Multicomponent One-pot Green Synthesis of 1-Amidoalkyl-2-naphthols Promoted by p-Nitrobenzoic Acid Under Solvent-free Condition

Tiangang Li; Xing Zhai; Dharamveer Singh; Rajesh K. Singh; Xuegong Xu

doi:10.14233/ajchem.2014.16707

Issue

Vol. 26 No. 16 (2014): Vol 26 Issue 16

Issue Published : July 28, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Multicomponent One-pot Green Synthesis of 1-Amidoalkyl-2-naphthols Promoted by p-Nitrobenzoic Acid Under Solvent-free Condition

https://doi.org/10.14233/ajchem.2014.16707

Tiangang Li

Beijing University of Chinese Medicine, Beijing 100029, P.R. China;Both authors contributed equally to this paper.

Xing Zhai

Beijing University of Chinese Medicine, Beijing 100029, P.R. China;Both authors contributed equally to this paper.

Dharamveer Singh

Department of Pharmaceutical Chemistry, Shivalik College of Pharmacy, Nangal-140 126, India

Rajesh K. Singh

Department of Pharmaceutical Chemistry, Shivalik College of Pharmacy, Nangal-140 126, India

Xuegong Xu

Zhengzhou Traditional Chinese Medicine Hospital, Zhengzhou, P.R. China

Corresponding Author(s) : Rajesh K. Singh

rksingh244@gmail.com

Asian Journal of Chemistry, Vol. 26 No. 16 (2014): Vol 26 Issue 16
Article Published : August 4, 2014

Abstract

A series of sixteen 1-amidoalkyl-2-naphthols derivatives were synthesized by one-pot multicomponent condensation reaction of b-naphthol with various aromatic aldehydes and amides under thermal (hot plate and oil bath) and microwave irradiation techniques promoted by p-nitrobenzoic acid and the corresponding products were obtained in good to excellent yield (82-92 %) under solvent-free condition.

Keywords

1-Amidoalkyl-2-naphthol p-Nitrobenzoic acid Multicomponent one-pot reaction Microwave irradiation Solvent-free

Li, T., Zhai, X., Singh, D., K. Singh, R., & Xu, X. (2014). Multicomponent One-pot Green Synthesis of 1-Amidoalkyl-2-naphthols Promoted by p-Nitrobenzoic Acid Under Solvent-free Condition. Asian Journal of Chemistry, 26(16), 5207–5211. https://doi.org/10.14233/ajchem.2014.16707

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References

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I. Szatmari and F. Fulop, Curr Org Synth, 1, 155 (2004); doi:10.2174/1570179043485402.
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(a) S.B. Patil, P.R. Singh, M.P. Surpur and S.D. Samant, Ultrason. Sonochem., 14, 515 (2007); doi:10.1016/j.ultsonch.2006.09.006; (b) R.R. Nagawade and D.B. Shinde, Chin. J. Chem., 25, 1710 (2007); doi:10.1002/cjoc.200790316.
R. Ghorbani-Vaghei and S.M. Malaekehpour, Cent. Eur. J. Chem., 8, 1086 (2010); doi:10.2478/s11532-010-0077-0.
(a) A. Kumar, M.S. Rao, I. Ahmad and B. Khungar, Can. J. Chem., 87, 714 (2009); doi:10.1139/V09-049; (b) H. Khabazzadeh, K. Saidi and N. Seyedi, J. Chem. Sci., 121, 429 (2009); doi:10.1007/s12039-009-0050-7; (c) A.R. Hajipour, F. Ghayeb, N. Sheikhan and A.E. Ruoho, Tetrahedron Lett., 50, 5649 (2009); doi:10.1016/j.tetlet.2009.07.116. (d) S.B. Sapkal, K.F. Shelke, B.R. Madje, B.B. Shingate and M.S. Shingare, Bull. Korean Chem. Soc., 30, 2887 (2009); doi:10.5012/bkcs.2009.30.12.2887; (e) T.T. She, Z.L. Liu and K. Gong, Chinese J. Appl. Chem., 27, 778 (2010).
(a) P.T. Anastas and J.C. Warner, Green Chemistry: Theory and Practice; Oxford University Press, Oxford, UK (1998); (b) P.T. Anastas and T. Williamson, Green Chemistry, Frontiers in Benign Chemical Synthesis and Process; Oxford University Press, Oxford, UK (1998).
(a) R. Duvedi and R.K. Singh, Asian J. Chem, 24, 5665 (2012); (b) S. Sharma, D.N. Prasad and R.K. Singh, J. Chem. Pharm. Res, 3, 382 (2011); (c) A. Sandhar, D.N. Prasad and R.K. Singh, Indian J. Heterocycl. Chem., 21, 369 (2012) (c) A. Sandhar, D.N. Prasad, A. Kapoor and R.K. Singh, Curr. Res. Chem, 4, 68 (2012); (d) S. Malik, S. Sharma and R.K. Singh, Asian J. Chem., 24, 5669 (2012); (e) P. Kaur, H. Sharma, R. Rana, D.N. Prasad and R.K. Singh, Asian J. Chem, 24, 5649 (2012); (f) A. Sandhar and R.K. Singh, Asian J. Chem, 24, 5643 (2012); (g) A. Sandhar and R.K. Singh, Chem. Sci. Trans., 2(S1), 176 (2012); doi:10.7598/cst2013.315.; (h) R.K. Singh, B. Singh, R. Duvedi and S. Kumar, Res. Chem. Intermed., (2014); doi:10.1007/s11164-013-1513-5.
R. Varala, R. Enugala and S.R. Adapa, J. Braz. Chem. Soc., 18, 291 (2007); doi:10.1590/S0103-50532007000200008.

