S. M. Roopan, F. R. N. Khan/Chemical Papers 64 (5) 678–682 (2010)
681
O
O
+ KOH
N
N
H
ZnO nanorod
N
Cl
N
A
+ H2O
Va
O
Cl
Cl
N
K+
KCl
IIIa
Fig. 3. Role of ZnO nanorods in the synthesis of N-alkylated products.
conditions iv in Fig. 1) produce intermediate A (see
Fig. 3) which can be further involved in the coupling
of arylalkyl chloride IIIa to give product Va (Fig. 3).
In this communication, a simple method of the N-
alkylation of some heterocycles using ZnO nanorods is
reported. A simple experimental procedure combined
with an easy workup and excellent yields of products
are salient features of the presented method.
Khan, F. N., Subashini, R., Roopan, S. M., Hathwar, V.
R., & Ng, S. W. (2009b). 2-Chloro-6-methylquinoline-3-
carbaldehyde. Acta Crystallographica Section E, E65, o2686.
DOI: 10.1107/S1600536809040653.
Manivel, P., Roopan, S. M., & Khan, F. N. (2008). Syn-
thesis of O-substituted benzophenones by Grignard reac-
tion of 3-substituted isocoumarins. Journal of the Chilean
Chemical Society, 53, 1609–1610. DOI: 10.4067/S0717-
97072008000300012.
Manivel, P., Roopan, S. M., Kumar, D. P., & Khan, F. N.
(2009). Isocoumarin thioanalogues as potential antibacterial
agents. Phosphorus, Sulfur, and Silicon and the Related El-
ements, 184, 2576–2582. DOI: 10.1080/10426500802529507.
Mirjafary, Z., Saeidian, H., Sadeghi, A., & Moghaddam, F.
M. (2008). ZnO nanoparticles: An efficient nanocatalyst for
the synthesis of β-acetamido ketones/esters via a multi-
component reaction. Catalysis Communications, 9, 299–306.
DOI: 10.1016/j.catcom.2007.06.018.
Nacro, K., Zha, C., Guzzo, P. R., Herr, R. J., Peace, D., &
Friedrich, T. D. (2007). Synthesis and topoisomerase poi-
soning activity of A-ring and E-ring substituted luotonin A
derivatives. Bioorganic & Medicinal Chemistry, 15, 4237–
4246. DOI: 10.1016/j.bmc.2007.03.067.
Richards, R., Li, W., Decker, S., Davidson, C., Koper, O.,
Zaikovski, V., Volodin, A., Rieker, T., & Klabunde, K.
J. (2000). Consolidation of metal oxide nanocrystals. Re-
active pellets with controllable pore structure that repre-
sent a new family of porous, inorganic materials. Journal
of the American Chemical Society, 122, 4921–4925. DOI:
10.1021/ja994383g.
Roopan, S. M., & Khan, F. R. N. (2009). Synthesis, antioxi-
dant, hemolytic and cytotoxicity activity of AB ring core of
mappicine. ARKIVOC, xiii, 161–169.
Roopan, S. M., Khan, F. R. N., & Mandal, B. K. (2010). Fe nano
particles mediated C–N bond forming reaction: Regioselec-
tive synthesis of 3-[(2-chloroquinolin-3-yl)methyl]pyrimidin-
4(3H )ones. Tetrahedron Letters, 51, 2309–2311. DOI: 10.
1016/j.tetlet.2010.02.128.
Acknowledgements. The authors gratefully acknowledge fi-
nancial support from the Department of Science and Technol-
ogy, Government of India (Grant No. SR/FTP/CS-99/2006).
The authors are also thankful to the VIT University manage-
ment for their generous support and facilities. We also ac-
knowledge SAIF, IIT Madras, Chennai, for providing NMR and
MS facilities.
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