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Volumn 46, Issue 21, 2007, Pages 3926-3930

Cu2(OTf)2-catalyzed and microwave-controlled preparation of tetrazoles from nitriles and organic azides under mild, safe conditions

Author keywords

Azides; Copper; Cycloaddition; Homogeneous catalysis; Tetrazoles

Indexed keywords

CATALYSIS; COPPER COMPOUNDS; CYCLOADDITION; HAZARDS; HEATING; MICROWAVES;

EID: 34250760405     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200605095     Document Type: Article
Times cited : (114)

References (48)
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    • The direct reaction of organic nitriles with the azide ion, when N-unsubstituted tetrazoles are aimed for, is much more common and easier to accomplish but poses other well-known safety requirements or handicaps (including the explosive nature of many transition-metal azides in catalytic reactions). For an additional review, see: V. Y. Zubarev, V. A. Ostrovskii, Chem. Heterocycl. Compd. 2000, 36, 759.
    • c) The direct reaction of organic nitriles with the azide ion, when N-unsubstituted tetrazoles are aimed for, is much more common and easier to accomplish but poses other well-known safety requirements or handicaps (including the explosive nature of many transition-metal azides in catalytic reactions). For an additional review, see: V. Y. Zubarev, V. A. Ostrovskii, Chem. Heterocycl. Compd. 2000, 36, 759.
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    • f) H. C. Kolb, K. B. Sharpless, Drug Discovery Today 2003, 8, 1128. A search through SciFinder in December 2006 indicates the growing number of articles that are being published on click chemistry applications (126 in 2006, 59 in 2005, 26 in 2004, 5 in 2003).
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    • For spectra of the two corresponding N-benzyl tetrazoles, see: W. Holzer, C. Jäger, Monatsh. Chem. 1992, 123, 1027.
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    • At concentrations of 0.1M. Either at higher concentrations, by concentrating the final mixture in the rotary evaporator, or when larger amounts of pyrrolidine are used, deacetylation also occurs during this step
    • At concentrations of 0.1M. Either at higher concentrations, by concentrating the final mixture in the rotary evaporator, or when larger amounts of pyrrolidine are used, deacetylation also occurs during this step.
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    • 6]DMSO, H5″ (tetrazole ring) at δ = 9.56 ppm and C5″ at δ = 143.6 ppm. See the Supporting Information for the full spectra. This compound (14) and related derivatives (not substituted at C5″) had not been reported, to our knowledge. By opening anhydrothymidine with the tetrazolate anion, on heating at 120°C, only its 1,4-disubstituted isomer (the 2-tetrazolyl derivative) was obtained, as we have confirmed; See: A. A. Malin, V. A. Ostrovskii, Russ. J. Org. Chem. 2001, 37, 759.
    • 6]DMSO, H5″ (tetrazole ring) at δ = 9.56 ppm and C5″ at δ = 143.6 ppm. See the Supporting Information for the full spectra. This compound (14) and related derivatives (not substituted at C5″) had not been reported, to our knowledge. By opening anhydrothymidine with the tetrazolate anion, on heating at 120°C, only its 1,4-disubstituted isomer (the 2-tetrazolyl derivative) was obtained, as we have confirmed; See: A. A. Malin, V. A. Ostrovskii, Russ. J. Org. Chem. 2001, 37, 759.
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    • Throughout the more than thirty years in which organic azides have been used in our lab from time to time [see, e.g, M. Rull, J. Vilarrasa, Tetrahedron Lett. 1976, 17, 4175;
    • Throughout the more than thirty years in which organic azides have been used in our lab from time to time [see, e.g.: M. Rull, J. Vilarrasa, Tetrahedron Lett. 1976, 17, 4175;
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    • 2, see: N. P. Peet, P. M. Weintraub, Chem. Eng. News 1994, 72(11), 4, and references therein;


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