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(Reference retrieved automatically from Google Scholar through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Synthesis of 5-alkynyl-2,2,6-trimethyl-1,3-dioxin-4-ones and 1,4-disubstituted-1,2,3-triazoles

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Author(s):
Stefani, Helio A. [1] ; Vieira, Adriano S. [1] ; Amaral, Monica F. Z. J. [1] ; Cooper, Leora [2]
Total Authors: 4
Affiliation:
[1] Univ Sao Paulo, Dept Farm, Fac Ciencias Farmaceut, BR-05508 Sao Paulo - Brazil
[2] Univ Penn, Dept Chem, Philadelphia, PA 19104 - USA
Total Affiliations: 2
Document type: Journal article
Source: Tetrahedron Letters; v. 52, n. 33, p. 4256-4261, 2011.
Web of Science Citations: 12
Abstract

Herein we report an approach to the formation of 5-alkynyl-1,3-dioxin-4-ones using Suzuki-Miyaura cross-coupling reaction of potassium alkynyltrifluoroborate salts with 2,2,6-trimethy1-5-iodo-1,3-dioxin-4-one. The resulting 5-ethynyltrimethylsilyl-1,3-dioxin-4-ones obtained through the Sonogashira reaction were further reacted in a Cu(I)-catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition to form functionalized 1,4-disubstituted-1,2,3-triazoles in good yields, using mild conditions and ultrasonic radiation to expedite the reaction. (C) 2011 Elsevier Ltd. All rights reserved. (AU)

FAPESP's process: 07/02382-7 - Carbohydrates as a chiral pool in organic synthesis: applications in asymmetric catalysis and synthesis of glycopeptides with potential biological activity
Grantee:Diogo Seibert Lüdtke
Support Opportunities: Regular Research Grants