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General solution to the synthesis of N-2-substituted 1,2,3-triazoles

Wang, XJ and Zhang, L and Krishnamurthy, D and Senanayake, CH and Wipf, P (2010) General solution to the synthesis of N-2-substituted 1,2,3-triazoles. Organic Letters, 12 (20). 4632 - 4635. ISSN 1523-7060

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Abstract

The regioselective N-alkylation of 1,2,3-triazoles 1 - 6 was studied. Good to excellent N-2 selectivity and high chemical yields for N-2-substituted 4,5-dibromotriazoles 7 were obtained with 4,5-dibromo- and 4-bromo-5- trimethylsilyl-1,2,3-triazoles. These building blocks can be readily converted to 2-mono-, 2,4-di-, and 2,4,5-polysubstituted triazoles 10 - 15, providing a general, protective, group-free method for the synthesis of N-2-substituted triazoles. Observed regioselectivities can be rationalized by a combination of Frontier Molecular Orbital, steric, and electrostatic directing effects on the heterocyclic scaffolds. © 2010 American Chemical Society.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Wang, XJ
Zhang, L
Krishnamurthy, D
Senanayake, CH
Wipf, Ppwipf@pitt.eduPWIPF
Date: 15 October 2010
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 12
Number: 20
Page Range: 4632 - 4635
DOI or Unique Handle: 10.1021/ol101965a
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Alkylation; Models, Molecular; Molecular Structure; Static Electricity; Triazoles--chemical synthesis
PubMed ID: 20863126
Date Deposited: 28 May 2013 15:31
Last Modified: 04 Feb 2019 15:56
URI: http://d-scholarship.pitt.edu/id/eprint/18775

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