Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2010 Oct 27;51(43):5740-5743.
doi: 10.1016/j.tetlet.2010.08.083. Epub 2010 Sep 1.

Facile route for N 1-aryl benzotriazoles from diazoamino arynes via CuI-mediated intramolecular N-arylation

Raju R Kale  1 , Virendra Prasad  1 , H A Hussain  1 , Vinod K Tiwari  1
Affiliations

Facile route for N 1-aryl benzotriazoles from diazoamino arynes via CuI-mediated intramolecular N-arylation

Raju R Kale et al. Tetrahedron Lett. .

Abstract

A facile and high-yielding protocol for diverse benzotriazoles through intramolecular N-arylation of different o-chloro-1,2,3-benzotriazenes using CuI/Cs2CO3 has been developed.

Keywords: Amines; Benzotriazole; CuI; Diazonium salt; N-Arylation.

PubMed Disclaimer

Figures

None
Graphical abstract
Scheme 1
Scheme 1
Synthesis of N1-benzotriazole under Click reaction condition.
Scheme 2
Scheme 2
Synthesis of N1-substituted benzotriazoles via intramolecular N-arylation.
See this image and copyright information in PMC

References

    1. Carlini R., Bria E., Giannarelli D., Ferretti G., Felici A., Papaldo P., Fabi A., Nistico C., Cosimo S. Di.; Ruggeri, E. M.; Milella, M.; Mottolese, M.; Terzoli, E.; Cognetti, F. Cancer. 2005;104:1335–1557. - PubMed
    2. Semple G., Skinner P.J., Cherrier M.C., Webb P.J., Sage C.R., Tamura S.Y., Chen R., Richman J.G., Connolly D.T. J. Med. Chem. 2006;49:1227–1230. - PubMed
    1. Dipesa A.J., Donahue K.M., Dombroski M.A., Elliott N.C., Gabel C.A., Han S., Hynes T.R., LeMotte P.K., Mansour M.N., Marr E.S., Letavic M.A., Pandit J., Ripin D.B., Sweeney F.J., Tan D., Tao Y. J. Med. Chem. 2005;48:5728–5737. - PubMed
    2. Wu C.Y., King K.Y., Fang J.M., Wu Y.T., Ho M.Y., Liao C.L., Shie J., Liang P.H., Wong C.H. Chem. Biol. 2006;13:261–268. - PMC - PubMed
    3. Katritzky A.R., Jiang J., Urogdi L. Tetrahedron Lett. 1989;25:3303–3306.
    4. Wender P.A., Touami S.M., Alayrac C., Philipp U.C. J. Am. Chem. Soc. 1996;118:6522–6523.
    5. Caliendo G., Greco G., Grieco P., Novellino E., Perissuttil E., Santagada V., Barbarul D., Esposit E., De Blas A. Eur. J. Med. Chem. 1996;31:207–213.
    1. Katritzky A.R., Lan X., Jason Z., Yang Z., Denisko O.V. Chem. Rev. 1998;98:409–548. - PubMed
    2. Katritzky A.R., Manju K., Singh S.K., Meher N.K. Tetrahedron. 2005;61:2555–2581.
    3. Katritzky A.R., Rogovoy B.V. Chem. Eur. J. 2003;19:4586–4593. - PubMed
    4. Katritzky A.R., Lan X. Chem. Soc. Rev. 1994;23:363–373.
    5. Katritzky A.R., Henderson S.A., Yang B. J. Heterocycl. Chem. 1998;35:1123–1159.
    1. Verma A.K., Kesharwani T., Singh J., Tandon V., Larock R.C. Angew. Chem., Int. Ed. 2009;48:1138–1143. - PubMed
    2. Kale R.R., Prasad V., Mohapatra P.P., Tiwari V.K. Monatsh. Chem. 2010
    1. Reynolds G.A. J. Org. Chem. 1964;29:3733–3734.

LinkOut - more resources