AUTHOR=Rentería-Gómez Manuel A. , Islas-Jácome Alejandro , Pharande Shrikant G. , Vosburg David A. , Gámez-Montaño Rocío 

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

JOURNAL=Frontiers in Chemistry

VOLUME=7

YEAR=2019

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2019.00546

DOI=10.3389/fchem.2019.00546

ISSN=2296-2646

ABSTRACT=<p>6-Triazolylmethyl-pyrrolo[3,4-<italic>b</italic>]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/<italic>N</italic>-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<italic>H</italic>-1,2,3-triazoles and pyrrolo[3,4-<italic>b</italic>]pyridin-5-ones.</p>