Functionalization of 2-(S)-isopropyl-5-iodo-pyrimidin-4-ones through Cu(I)-mediated 1,3-dipolar azide-alkyne cycloadditions

TETRAHEDRON LETTERS

卷:52

Article

Stefani, Helio A.¹  Amaral, Monica F. Z. J.¹  Manarin, Flavia¹  Ando, Romulo A.²  Silva, Nathalia C. S.¹  Juaristi, Eusebio³ 

[1] Univ Sao Paulo, Fac Ciencias Farmaceut, BR-05508000 Sao Paulo, Brazil

[2] Univ Sao Paulo, Inst Quim, Sao Paulo, Brazil

[3] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07000, DF, Mexico

关键词: Pyrimidinones;    1,2,3-Triazole;    Cycloaddition;    Sonogashira reaction;    Click chemistry;   

DOI  :  10.1016/j.tetlet.2011.10.011

来源: Elsevier

【 摘 要 】

A series of 2-(S)-isopropyl-pyrimidinones functionalized at C5 with triazole rings, in which the substituents are found at N-1' of the triazole ring, were synthesized. Through the azide-acetylene cycloaddition reaction, using Cul as a copper source and ultrasonic waves as an energy source it was possible to obtain products with yields ranging from 79% to 89% within 5 min or less. A preliminary study to gain further insight into the reaction was performed using in situ ReactIR technology. (C) 2011 Elsevier Ltd. All rights reserved.

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