D
L. Jarrige et al.
Cluster
Synlett
and 2-methoxythiophene 8c, important heterocycles, could
be also efficiently incorporated into 2a to afford the 9c and
9d respectively, in excellent yields.
(4) For selected recent examples, see: (a) Li, H.; Cheng, P.; Jiang, L.;
Yang, J.-L.; Zu, L. Angew. Chem. Int. Ed. 2017, 56, 2754. (b) Vacala,
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14189.
In conclusion, we have developed a novel NaOH-pro-
moted tandem synthesis of quinolin-2(1H)-ones which in-
volves a Michael addition, aldol cyclization, and elimination
of water.12 This tandem reaction started from readily avail-
able materials under mild reaction conditions to afford
highly functionalized quinolin-2(1H)-ones, which can un-
dergo further transformations into even more complex en-
tities. A plausible mechanism has been proposed for these
tandem reactions. Further investigations regarding the syn-
thetic application of quinolin-2(1H)-ones will be conducted
and published in due course.
Acknowledgment
We thank ICSN and CNRS for financial supports. L.J. thanks Saclay
University for the doctoral fellowships; S.Z thanks Labex Charm3at
for a financial support of Master and J.M. thanks CNRS for the post-
doctoral fellowships.
(5) (a) Gelis, C.; Dumoulin, A.; Bekkaye, M.; Neuville, L.; Masson, G.
Org. Lett. 2017, 19, 278. (b) Jarrige, L.; Levitre, G.; Masson, G.
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Chem. 2016, 81, 10154. (d) Gelis, C.; Bekkaye, M.; Lebée, C.;
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Supporting Information
Supporting information for this article is available online at
S
u
p
p
ortioInfgrmoaitn
S
u
p
p
ortiInfogrmoaitn
(6) The structure of 2h was unambiguously confirmed by X-ray
crystallographic analyses. CCDC 1542892 contains the supple-
mentary crystallographic data for this paper. These data can be
(or from the Cambridge Crystallographic Center, 12 Union Road,
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© Georg Thieme Verlag Stuttgart · New York — Synlett 2017, 28, A–E