Abstract
Concise two-step, one-pot protocols for the syntheses of quinoxalines and 5H-benzo[e][1,4]diazepines are reported. An 'acidless' Ugi reaction followed by a Boc-deprotection-cyclization sequence is shown to produce arrays of both functionalized scaffolds in good yield. Mono-N-Boc-protected diamines are employed to access quinoxalines and an analogous benzylic amine affords access to 5H-benzo[e][1,4]diazepines in conjunction with supporting reagents in the 'acidless' Ugi reaction. Both methodologies are robust, straightforward, and allow installation of at least three points of diversity in the resulting scaffolds.
| Original language | English (US) |
|---|---|
| Article number | 8037 |
| Pages (from-to) | 1680-1684 |
| Number of pages | 5 |
| Journal | Synlett |
| Volume | 25 |
| Issue number | 12 |
| DOIs | |
| State | Published - Jul 2014 |
Keywords
- Ugi
- benzodiazepines
- combinatorial chemistry
- multicomponent reaction
- quinoxalines
ASJC Scopus subject areas
- Organic Chemistry
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Ayaz, M., Martinez-Ariza, G., & Hulme, C. (2014). A robust protocol for the synthesis of quinoxalines and 5 H -benzo[ e ][1,4]diazepines via the acidless Ugi reaction. Synlett, 25(12), 1680-1684. [8037]. https://doi.org/10.1055/s-0033-1339135