Abstract
The Doebner-Miller synthesis of quinolines under modified biphasic conditions was investigated. Crotonaldehyde, reacted readily with aniline to produce 2-methylquinoline. However, cinnamaldehyde and other γ-substituted α,β-unsaturated aldehydes yielded complex mixtures with substituted anilines to provide only trace quantities of quinolines. The Doebner-Miller reaction under these conditions is only suitable for sterically accessible α,β-unsaturated aldehydes.
| Original language | English |
|---|---|
| Article number | P11410SS |
| Pages (from-to) | 3645-3648 |
| Number of pages | 4 |
| Journal | Synthesis |
| Volume | 2010 |
| Issue number | 21 |
| DOIs | |
| Publication status | Published - Nov 2010 |
| Externally published | Yes |
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Limitations of the two-phase doebner-miller reaction for the synthesis of quinolines. / Reynolds, Kristie A.; Young, David J.; Loughlin, Wendy A.
In: Synthesis, Vol. 2010, No. 21, P11410SS, 11.2010, p. 3645-3648.Research output: Contribution to journal › Article › Research › peer-review
TY - JOUR
T1 - Limitations of the two-phase doebner-miller reaction for the synthesis of quinolines
AU - Reynolds, Kristie A.
AU - Young, David J.
AU - Loughlin, Wendy A.
PY - 2010/11
Y1 - 2010/11
N2 - The Doebner-Miller synthesis of quinolines under modified biphasic conditions was investigated. Crotonaldehyde, reacted readily with aniline to produce 2-methylquinoline. However, cinnamaldehyde and other γ-substituted α,β-unsaturated aldehydes yielded complex mixtures with substituted anilines to provide only trace quantities of quinolines. The Doebner-Miller reaction under these conditions is only suitable for sterically accessible α,β-unsaturated aldehydes.
AB - The Doebner-Miller synthesis of quinolines under modified biphasic conditions was investigated. Crotonaldehyde, reacted readily with aniline to produce 2-methylquinoline. However, cinnamaldehyde and other γ-substituted α,β-unsaturated aldehydes yielded complex mixtures with substituted anilines to provide only trace quantities of quinolines. The Doebner-Miller reaction under these conditions is only suitable for sterically accessible α,β-unsaturated aldehydes.
KW - α,β,-unsaturated aldehyde
KW - aniline
KW - Doebner-Miller reaction
KW - heterocycle
KW - quinoline
UR - http://www.scopus.com/inward/record.url?scp=77958529214&partnerID=8YFLogxK
U2 - 10.1055/s-0030-1258258
DO - 10.1055/s-0030-1258258
M3 - Article
VL - 2010
SP - 3645
EP - 3648
JO - Synthesis: journal of synthetic organic chemistry
JF - Synthesis: journal of synthetic organic chemistry
SN - 0039-7881
IS - 21
M1 - P11410SS
ER -