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

Vijay Vilas Shinde; Daham Jeong; Seunho Jung

Journal of Industrial and Engineering Chemistry, Vol.68, 6-13, December, 2018

DOI10.1016/j.jiec.2018.08.010 Export Citation

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

Vijay Vilas Shinde¹, Daham Jeong^{1, 2}, and Seunho Jung^{1, 2, †}

¹Institute for Ubiquitous Information Technology and Applications (UBITA) & Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 143-701, South Korea
²Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, Seoul 143-701, South Korea

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Well-modified amino-appended β-cyclodextrin (AA-β-CD) with an amino group at the primary face of the β-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-β-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-β-cyclodextrin;Amino-appended supramolecular catalyst;Poly heterocycles;One-pot synthesis;2D ROESY NMR

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Shinde VV, Jeong D, Joo SW, Cho E, Jung S, Catal. Commun., 103, 83 (2018)
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[Referenced By]

[1] (a)Thangadurai M, Minu S, Wakode S, Med. Chem. Res. 21, 1509 (2012). (b)Venuti MC, Jones R, Bruno JJ, Med J. Chem. 30, 303 (1987).

[2] Yakaiah T, Lingaiah BPV, Narsaiah B, Kumar KP, Murthy USN, Eur. J. Med. Chem., 43, 341 (2008)

[3] Amici RD, Matteo AKM, Vetti SBA, PCT Int. Appl. WO 0328, 720 pp.132 (2003).

[4] Conception N, Patrick M, Thompson F, Fabienne MT, Eric B, Sylvie W, Cecile C, PCT Int. Appl. WO 0311, 833, pp.188 (2003).

[5] Pedro M, Antonio A, Maria V, Vinader V, Tetrahedron Lett., 30, 6237 (1989)

[6] (a)Griffin RJ, Lowe PR, J. Chem. Soc. Perkin Trans. 1, 1811 (1992). (b)Whilock BJ, Lipton SH, Strong FM, J. Org. Chem., 115 (1965).

[7] Conception N, Patrick M, Thompson F, Fabienne MT, Eric B, Sylvie W, Cecile C, PCT Int. Appl. WO 0311, 833 pp. 188 (2003).

[8] (a)Yakaiah T, Kurumurthy C, Lingaiah BPV, Narsaiah B, Pamanji R, Velatooru LR, Rao JV, Gururaj S, Parthasarathy T, Sridhar B, Med. Chem. Res. 21, 4261 (2012). (b)Matraie D, Reddy GV, Ramarao VVVNS, Narsaiah SBR, Rao PS, Ravikumar K, Sridhar B, Tetrahedron, 16, 3999 (2005). (c)Kanth SR, Reddy GV, Kishore KPH, Rao S, Narsaiah B, Murthy USN, Eur. J. Med. Chem., 41, 1011 (2006). (d)Salvatore PVS, Marino LM, J. Heteroatom Chem., 10, 261 (1973). (e)Hans R, Peiren MA, Roert M, Chem. Ber., 105, 794 (1972). (f) Li L, Xu H, Dai L, Xi J, Gao L, Rong L, Tetrahedron, 73, 5358 (2017).(g)Rahimzadeh G, Bahadorikhalili S, Kianmehr E, Mahdavi M, Mol. Divers., 21, 597 (2017). (h)Jadhav AM, Balwe SG, Lim KT, Jeong YT, Tetrahedron, 73, 2806 (2017).

[9] (a)Shinde VV, Jeong YS, Jeong YT, Mol. Divers, 19, 367 (2015). (b)Wang HY, Liu XC, Feng X, Huang ZB, Shi DQ, Green Chem., 15, 3307 (2013). (c)Hu JD, Cao CP, Lin W, Hu MH, Huang ZB, Shi DQ, J. Org. Chem., 79, 7935 (2014).

[10] (a)Lu M, Zhu D, Lu Y, Hou B, Tan B, Zhong G, Angew. Chem. Int. Ed., 47, 1087 (2008).(b)Yang JW, Fonseca HMT, List B, J. Am. Chem. Soc., 127, 15036 (2005). (c)Shinde VV, Jeong YT, Tetrahedron, 72, 4377 (2016).

[11] Raynal M, Ballester P, Vidal-Ferran A, van Leeuwen PW, Chem. Soc. Rev., 43, 1734 (2014)

[12] French D, Adv. Carbohydr. Chem., 12, 189 (1957)

[13] Szeitli J, Cyclodextrin Technology, Klwner Academic Publication, Doedracht, 1988.

[14] Zhang J, Ma PX, Adv. Drug Deliv. Rev., 65, 1215 (2013)

[15] Kuppusamy K, Palaniswamy S, Kasi P, Org. Lett., 12, 18 (2010)

[16] Kuppusamy K, Palaniswamy S, Kasi P, J. Org. Chem., 78, 744 (2013)

[17] Shen H, Ji H, Carbohydr. Res., 49, 354 (2012)

[18] Palaniswamy S, Kasi P, J. Org. Chem., 73, 9121 (2008)

[19] Shinde VV, Jeong D, Joo SW, Cho E, Jung S, Catal. Commun., 103, 83 (2018)

[20] Azath IA, Puthiaraj P, Pitchumani K, ACS Sustain. Chem. Eng., 1, 174 (2013)

[21] Ren Y, Yang B, Liao X, Catal. Sci. Technol., 6, 4283 (2016)

[22] Byun HS, Zhong N, Bittman R, Organic Synth., 77, 225 (2000)

[23] Patel R, Patel M, Drug Discov. Ther., 4, 442 (2010)

[24] de Araujo DR, Tsuneda SS, Cereda CMS, Del GFF, Prete PSC, Fernandes SA, de Paula E, Eur. J. Pharm. Sci., 33, 60 (2008)

[25] Kamphorst A, de Sa IM, Faria A, Sinisterra R, Eur. J. Pharm. Biopharm., 57, 199 (2004)