Synthesis of Tris-Heterocycles via a Cascade IMCR/Aza Diels-Alder + CuAAC Strategy
6-Triazolylmethyl-pyrrolo[3,4-b]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/N-acylation/aromatization) followed by a copper-assisted alkyne-azide [3+2] cycloaddition (CuAAC). This efficient and...
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| Format: | Article |
| Language: | English |
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Frontiers Media S.A.
2019-08-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/article/10.3389/fchem.2019.00546/full |
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| author | Manuel A. Rentería-Gómez Alejandro Islas-Jácome Shrikant G. Pharande David A. Vosburg David A. Vosburg Rocío Gámez-Montaño |
| author_facet | Manuel A. Rentería-Gómez Alejandro Islas-Jácome Shrikant G. Pharande David A. Vosburg David A. Vosburg Rocío Gámez-Montaño |
| author_sort | Manuel A. Rentería-Gómez |
| collection | DOAJ |
| description | 6-Triazolylmethyl-pyrrolo[3,4-b]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/N-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 1H-1,2,3-triazoles and pyrrolo[3,4-b]pyridin-5-ones. |
| first_indexed | 2024-12-11T08:58:45Z |
| format | Article |
| id | doaj.art-6deb07ef356745bcad7c596f3967523d |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-11T08:58:45Z |
| publishDate | 2019-08-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-6deb07ef356745bcad7c596f3967523d2022-12-22T01:13:49ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462019-08-01710.3389/fchem.2019.00546464859Synthesis of Tris-Heterocycles via a Cascade IMCR/Aza Diels-Alder + CuAAC StrategyManuel A. Rentería-Gómez0Alejandro Islas-Jácome1Shrikant G. Pharande2David A. Vosburg3David A. Vosburg4Rocío Gámez-Montaño5Departamento de Química, Universidad de Guanajuato, Guanajuato, MexicoDepartamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Mexico City, MexicoDepartamento de Química, Universidad de Guanajuato, Guanajuato, MexicoDepartamento de Química, Universidad de Guanajuato, Guanajuato, MexicoDepartment of Chemistry, Harvey Mudd College, Claremont, CA, United StatesDepartamento de Química, Universidad de Guanajuato, Guanajuato, Mexico6-Triazolylmethyl-pyrrolo[3,4-b]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/N-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 1H-1,2,3-triazoles and pyrrolo[3,4-b]pyridin-5-ones.https://www.frontiersin.org/article/10.3389/fchem.2019.00546/fullnitrogen tris-heterocyclescascade IMCR processCuAACUgi-3CRaza Diels-Alder |
| spellingShingle | Manuel A. Rentería-Gómez Alejandro Islas-Jácome Shrikant G. Pharande David A. Vosburg David A. Vosburg Rocío Gámez-Montaño Synthesis of Tris-Heterocycles via a Cascade IMCR/Aza Diels-Alder + CuAAC Strategy Frontiers in Chemistry nitrogen tris-heterocycles cascade IMCR process CuAAC Ugi-3CR aza Diels-Alder |
| title | Synthesis of Tris-Heterocycles via a Cascade IMCR/Aza Diels-Alder + CuAAC Strategy |
| title_full | Synthesis of Tris-Heterocycles via a Cascade IMCR/Aza Diels-Alder + CuAAC Strategy |
| title_fullStr | Synthesis of Tris-Heterocycles via a Cascade IMCR/Aza Diels-Alder + CuAAC Strategy |
| title_full_unstemmed | Synthesis of Tris-Heterocycles via a Cascade IMCR/Aza Diels-Alder + CuAAC Strategy |
| title_short | Synthesis of Tris-Heterocycles via a Cascade IMCR/Aza Diels-Alder + CuAAC Strategy |
| title_sort | synthesis of tris heterocycles via a cascade imcr aza diels alder cuaac strategy |
| topic | nitrogen tris-heterocycles cascade IMCR process CuAAC Ugi-3CR aza Diels-Alder |
| url | https://www.frontiersin.org/article/10.3389/fchem.2019.00546/full |
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