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COMMUNICATION
Journal Name
Offers
a
DOI: 10.1039/C6RA13712A
reusable catalyst for the preparation of N-containing
poly heterocyclic compounds using commercially
available reagents
The synthetic strategy follow the formation of two new
C-N bonds and a C-O bond by using two simple starting
materials
Target molecules were achieved without formation of
any by-products in the reaction mixture
Currently, our group is involved in exploring the additional
aspects of developed catalytic system.
Acknowledgment
Special thanks to the Dr.Ajaybabu Naidu for his valuable
suggestions during the course of this work. Dr. S. R. Reddy
thanks to the (DST-SERB-SR/FT/CS-93/2011), Govt. of India for
providing the fund under the young scientist Scheme and we
also thank the SIF-VIT-DST-FIST for NMR and GC-MS
facilitiesand RGEMS grant
Scheme 2. Proposed reaction mechanism of copper catalyzed tandem cyclization
Supplementary material is available for this article
Notes and references
Scheme 3. Synthesis of enol lactone II
1
(a) A. Diéguez‐Vázquez, C. C. Tzschucke, W. Y. Lam and S. V.
Ley, Angew. Chem. Int. Ed., 2008, 47, 209-212; (b) D. S. H. Chan,
H. M. Lee, F. Yang, C. M. Che, C. C. Wong,R. Abagyan, C. H. Leung
and D. L. Ma, Angew. Chem., 2010, 122, 2922-2926;(c) M. Shiri,
Chem. Rev., 2012, 112, 3508-3549; (d) G. Wu, W. Yin, H. C. Shen
and Y. Huang, Green Chem., 2012, 14, 580-585; (e) Y. Miura, N.
Hayashi, S. Yokoshima and T. Fukuyama, J. Am. Chem. Soc.,
2
2
012, 134, 11995-11997.
(a) Y. Murata, D. Yamashita, K. Kitahara, Y. Minasako and A.
Scheme4. Synthesis of 4a, using II and 1a, with Cu(OAc)
2
.H
2
O
Nakazaki, Angew. Chem., 2009, 121, 1428-1431; (b) E.
Gromachevskaya, F. Kvitkovskii, T. Kosulina and V. Kul'nevich,
Chem.Heterocycl.Compd., 2003, 39, 137-155.
Furthermore, the recyclability and reusability of the developed
catalyst and solvent system was tested. It was found that the
catalyst as well as solvent, ([bmim]OTf) is recyclable and
3
(a) F. Dumitrascu and M. M. Popa, Arkivoc., 2014, 1, 428-452;
(
b) H. Huang, Y. Zhou and H. Liu, Beilstein J. Org. Chem., 2011,
7,
8
97-936; (c)T. J. Sindhu, D. A. Sonia, V. Girly, M. Chandran, A. R.
reusable up to five runs without any significant loss in the Bhat, K. H. Krishnakumar. International Journal of Pharma
Sciences and Research. 2013,
4, 134-143. (d) F. Touzeau, A.
catalytic activity. The product was obtained in excellent yields
upto five cycles, and results were summarized in table 3.
Arrault, G. Guillaumet, E. Scalbert, B. Pfeiffer, M.-C. Rettori, P.
Renard and J.-Y.Mérour, J. Med. Chem., 2003, 46, 1962-1979.
1
5
4
(a) A. Padwa, Pure Appl. Chem., 2004, 76, 1933-1952; (b) M.
Table 3: Recyclability experiments for catalyst and Ionic liquid
Ihara, Arkivoc., 2006, 7, 416-438.
a
5 (a) Y. Zhou, J. Li, X. Ji, W. Zhou, X. Zhang, W. Qian, H. Jiang and
H. Liu, J. Org. Chem., 2011, 76, 1239-1249; (b) N. Patil, A.
Mutyala and P. Lakshmi, J. Org. Chem., 2010, 75, 5963-5975; (c)
T. Yang, L. Campbell and D. J. Dixon, J. Am. Chem. Soc., 2007,
Run
Time(h)
Yield
92
90
90
86
1
8
8
8
8
8
2
3
4
5
1
29, 12070-12071; (d)N. T. Patil, P. G. Lakshmi, B. Sridhar, S.
Patra, M. Pal Bhadra and C. R. Patra, Eur. J. Org. Chem., 2012,
012, 1790-1799; (e) Y. Zhou, X. Ji, G. Liu, D. Zhang, L. Zhao, H.
86
2
Note: Conditions,Substrate (0.5 mmol) 2a, (1.25 mmol), catalyst (5 mol%, 5 mg),
Jiang and H. Liu, Adv. Synth. Catal., 2010, 352, 1711-1717; (f) Y.
Zhou, Y. Zhai, X. Ji, G. Liu, E. Feng, D. Ye, L. Zhao, H. Jiang and H.
Liu, Adv. Synth. Catal., 2010, 352, 373-378.
[
a]
[
bmim]OTf, 0.5 mL, 100 ᵒC ; Isolated yields
Conclusions
6
(a) M. T. Richers, M. Breugst, A. Y. Platonova, A. Ullrich, A.
Dieckmann, K. Houk and D. Seidel, J. Am. Chem. Soc., 2014, 136
,
In Summary, we report a facile method for the synthesis of
pyrrolo-/pyrido[2,1-b]benzo[d][1,3]oxazin-1-ones
6
2
123-6135; (b) F. Kienzle, Tetrahedron Lett., 1983, 24, 2213-
216; (c) X.-J. Shang and Z.-Q. Liu, Tetrahedron Lett., 2015, 56
via
Cu
,
catalysed tandem cyclization in green reaction medium. 482-484; (d) A. Jha, A. B. Naidu and A. M. Abdelkhalik, Org
Biomol Chem., 2013, 11, 7559- 7565.
Advantages of this developed method are:
4
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