Acid-catalyzed [2 + 2 + 2] cycloaddition of two cyanamides and one ynamide : highly regioselective synthesis of 2,4,6-triaminopyrimidines
Triflic acid (10 mol%) catalyzes the highly regioselective [2 + 2 + 2] cycloaddition between two cyanamides and one ynamide to grant the 2,4,6-triaminopyrimidine core. The developed synthetic method is effective for the preparation of a family of the diversely substituted heterocyclic products (30 examples; yields up to 94%). The synthesis can be easily scaled up and conducted in gram quantities. As demonstrated by the post-functionalizations involving the amino-substituents, the obtained heterocycles represent a useful platform for the construction of miscellaneous pyrimidine-based frameworks. The performed density functional theory calculations verified a particular role of H+, functioning as an electrophilic activator, in the regioselectivity of the cycloaddition.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2021 |
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| Erschienen: |
2021 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:19 |
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| Enthalten in: |
Organic & biomolecular chemistry - 19(2021), 20 vom: 26. Mai, Seite 4577-4584 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Dubovtsev, Alexey Yu [VerfasserIn] |
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| Links: |
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| Themen: |
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| Anmerkungen: |
Date Completed 11.03.2022 Date Revised 11.03.2022 published: Print Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1039/d1ob00513h |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM32506881X |
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| 100 | 1 | |a Dubovtsev, Alexey Yu |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Acid-catalyzed [2 + 2 + 2] cycloaddition of two cyanamides and one ynamide |b highly regioselective synthesis of 2,4,6-triaminopyrimidines |
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| 500 | |a Date Completed 11.03.2022 | ||
| 500 | |a Date Revised 11.03.2022 | ||
| 500 | |a published: Print | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a Triflic acid (10 mol%) catalyzes the highly regioselective [2 + 2 + 2] cycloaddition between two cyanamides and one ynamide to grant the 2,4,6-triaminopyrimidine core. The developed synthetic method is effective for the preparation of a family of the diversely substituted heterocyclic products (30 examples; yields up to 94%). The synthesis can be easily scaled up and conducted in gram quantities. As demonstrated by the post-functionalizations involving the amino-substituents, the obtained heterocycles represent a useful platform for the construction of miscellaneous pyrimidine-based frameworks. The performed density functional theory calculations verified a particular role of H+, functioning as an electrophilic activator, in the regioselectivity of the cycloaddition | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 700 | 1 | |a Zvereva, Valeria V |e verfasserin |4 aut | |
| 700 | 1 | |a Shcherbakov, Nikolay V |e verfasserin |4 aut | |
| 700 | 1 | |a Dar'in, Dmitry V |e verfasserin |4 aut | |
| 700 | 1 | |a Novikov, Alexander S |e verfasserin |4 aut | |
| 700 | 1 | |a Kukushkin, Vadim Yu |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Organic & biomolecular chemistry |d 2003 |g 19(2021), 20 vom: 26. Mai, Seite 4577-4584 |w (DE-627)NLM126779694 |x 1477-0539 |7 nnns |
| 773 | 1 | 8 | |g volume:19 |g year:2021 |g number:20 |g day:26 |g month:05 |g pages:4577-4584 |
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