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:	Creators Email Pitt Username ORCID Wang, XJ Zhang, L Krishnamurthy, D Senanayake, CH Wipf, P pwipf@pitt.edu PWIPF
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-dev.library.pitt.edu/id/eprint/18775

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