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http://dx.doi.org/10.1016/j.jiec.2018.08.010

Supramolecular aminocatalysis via inclusion complex: Amino-doped β-cyclodextrin as an efficient supramolecular catalyst for the synthesis of chromeno pyrimido[1,2-b]indazol in water  

Shinde, Vijay Vilas (Institute for Ubiquitous Information Technology and Applications (UBITA) & Center for Biotechnology Research in UBITA (CBRU), Konkuk University)
Jeong, Daham (Institute for Ubiquitous Information Technology and Applications (UBITA) & Center for Biotechnology Research in UBITA (CBRU), Konkuk University)
Jung, Seunho (Institute for Ubiquitous Information Technology and Applications (UBITA) & Center for Biotechnology Research in UBITA (CBRU), Konkuk University)
Publication Information
Journal of Industrial and Engineering Chemistry / v.68, no., 2018 , pp. 6-13 More about this Journal
Abstract
Well-modified amino-appended ${\beta}$-cyclodextrin ($AA-{\beta}-CD$) with an amino group at the primary face of the ${\beta}-CD$ was synthesized and used in the catalytic synthesis of chromeno pyrimido[1,2-b]indazol as supramolecular catalysts in water for the first time. $AA-{\beta}-CD$ was characterized by FT-IR, NMR, MALDI-TOF mass spectrometry, and SEM analysis. A possible reaction mechanism featuring molecular complexation was suggested based on 2D NMR (ROESY) spectroscopy, FE-SEM, DSC, and FT-IR. Advantages such as operational simplicity, recyclability of the catalysts, and accessibility in aqueous medium render this protocol eco-friendly.
Keywords
Mono-6-deoxy-6-amino-${\beta}$-cyclodextrin; Amino-appended supramolecular catalyst; Poly heterocycles; One-pot synthesis; 2D ROESY NMR;
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1 (c) S. Ravi Kanth, G. Venkat Reddy, K.P. Hara Kishore, S. Rao, B. Narsaiah, U.S.N. Murthy, Eur. J. Med. Chem. 41 (2006) 1011   DOI
2 (d) P.V.S. Salvatore, L.M. Marino, J. Heteroatom Chem. 10 (1973) 261   DOI
3 (e) R. Hans, M.A. Peiren, M. Roert, Chem. Ber. 105 (1972) 794   DOI
4 (f) L. Li, H. Xu, L. Dai, J. Xi, L. Gao, L. Rong, Tetrahedron 73 (2017) 5358   DOI
5 (g) G. Rahimzadeh, S. Bahadorikhalili, E. Kianmehr, M. Mahdavi, Mol. Divers. 21 (2017) 597   DOI
6 (h) A.M. Jadhav, S.G. Balwe, K.T. Lim, Y.T. Jeong, Tetrahedron 73 (2017) 2806.   DOI
7 (a) V.V. Shinde, Y.S. Jeong, Y.T. Jeong, Mol. Divers 19 (2015) 367   DOI
8 (b) H.Y. Wang, X.C. Liu, X. Feng, Z.B. Huang, D.Q. Shi, Green Chem. 15 (2013) 3307   DOI
9 (c) J.D. Hu, C.P. Cao, W. Lin, M.H. Hu, Z.B. Huang, D.Q. Shi, J. Org. Chem. 79 (2014) 7935.   DOI
10 (a) M. Lu, D. Zhu, Y. Lu, B. Hou, B. Tan, G. Zhong, Angew. Chem. Int. Ed. 47 (2008) 10187   DOI
11 D. French, Adv. Carbohydr. Chem. 12 (1957) 189.
12 (b) J.W. Yang, H.M.T. Fonseca, B. List, J. Am. Chem. Soc. 127 (2005) 15036   DOI
