Communication
ChemComm
Table 1 One-pot multicomponent reactions of aromatic/aliphatic amines,
aromatic aldehydes and b-ketoesters catalysed by ZnO nanoparticles
M.K. and V.B. are thankful to UGC [ref. no. 42-282/2013(SR)]
and CSIR (ref. no. 02(0083)/12/EMR-II) for financial support,
respectively. We are also thankful to UGC for the UPE project.
Meenal Kataria is thankful to DST for the INSPIRE fellowship.
Melting
Time Yield point
R
1
R
2
R
3
Product
Sr. No. (6a–b) (7a–b) (8a–d)
12a–f Temp. (h) (%) (1C)
Notes and references
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–
6
CH
a
3
1
2
3
4
12a
12b
12c
12d
RT
2.5 91
189–190
229–230
212–213
200–202
–
C
2
H
5
RT
3
3
5
9
89
89
85
6
b
3
(a) M. Yoshida, K. Kinoshita and K. Namba, Org. Biomol. Chem.,
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–
CH
3
RT
Ed., 2008, 47, 4851.
R. Chen, S. Xu, L. Wang, Y. Tang and Z. He, Chem. Commun., 2013,
6
a
4
49, 3543.
–
CH
3
5 X. Li, Y. Zhao, H. Qu, Z. Mao and X. Lin, Chem. Commun., 2013,
49, 1401.
RT
6
a
6
(a) Y. Li, X. M. Hong, D. M. Collard and M. A. E. Sayed, Org. Lett.,
000, 15, 2385; (b) S. Pramanik, V. Bhalla and M. Kumar, Chem.
2
–
CH
3
5
6
12e
12f
50 1C
80
63
255–256
150–151
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6
a
7
(a) A. D. Finke and F. Diederich, Chem. Rec., 2014, DOI: 10.1002/
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–
CH
3
nBu–7b
50 1C 12
6
a
8
9
(a) A. D. Finke, O. Dumele, M. Zalibera, D. Confortin, P. Cias,
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b-ketoester furnishes intermediate enamine 9, which reacts with
the aromatic aldehyde to afford intermediate 10. In step-II, the
reaction between the amine and the aromatic aldehyde furnishes
intermediate Schiff base 11. In the final step, intermediate 10
tautomerizes and undergoes intermolecular cyclization with 11
to yield the corresponding tetrahydropyridine derivatives 12a–f.
(
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We separately synthesized these three derivatives 9, 10 and 11,
1
whose structures were confirmed by H NMR (Fig. S29 and S30, 11 S. K. Park, J. H. Park, K. Y. Ko, S. Yoon, K. S. Chu, W. Kim and
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ESI†) and consequently mixed them to get tetrahydropyridine
1
1
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through these three steps with the formation of intermediates 9–11.
We also carried out the one-pot Mannich reaction of 4-chloro-
benzaldehyde, aniline and cyclohexanone (1 : 1 : 1) by using the
ZnO nanoparticles and product 13 was obtained in 96% yield at
room temperature (Fig. S31, ESI†). Therefore, this new catalytic
system probably works well for the multicomponent as well as
three-component reactions.
1
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fulvene derivative 4 having b-naphthol groups which formed fluor-
escent aggregates in aqueous media due to its AIEE characteristics.
5
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2+
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These aggregates showed high affinity towards Zn ions and served
as reactors and stabilizers for the preparation of ZnO nanoparticles
at room temperature and exhibited ZnO NP-induced emission
enhancement. Further, in situ generated ZnO NPs showed excellent
catalytic activity in one-pot, multicomponent reactions for the pre-
paration of tetrahydropyridine derivatives, 12a–f.
1
2
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2
2
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1
486 | Chem. Commun., 2015, 51, 1483--1486
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