Highly Monodispersed PEG-stabilized Ni Nanoparticles: Proficient Catalyst for the Synthesis of Biologically Important Spiropyrans
Jitender M. Khurana A B and Sneha Yadav A
+ Author Affiliations
- Author Affiliations
A Department of Chemistry, University of Delhi, Delhi 110007, India.
B Corresponding author. Email: jmkhurana1@yahoo.co.in
Australian Journal of Chemistry 65(3) 314-319 https://doi.org/10.1071/CH11444
Submitted: 22 November 2011 Accepted: 17 January 2012 Published: 24 February 2012
Abstract
A convenient and efficient synthesis of biologically and pharmacologically important spiropyrans from the condensation of malononitrile, 1,3-dicarbonyl compounds and ninhydrin/acenaphthequinone/isatin has been reported using recyclable heterogeneous polyethylene glycol (PEG)-stabilized Ni nanoparticles in ethylene glycol. This new protocol affords products in high yields and less reaction time.
References
[1] K. A. Parker, A. Dermatakis, J. Org. Chem. 1997, 62, 4164.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXjsVSrtb8%3D&md5=8fda1ba1f991ad74fe8676bb05c2e339CAS |
[2] M. J. Kukla, H. J. Breslin, C. J. Diamond, P. A. J. Janssen, J. Med. Chem. 1991, 34, 3187.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXmtlaiu7s%3D&md5=ee577057a55141c138b9d557ab008290CAS |
[3] B. Le Bourdonnec, R. T. Windh, L. K. Leister, Q. J. Zhou, C. W. Ajello, M. Gu, G. H. Chu, P. A. Tuthill, W. M. Barker, M. Koblish, D. D. Wiant, T. M. Graczyk, S. Belanger, J. A. Cassel, M. S. Feschenko, B. L. Brogdon, S. A. Smith, M. J. Derelanko, S. Kutz, P. J. Little, R. N. DeHaven, D. L. H. DeHaven, R. E. Dolle, J. Med. Chem. 2009, 52, 5685.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtVWkurvP&md5=ba21c89a727aad4313a93bcb1e60ed1bCAS |
[4] B. Schaudel, C. Guermeur, C. Sanchez, K. Nakatani, J. A. Delaire, Mater. J. Chem. 1997, 7, 61.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXmtlyqsw%3D%3D&md5=104a808195719807698fe1ab6713fa00CAS |
[5] V. Glover, J. M. Halket, P. J. Watkins, A. Clow, B. L. Goodwin, M. Sandler, J. Neurochem. 1988, 51, 656.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXlt1KgsLw%3D&md5=d21c511f6f130b2347b5ce2a5ee7c16cCAS |
[6] R. Kumar, R. C. Bansal, A. Mahmood, Biog. Amines 1993, 9, 281.
| 1:CAS:528:DyaK3sXkvVGqs7g%3D&md5=1e16f3c47d09f77fb1d0201cf651b394CAS |
[7] A. E. Medvedev, A. Clow, M. Sandler, V. Glover, Biochem. Pharmacol. 1996, 52, 385.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28Xkt1OgtLk%3D&md5=8921e243133381bad4cf4062b0ae6617CAS |
[8] (a) S. K. Bhattacharya, S. K. Mitra, S. B. Acharya, J. Psychopharmacol. 1991, 5, 202.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXmslWntLk%3D&md5=defc1c68300f4d15b0e7340e3a58a27aCAS |
(b) S. K. Bhattacharya, V. Glover, I. McIntyre, G. Oxenkrug, M. Sandler, Neurosci. Lett. 1988, 92, 218.
| Crossref | GoogleScholarGoogle Scholar |
[9] A. Dandia, R. Singh, S. Khaturia, C. Merienne, G. Morgant, A. Loupy, Bioorg. Med. Chem. 2006, 14, 2409.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhsFKqt74%3D&md5=8c34b8a478839e46d9d48b5a992eb6b0CAS |
[10] P. R. Sebahar, R. M. Williams, J. Am. Chem. Soc. 2000, 122, 5666.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXjtlygtrk%3D&md5=dcd2f68f893d5537646c2f568c627dafCAS |
[11] S. Edmondson, S. J. Danishefsky, L. Sepp-Lorenzinol, N. Rosen, J. Am. Chem. Soc. 1999, 121, 2147.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXht12gsL8%3D&md5=8a16a2659519eb95cafe8bd1cf5302f4CAS |
[12] M. M. Joullie, T. R. Thompson, N. H. Nemeroff, Tetrahedron 1991, 47, 8791. and references cited therein
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK38XotlarsA%3D%3D&md5=183987d6b656d04b4bf32032194b663aCAS |
[13] (a) R. M. Shaker, A. F. Mahmoud, F. F. Abdel-Latif, J. Chin. Chem. Soc 2005, 52, 563.
