Synlett 2013; 24(9): 1162-1163
DOI: 10.1055/s-0033-1338942
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© Georg Thieme Verlag Stuttgart · New York

2-Cyanoacetamide

Anna Zdzienicka
Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Łódź, Muszyńskiego 1, 90-151 Łódź, Poland   Email: anna.zdzienicka@umed.lodz.pl
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Further Information

Publication History

Publication Date:
08 May 2013 (online)

Introduction

Cyanoacetic acid derivatives are important intermediates in the synthesis of various organic heterocyclic compounds. Among these derivatives, 2-cyanoacetamide deserves attention since it is a useful reagent for the synthesis of a variety of novel compounds possessing ­biological activity and other special properties.[1]

It possesses electrophilic C1 and C3 carbons and nucleophilic C2 and NH centers responsible for the high reactivity and importance of this compound. The acidic C2 hydrogen prompts an extensive application in a variety of condensation and cycloaddition reactions. Moreover, 2-cyanoacetamide can take part in substitution reactions.[2]

 
  • References

  • 1 Litvinov VP. Russ. Chem. Rev. 1999; 68: 737
  • 2 Fadda AA, Bondock S, Rabie R, Etman HA. Turk. J. Chem. 2008; 32: 259
  • 3 Mateska A, Stojkovic G, Mikhova B, Mladenowska K, Popovski E. ARKIVOC 2009; (x): 131
  • 4 Rubio-Pérez L, Sharma P, Pérez-Flores FJ, Velasco L, Arias JL, Cabrera A. Tetrahedron 2012; 68: 2342
  • 5 Dawadi PB. S, Lugtenburg J. Tetrahedron Lett. 2011; 52: 2508
  • 6 Horiuchi T, Chiba J, Uoto K, Soga T. Bioorg. Med. Chem. Lett. 2009; 19: 305
  • 7 Mukhopadhyay C, Datta A. Synth. Commun. 2008; 38: 2103
  • 8 Bisht SS, Jaiswal N, Sharma A, Fatima S, Sharma R, Rahuja N, Srivastava AK, Baipai V, Kumar B, Tripathi RP. Carbohydr. Res. 2011; 346: 1191
  • 9 Głowacka IE. Tetrahedron: Asymmetry 2009; 20: 2270