Synlett 2014; 25(11): 1631-1632
DOI: 10.1055/s-0034-1378211
spotlight
© Georg Thieme Verlag Stuttgart · New York

Acid Hydrazides

Twinkle Keshari
Green Synthesis Lab, Department of Chemistry, University of Allahabad, Allahabad 211 002, India    eMail: twinkle31081989@hotmail.com
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
26. Mai 2014 (online)

Introduction

Acid hydrazides are organic derivatives of hydrazine. Transformations using these species to synthesize heterocycles have been research objectives for over a century.[1] Because of their wide utility, acid hydrazides have always been attractive precursors for the synthesis of heterocycles. They have been used for the synthesis of five- and six-membered heterocycles incorporating two or more heteroatoms in the ring, such as indoles, pyrazoles, oxadiazoles, and triazoles which display a wide spectrum of biological activities.[2] Hydrazide analogues[3] also possess useful biological activities.[4] Isonicotinic acid hydrazide has been used in medical practice.[5] In organic synthesis, acid hydrazides have similarities with Weinreb amides, as plenty of sites are available for forming a stable metal chelate. Thus, they are used as effective acyl donors for the synthesis of ketones[6] and amides.[7] Acid hydrazides can be easily prepared by the combination of hydrazine with various acyl derivatives, including esters, cyclic anhydrides, and acyl halides.

 
  • References

  • 1 Majumdar P, Pati A, Patra M, Behera RK, Behera AK. Chem. Rev. 2014; 114: 2942
    • 2a Isloor AM, Kalluraya B, Sridhar PaiK. Eur. J. Med. Chem. 2010; 45: 825
    • 2b Rostom SA. F. Bioorg. Med. Chem. 2010; 18: 2767
    • 2c Sangshetti JN, Chabukswar AR, Shnide DB. Bioorg. Med. Chem. Lett. 2011; 21: 444
  • 3 Kumar P, Narasimhan B, Sharma D. ARKIVOC 2008; (viii): 159
    • 4a Bijev A. Lett. Drug Des. Discov. 2006; 3: 506
    • 4b Ragavendran J, Sriram D, Patel S, Reddy I, Bharathwajan N, Stables J, Yogeeswari P. Eur. J. Med. Chem. 2007; 42: 146
    • 4c Gursoy E, Guzeldimirci-Ulusoy N. Eur. J. Med. Chem. 2007; 42: 320
    • 4d Masunari A, Tavaris LC. Bioorg. Med. Chem. 2007; 15: 4229
  • 5 Ukrainets IV, Tkach AA, Mospanova EV, Svechnikova EN. Chem. Heterocycl. Compd. 2007; 43: 1014
  • 6 Akhbar AR, Chudasama V, Fitzmaurice JR, Powell L, Caddick S. Chem. Commun. 2014; 50: 743
  • 7 Chudasama V, Fitzmaurice RJ, Dhokia DV, Ahern JM, Caddick S. Chem. Commun. 2011; 47: 3269
  • 8 Yadav AK, Yadav LD. S. Tetrahedron Lett. 2014; 55: 2065
  • 9 Guda RD, Cho MH, Lee ME. RSC Adv. 2013; 3: 6813
  • 10 Guo S, Wang J, Guo D, Zhang X, Fan X. Tetrahedron 2012; 68: 7768
  • 11 Guin S, Rout SK, Khatun N, Ghosh T, Patel BK. Tetrahedron 2012; 68: 5066
  • 12 Hisler K, Commeureuc AG. J, Zhou S.-J, Murphy JA. Tetrahedron Lett. 2009; 50: 3290