Synthesis of Tris-Heterocycles via a Cascade IMCR/Aza Diels-Alder + CuAAC Strategy.

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ID: 14830
2019
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Abstract
6-Triazolylmethyl-pyrrolo[3,4-]pyridin-5-one tris-heterocycles were synthesized in 43-57% overall yields. The two-stage synthesis involved a cascade process (Ugi-3CR/aza Diels-Alder/-acylation/aromatization) followed by a copper-assisted alkyne-azide [3+2] cycloaddition (CuAAC). This efficient and convergent strategy proceeded via complex terminal alkynes functionalized with a fused bis-heterocycle at the α-position. The final products are ideal candidates for SAR studies as they possess two privileged scaffolds in medicinal chemistry: 4-substituted or 1,4-substituted 1-1,2,3-triazoles and pyrrolo[3,4-]pyridin-5-ones.
Reference Key
renteragmez2019synthesisfrontiers Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Rentería-Gómez, Manuel A;Islas-Jácome, Alejandro;Pharande, Shrikant G;Vosburg, David A;Gámez-Montaño, Rocío;
Journal Frontiers in chemistry
Year 2019
DOI
10.3389/fchem.2019.00546
URL
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