Chapter 2 Pyrazol-3-ones. Part IV: Synthesis and Applications

https://doi.org/10.1016/S0065-2725(09)09802-XGet rights and content

Publisher Summary

This chapter focuses on the synthesis and applications of Pyrazol-3-ones. The chapter also highlights the reactions of the ring atoms of pyrazol-3-ones. It explores the reactivity of the ring substituents of pyrazol-3-ones. This chapter illustrates that the majority of pyrazol-3-ones have been synthesized from open chain precursors, and relatively few from5-,6-, 5,6-, 6,6-and 5,6,7-membered rings. Due to the growing use of combinatorial chemistry in various applications, use of polymer-supported methodologies have increased. The oxidation potentials as well as the hydroxyl radical scavenging activities for some pyrazol-3-ones have been detected and compared with edavarone's. The Schiff base 4-[(4-hydroxy-3-hydroxymethylbenzylidene) amino]-1,5-dimethyl-2-phenyl-1,2 dihydropyrazol-3-one retards the corrosion of steel. The chapter concludes that certain azopyrazol-3-ones may prove useful as labels for chromatographic analysis of carbohydrates.

Introduction

The present chapter is Part IV of a four-part series which aims to follow up the major work on pyrazolones published by Wiley and Wiley in The Chemistry of Heterocyclic Compounds series of monographs (64MI1) and specifically comprises an update of Part I. In Part I (01AHC(80)73), the synthesis and applications of pyrazol-3-ones I and II are described covering literature from 1964 up to 2000. In Part II (04AHC(87)141), the reactions of the ring atoms of pyrazol-3-ones I and II are treated for literature from 1964 up to 2003. In Part III (08AHC(95)27), the reactivity of the ring substituents of pyrazol-3-ones I and II has been presented from 1964 up to 2007. The literature of the present chapter (Part IV of the series) has been searched up to December 2008.

Following the trend of Parts I, II and III, and throughout Part IV, all pyrazolones have been named according to the IUPAC recommendations as pyrazol-3-ones and not as pyrazol-5-ones. The IUPAC nomenclature numbers the ring clockwise, whereas most organic chemists are used to an anticlockwise numbering.

Section snippets

Synthesis

Since the publication of Part 1, the majority of pyrazol-3-ones have been synthesized from open chain precursors, and relatively few from 5-, 6-, 5,6-, 6,6- and 5,6,7-membered rings. Moreover, due to the growing use of combinatorial chemistry in various applications, uses of polymer-supported methodologies have increased.

Applications

Pyrazol-3-ones published after 1999 are very versatile compounds and are important as products and intermediates in analytical, dye, biological and pharmaceutical chemistry and as chemicals in photography.

References (168)

  • D. Zimmermann et al.

    Eur. J. Med. Chem.

    (1999)
  • H. Witte-Abel et al.

    J. Organomet. Chem.

    (1999)
  • F. Marchetti et al.

    J. Organomet. Chem.

    (1999)
  • J. Bergman et al.

    Tetrahedron

    (1999)
  • F. Palacios et al.

    Tetrahedron

    (1999)
  • D.E. Kizer et al.

    Tetrahedron Lett.

    (1999)
  • W.C. Kett et al.

    Carbohydr. Res.

    (2000)
  • Yu.G. Shermolovich et al.

    J. Fluorine Chem.

    (2000)
  • X.-C. Tang et al.

    J. Photochem. Photobiol. A: Chem.

    (2000)
  • X.-J. Wang et al.

    Tetrahedron Lett.

    (2000)
  • G. Varvounis et al.

    Adv. Heterocycl. Chem.

    (2001)
  • O.A. Attanasi et al.

    Tetrahedron

    (2001)
  • G. Abbiati et al.

    Tetrahedron

    (2001)
  • O.A. Attanasi et al.

    Tetrahedron

    (2001)
  • F. Al-Omran et al.

    J. Heterocycl. Chem.

    (2002)
  • F. Marchetti et al.

    J. Organomet. Chem.

    (2002)
  • J.C. Jung et al.

    Tetrahedron

    (2002)
  • A. Hameurlaine et al.

    Tetrahedron Lett.

    (2002)
  • S.D. Edmondson et al.

    Bioorg. Med. Chem. Lett.

    (2003)
  • R.H. Wiley et al.

    Pyrazolones, pyrazolidones and derivatives

  • I. Ito et al.

    Chem. Pharm. Bull.

    (1970)
  • W. Nagata et al.

    J. Chem. Soc. (C)

    (1970)
  • J. E. Van Lave, Eastman Kodak Co., US Pat. 3615608...
  • M.H. Elnagdi et al.

    Indian J. Chem.

    (1973)
  • A.M. Qureshi et al.

    Z. Naturforsch.

    (1978)
  • G. Tacconi et al.

    J. Prakt. Chem.

    (1980)
  • N.V. Trofimov et al.

    Zh. Analit. Khim.

    (1982)
  • J. Elguero

    Pyrazoles and their benzo derivatives

  • R.J. Barton et al.

    Can. J. Chem.

    (1987)
  • B.B. Mahapatra et al.

    J. Indian Chem. Soc.

    (1988)
  • A.M.K. El-Dean et al.

    Indian J. Chem., Sect. B

    (1991)
  • W. Holzer et al.

    J. Heterocycl. Chem.

    (1995)
  • N. Ariano et al.

    Jpn. Kokai

    (1996)
  • K.L. Kees et al.

    J. Med. Chem.

    (1996)
  • S.E. De Laslo et al.

    Bioorg. Med. Chem. Lett.

    (1998)
  • S. Wagaw et al.

    J. Am. Chem. Soc.

    (1998)
  • U. Bratušek et al.

    J. Heterocycl. Chem.

    (1998)
  • J. Belmar et al.

    Bol. Soc. Chil. Quim.

    (1999)
  • H. Morita et al.

    J. Heterocycl. Chem.

    (1999)
  • H. Richter et al.

    J. Org. Chem.

    (1999)
  • N. Sventrup et al.

    J. Org. Chem.

    (1999)
  • S.S. Naylan et al.

    Asian J. Chem.

    (1999)
  • Y. Kazuo et al.

    Pestic. Sci.

    (1999)
  • Y.G. Shermolovich et al.

    Russ. J. Org. Chem.

    (1999)
  • V. Kepe et al.

    Heterocycles

    (2000)
  • O. Okitsu et al.

    Heterocycles

    (2000)
  • R. Jain et al.

    J. Indian Chem. Soc.

    (2000)
  • A.M. Abdel-Fattah et al.

    Phosphorus, Sulfur Silicon

    (2000)
  • R. Soliman et al.

    Boll. Chim. Farm.

    (2001)
  • J. Belmar et al.

    Bol. Soc. Chil. Quim.

    (2001)

    • Cited by (0)

    View full text
    Copyright © 2009 Elsevier Inc. All rights reserved.