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
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Status: |
Published |
Creators/Authors: |
Creators | Email | Pitt Username | ORCID  |
---|
Wang, XJ | | | | Zhang, L | | | | Krishnamurthy, D | | | | Senanayake, CH | | | | Wipf, P | pwipf@pitt.edu | PWIPF | |
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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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