| 1:CAS:528:DC%2BD2MXhtVSktrvO&md5=944f6da757e61eee9c0aeedd51588d18CAS |
(b) Y. He, H. Guo, J. Tian, J. Chem. Res. 2011, 35, 528.
| Crossref | GoogleScholarGoogle Scholar |
[14] (a) Y. Li, H. Chen, C. Shi, D. Shi, S. Ji, J. Comb. Chem. 2010, 12, 231.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXnvFWlsg%3D%3D&md5=d2a98b2439770cfb8d6da48ae703c173CAS |
(b) M. N. Elinson, Electrochim. Acta 2008, 53, 8346.
| Crossref | GoogleScholarGoogle Scholar |
[15] A. R. Karimi, F. Sedaghatpour, Synthesis 2010, 10, 1731.
| Crossref | GoogleScholarGoogle Scholar |
[16] M. Saeedi, M. M. Heravi, Y. S. Beheshtiha, H. A. Oskooie, Tetrahedron 2010, 66, 5345.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXnvFSqurg%3D&md5=e3255ed1ebb721910db0d8cb2b6b789bCAS |
[17] (a) R. Ghahremanzadeh, J. Heterocycl. Chem. 2010, 47, 46.
| 1:CAS:528:DC%2BC3cXht12ksL8%3D&md5=cf4cb57df1d01a6805298bbcb5f9a8a5CAS |
(b) R. Ghahremanzadeh, J. Heterocycl. Chem. 2009, 46, 1266.
| Crossref | GoogleScholarGoogle Scholar |
[18] F. Alonso, I. Osante, M. Yus, Synlett 2006, 3017.
| 1:CAS:528:DC%2BD28Xht1KgsrvP&md5=7fe7bb76a678acea40dd8fc9affe8f8eCAS |
[19] J. Park, E. Kang, S. U. Son, H. M. Park, M. K. Lee, J. Kim, K. W. Kim, H.-J. Noh, J.-H. Park, C. J. Bae, J.-G. Park, T. Hyeon, Adv. Mater. (Deerfield Beach Fla.) 2005, 17, 429.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXitl2rsrs%3D&md5=cb7d0213e7633dc4cb49a09b9fe2fcd7CAS |
[20] W. Zhang, H. Qi, L. Li, X. Wang, J. Chen, K. Peng, Z. Wang, Green Chem. 2009, 11, 1194.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXpsFSitLo%3D&md5=3f0afe024af100c9c56405cbf32b1d51CAS |
[21] B. H. Lipshutz, P. A. Blomgren, J. Am. Chem. Soc. 1999, 121, 5819.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXjsFajsbg%3D&md5=a4fd8282b6525791b235f96475d131b1CAS |
[22] B. H. Lipshutz, T. Tomioka, P. A. Blomgren, J. A. Sclafani, Inorg. Chim. Acta 1999, 296, 164.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXnvFKitbs%3D&md5=49ccfb41d0db9d71665360d2c014120aCAS |
[23] S. Martínez, M. Moreno-Mañas, A. Vallribera, U. Schubert, A. Roig, E. Molins, N. J. Chem. 2006, 30, 1093.
| Crossref | GoogleScholarGoogle Scholar |
[24] F. Alonso, P. Riente, M. Yus, Synlett 2009, 10, 1579.
| Crossref | GoogleScholarGoogle Scholar |
[25] F. Alonso, P. Riente, M. Yus, Eur. J. Org. Chem. 2008, 29, 4908.
| Crossref | GoogleScholarGoogle Scholar |
[26] J. M. Khurana, K. Vij, Catal. Lett. 2010, 138, 104.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXntVertL8%3D&md5=beacdecab2f39c16c1e14ea71d14f11fCAS |
[27] J. M. Khurana, K. Sneha, K. Vij, Synth. Commun. in press
[28] J. M. Khurana, K. Vij, Tetrahedron Lett. 2011, 52, 3666.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXnsVClsLY%3D&md5=dbcedb17af15541356743c60840b9bdeCAS |