13 (c) V.V. Shinde, Y.T. Jeong, Tetrahedron 72 (2016) 4377.   DOI
14 M. Raynal, P. Ballester, A. Vidal-Ferran, P.W. van Leeuwen, Chem. Soc. Rev. 43 (2014) 1734.   DOI
15 J. Szeitli, Cyclodextrin Technology, Klwner Academic Publication, Doedracht, 1988.
16 J. Zhang, P.X. Ma, Adv. Drug Deliv. Rev. 65 (2013) 1215.   DOI
17 K. Kuppusamy, S. Palaniswamy, P. Kasi, Org. Lett. 12 (2010) 18.
18 K. Kuppusamy, S. Palaniswamy, P. Kasi, J. Org. Chem. 78 (2013) 744.   DOI
19 H. Shen, H. Ji, Carbohydr. Res. 49 (2012) 354.
20 S. Palaniswamy, P. Kasi, J. Org. Chem. 73 (2008) 9121.   DOI
21 V.V. Shinde, D. Jeong, S.W. Joo, E. Cho, S. Jung, Catal. Commun. 103 (2018) 83.   DOI
22 I.A. Azath, P. Puthiaraj, K. Pitchumani, ACS Sustain. Chem. Eng. 1 (2013) 174.   DOI
23 Y. Ren, B. Yang, X. Liao, Catal. Sci. Technol. 6 (2016) 4283.   DOI
24 H.S. Byun, N. Zhong, R. Bittman, Organic Synth. 77 (2000) 225.   DOI
25 R. Patel, M. Patel, Drug Discov. Ther. 4 (2010) 442.
26 D.R. de Araujo, S.S. Tsuneda, C.M.S. Cereda, G.F.F. Del, P.S.C. Preté, S.A. Fernandes, E. de Paula, Eur. J. Pharm. Sci. 33 (2008) 60.   DOI
27 T. Yakaiah, B.P.V. Lingaiah, B. Narsaiah, K.P. Kumar, U.S.N. Murthy, Eur. J. Med. Chem. 43 (2008) 341.   DOI
28 A. Kamphorst, I.M. de Sa, A. Faria, R. Sinisterra, Eur. J. Pharm. Biopharm. 57 (2004) 199.   DOI
29 (a) M. Thangadurai, S. Minu, S. Wakode, Med. Chem. Res. 21 (2012) 1509   DOI
30 M.C. Venuti, R. Jones, J.J. Bruno, J. Med. Chem. 30 (1987) 303.   DOI
31 R.D. Amici, A.K.M. Matteo, S.B.A. Vetti, PCT Int. Appl. WO 0328, 720 (2003) 132 pp. (Eng) (C.A.138: 304278t).
32 (b) B.J. Whilock, S.H. Lipton, F.M. Strong, J. Org. Chem. (1965) 115.
33 N. Conception, M. Patrick, F. Thompson, M.T. Fabienne, B. Eric, W. Sylvie, C. Cecile, PCT Int. Appl. WO 0311, 833 (2003) 188 pp. (Fr) (C.A. 138: 153529x).
34 M. Pedro, A. Antonio, V. Maria, V. Vinader, Tetrahedron Lett. 30 (1989) 6237.   DOI
35 (a) R.J. Griffin, P.R. Lowe, J. Chem. Soc. Perkin Trans. 1 (1992) 1811
36 N. Conception, M. Patrick, F. Thompson, M.T. Fabienne, B. Eric, W. Sylvie, C. Cecile, PCT Int. Appl. WO 0311, 833 (2003) 188 pp. (Fr) (C.A. 138: 153529x).
37 (a) T. Yakaiah, C. Kurumurthy, B.P.V. Lingaiah, B. Narsaiah, R. Pamanji, L.R. Velatooru, J.V. Rao, S. Gururaj, T. Parthasarathy, B. Sridhar, Med. Chem. Res. 21 (2012) 4261   DOI
38 (b) D. Matraie, G. Venkat Reddy, V.V.V.N.S. Ramarao, S.B. Ravikanth Narsaiah, P. S. Rao, K. Ravikumar, B. Sridhar, Tetrahedron 16 (2005) 3999