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Green Chemistry
Page 5 of 6
DOI: 10.1039/C5GC01884F
Journal Name
COMMUNICATION
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A. N. Campbell and S. S. Stahl, Acc. Chem. Res., 2012, 45,
851.
At last, we attempted to reuse the PEG-600. After
completion of the reaction, PEG was recovered and subjected
to another run, affording the product in almost same yield.
This process was repeated three more times, affording the
product in excellent yields (Table 4). It is important to note
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Angew. Chem., Int. Ed., 2006, 45, 7896; (d) A. Corma and H.
Garcia, Chem. Soc. Rev., 2008, 37, 2096; (e) Y. Chen, D. M. Ho
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Ackermann and L. T. Kaspar, J. Org. Chem., 2007, 72, 6149;
(g) For a review, see : Z. Shi, C. Zhang, C. Tanga and N. Jiao,
Chem. Soc. Rev., 2012, 41, 3381.
that weight loss 10% of PEG was observed for every run due
~
to handling loss. The simple experimental and ease of product
separation combined with the easy recovery and reuse of PEG
is expected to contribute to the development of a green
methodology for the synthesis of 1,3,5-triazines.
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C. Reichardt and T. Welton, Solvents and Solvent Effects in
Organic Chemistry, WILEY-VCH Verlag GmbH & Co. KGaA,
Weinheim, 2011.
Table 4 Recyclability study of PEG
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Chem., 2014, 16, 4223; (f) For a review, see : M. B. Gawande,
V. D. B. Bonifa´cio, R. Luque, P. S. Brancoa and R. S. Varma,
Chem. Soc. Rev., 2013, 42, 5522.
Run
Yieldb (%)
1
2
3
95
95
94
a
Reaction conditions: benzylamine (1, 0.5 mmol), amidine hydrochlorides
(2, 1.0 mmol), Cs2CO3 (1.0 mmol), PEG (2.5 mL) for 3 h. b Isolated Yield.
Conclusions
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Wagh, B.M. Bhanage, Green Chem., 2015, 17, 4446; (f) K.V.
In conclusion, a highly efficient, transition-metal free synthesis
of 1,3,5-triazines has been developed by employing molecular
oxygen as a green oxidant in PEG-600. The use of molecular
oxygen and non toxic as solvent PEG-600 has made this
protocol economical, environmentally benign and potentially
viable for commercial and academic applications. Various
1,3,5-triazines were synthesized in good to excellent yields.
The developed methodology is suitable for the gram-scale
synthesis, owing to its simple non-aqueous work up, shorter
reaction time and higher yield. This protocol offers an
excellent chance to avoid the toxic solvents, catalysts and use
of natural resources than previous reports. Noteworthy, for
the first time we have demonstrated the synthesis of imines
form N-mono and N,N-di substituted benzylamines. Moreover,
the after extraction of with ether, PEG-600 was recovered and
could be reused up to three consecutive cycles.
Wagh, B.M. Bhanage, RSC Adv., 2014,
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Acknowledgment
The author (ART) is greatly thankful to UGC (University Grant
Commission) India, New Delhi for providing BSR fellowship.
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