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 - 2014 |
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Keywords
- benzodiazepines
- combinatorial chemistry
- multicomponent reaction
- quinoxalines
- Ugi
ASJC Scopus subject areas
- Organic Chemistry
Cite this
A robust protocol for the synthesis of quinoxalines and 5 H -benzo[ e ][1,4]diazepines via the acidless Ugi reaction. / Ayaz, Muhammad; Martinez-Ariza, Guillermo; Hulme, Christopher.
In: Synlett, Vol. 25, No. 12, 8037, 2014, p. 1680-1684.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - A robust protocol for the synthesis of quinoxalines and 5 H -benzo[ e ][1,4]diazepines via the acidless Ugi reaction
AU - Ayaz, Muhammad
AU - Martinez-Ariza, Guillermo
AU - Hulme, Christopher
PY - 2014
Y1 - 2014
N2 - 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.
AB - 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.
KW - benzodiazepines
KW - combinatorial chemistry
KW - multicomponent reaction
KW - quinoxalines
KW - Ugi
UR - http://www.scopus.com/inward/record.url?scp=84904501044&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84904501044&partnerID=8YFLogxK
U2 - 10.1055/s-0033-1339135
DO - 10.1055/s-0033-1339135
M3 - Article
VL - 25
SP - 1680
EP - 1684
JO - Synlett
JF - Synlett
SN - 0936-5214
IS - 12
M1 - 8037
ER -