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Volumn 46, Issue 19, 2005, Pages 3429-3432

A base-catalyzed, direct synthesis of 3,5-disubstituted 1,2,4-triazoles from nitriles and hydrazides

Author keywords

1,2,4 Triazole; Hydrazide; Microwave; Nitriles; Solution phase synthesis

Indexed keywords

HYDRAZIDE DERIVATIVE; NITRILE; TRIAZOLE DERIVATIVE;

EID: 17144393252     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.167     Document Type: Article
Times cited : (96)

References (17)
  • 6
    • 0001184477 scopus 로고
    • A high yielding synthesis of 3,5-disubstituted 1,2,4-triazole from the less reactive amidine has been reported, however, it only applied to acetamidine and benzamidine: J.E. Francis, L.A. Gorczyca, G.C. Mazzenga, and H. Meckler Tetrahedron Lett. 28 1987 5133
    • (1987) Tetrahedron Lett. , vol.28 , pp. 5133
    • Francis, J.E.1    Gorczyca, L.A.2    Mazzenga, G.C.3    Meckler, H.4
  • 7
    • 85030800650 scopus 로고    scopus 로고
    • note
    • In our laboratories, Shimadzu analytical LC/MS and preparative HPLC with auto-sampling are used
  • 8
    • 85030804945 scopus 로고    scopus 로고
    • note
    • The automation capacity of a microwave synthesizer that can be coupled to the Shimadzu instruments is also an attractive feature for this purpose
  • 9
    • 85030796095 scopus 로고    scopus 로고
    • DE Patent 1076136, 1958
    • Neat thermal fusion between benzonitrile (5) and hydrazides at 230°C: Weidinger, H.; Kranz, J. DE Patent 1076136, 1958
    • Weidinger, H.1    Kranz, J.2
  • 10
    • 17144392302 scopus 로고
    • Reaction between benzonitrile (5) and benzoic hydrazide (6) in refluxing MeOH provided a mixture of 1,2,4-triazole (26%) and 1,3,4-oxadiazole (20%): Neelima, and A.P. Bhaduri Indian J. Chem. 22B 1993 79
    • (1993) Indian J. Chem. , vol.22 B , pp. 79
    • Neelima1    Bhaduri, A.P.2
  • 13
    • 0035813242 scopus 로고    scopus 로고
    • 3 was presumably because the equilibration of temperature was equally achieved over the 3 h under both conditions, and assuming equal internal pressure. L. Perreux, and A. Loupy Tetrahedron 57 2001 9199
    • (2001) Tetrahedron , vol.57 , pp. 9199
    • Perreux, L.1    Loupy, A.2
  • 15
    • 85030804757 scopus 로고    scopus 로고
    • note
    • 2O/0.1% TFA). Due to concern about the stability of the hydrazides over the >1 h time period under the basic reaction conditions, 3 equiv of the nitriles were used in all examples. In general, hydrazides show toxicity (e.g., hepatotoxicity), which is usually because of the formation of reactive radical metabolites in vivo
  • 16
    • 85030800135 scopus 로고    scopus 로고
    • note
    • This protocol was found to be incompatible with the presence of nitroaromatic derivatives in either reaction partner. Complex reaction mixtures containing insignificant amounts of product were obtained when either nitrobenzonitrile or nitrobenzoic hydrazide were used


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