diels-Alder cycloaddition of N-hydroxy formate esters and hydroxamic acids: evidence for a ruthenium-acylnitroso intermediate.

Authors:  Chun P Chow; Kenneth J Shea
Journal:  J Am Chem Soc       Date:  2005-03-23       Impact factor: 15.419

5.  Nitric oxide. More jobs for that molecule.

Authors:  S H Snyder
Journal:  Nature       Date:  1994-12-08       Impact factor: 49.962

6.  Human T cells are highly sensitive to suppression of mitogenesis by polycyclic aromatic hydrocarbons and this effect is differentially reversed by alpha-naphthoflavone.

Authors:  D R Davila; D L Romero; S W Burchiel
Journal:  Toxicol Appl Pharmacol       Date:  1996-08       Impact factor: 4.219

7.  Regio- and stereochemically controlled formation of hydroxamic acid containing anti- or syn-1,4-cycloalkenols from acylnitroso-derived Diels-Alder adducts.

Authors:  M D Surman; M J Miller
Journal:  J Org Chem       Date:  2001-04-06       Impact factor: 4.354

8.  Nitroxyl (HNO) release from new functionalized N-hydroxyurea-derived acyl nitroso-9,10-dimethylanthracene cycloadducts.

Authors:  Bu-Bing Zeng; Jinming Huang; Marcus W Wright; S Bruce King
Journal:  Bioorg Med Chem Lett       Date:  2004-11-15       Impact factor: 2.823

9.  Regio- and stereoselective ring openings of 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene systems with copper catalyst-modified grignard reagents: application to the synthesis of an inhibitor of 5-lipoxygenase.

Authors:  Matthew D Surman; Mark J Mulvihill; Marvin J Miller
Journal:  J Org Chem       Date:  2002-06-14       Impact factor: 4.354

10.  Reversible conversion of nitroxyl anion to nitric oxide by superoxide dismutase.

Authors:  M E Murphy; H Sies
Journal:  Proc Natl Acad Sci U S A       Date:  1991-12-01       Impact factor: 11.205
View more
  1 in total

Review 1.  The nitrosocarbonyl hetero-Diels-Alder reaction as a useful tool for organic syntheses.

Authors:  Brian S Bodnar; Marvin J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-21       Impact factor: 15.336
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.