References

A.Y. Shen, C.T. Tsai and C.L. Chen, Eur. J. Med. Chem., 34, 877 (1999); doi:10.1016/S0223-5234(99)00204-4.

I. Szatmari and F. Fulop, Curr Org Synth, 1, 155 (2004); doi:10.2174/1570179043485402.

M. Damodiran, N. Panneer Selvam and P.T. Perumal, Tetrahedron Lett., 50, 5474 (2009); doi:10.1016/j.tetlet.2009.07.051.

A.H. Kategaonkar, S.S. Sonar, K.F. Shelke, B.B. Shingate and M.S. Shingare, Org. Commun., 3, 1 (2010).

Y. Kusakabe, J. Nagatsu, M. Shibuya, O. Kawaguchi, C. Hirose and S. Shirato, J. Antibiot., 25, 44 (1972); doi:10.7164/antibiotics.25.44.

J.B. Chylińska, T. Urbański and M. Mordarski, J. Med. Chem., 6, 484 (1963); doi:10.1021/jm00341a004.

J.L. Peglion, J. Vian, B. Goument, N. Despaux, V. Audinot and M.J. Millan, Bioorg. Med. Chem. Lett., 7, 881 (1997); doi:10.1016/S0960-894X(97)00126-1.

H. Ren, S. Grady, D. Gamenara, H. Heinzen, P. Moyna, S. Croft, H. Kendrick, V. Yardley and G. Moyna, Bioorg. Med. Chem. Lett., 11, 1851 (2001); doi:10.1016/S0960-894X(01)00308-0.

F. Benedini, G. Bertolini, R. Cereda, G. Doná, G. Gromo, S. Levi, J. Mizrahi and A. Sala, J. Med. Chem., 38, 130 (1995); doi:10.1021/jm00001a018.

R.D. Clark, J.M. Caroon, A.F. Kluge, D.B. Repke, A.P. Roszkowski, A.M. Strosberg, S. Baker, S.M. Bitter and M.D. Okada, J. Med. Chem., 26, 657 (1983); doi:10.1021/jm00359a007.

J.B. Chylińska, M. Janowiec and T. Urbański, Br. J. Pharmacol., 43, 649 (1971); doi:10.1111/j.1476-5381.1971.tb07194.x.

S. Knapp, Chem. Rev., 95, 1859 (1995); doi:10.1021/cr00038a006.

S.M. Vrouenraets, W.F. Wit, J. Tongeren and J.M. Lange, Expert Opin. Pharmacother., 8, 851 (2007); doi:10.1517/14656566.8.6.851.

M. Anary-Abbasinejad, A. Hassanabadi, M. Kamali-Gharamaleki, A. Saidipoor, H. Anaraki-Ardakani, J. Chem. Res., 644 (2007); doi:10.3184/030823407X266207.

H.R. Shaterian and H. Yarahmadi, Synlett, 916 (2006); doi:10.1055/s-2006-939034.

H.R. Shaterian and H. Yarahmadi, ARKIVOC, 105 (2007); doi:10.3998/ark.5550190.0009.212.

H.R. Shaterian, H. Yarahmadi and M. Ghashang, Bioorg. Med. Chem. Lett., 18, 788 (2008); doi:10.1016/j.bmcl.2007.11.035.

W.K. Su, W.Y. Tang, J.J. Li, J. Chem. Res., 123 (2008); doi:10.3184/030823408X298508.

B. Das, K. Laxminarayana, B. Ravikanth and R. Rao, J. Mol. Catal. Chem., 261, 180 (2007); doi:10.1016/j.molcata.2006.07.077.

L. Nagarapu, M. Baseeruddin, S. Apuri and S. Kantevari, Catal. Commun., 8, 1729 (2007); doi:10.1016/j.catcom.2007.02.008.

S.B. Patil, P.R. Singh, M.P. Surpur and S.D. Samant, Synth. Commun., 37, 1659 (2007); doi:10.1080/00397910701263858.

H.R. Shaterian, H. Yarahmadi and M. Ghashang, Tetrahedron, 64, 1263 (2008); doi:10.1016/j.tet.2007.11.070.

B. Das, D.N. Kumar, K. Laxminarayana and B. Ravikanth, Helv. Chim. Acta, 90, 1330 (2007); doi:10.1002/hlca.200790134.

H.R. Shaterian and H. Yarahmadi, Tetrahedron Lett., 49, 1297 (2008); doi:10.1016/j.tetlet.2007.12.093.

S. Kantevari, S.V.N. Vuppalapati and L. Nagarapu, Catal. Commun., 8, 1857 (2007); doi:10.1016/j.catcom.2007.02.022.

G. Srihari, M. Nagaraju and M.M. Murthy, Helv. Chim. Acta, 90, 1497 (2007); doi:10.1002/hlca.200790156.

(a) S.B. Patil, P.R. Singh, M.P. Surpur and S.D. Samant, Ultrason. Sonochem., 14, 515 (2007); doi:10.1016/j.ultsonch.2006.09.006; (b) R.R. Nagawade and D.B. Shinde, Chin. J. Chem., 25, 1710 (2007); doi:10.1002/cjoc.200790316.

R. Ghorbani-Vaghei and S.M. Malaekehpour, Cent. Eur. J. Chem., 8, 1086 (2010); doi:10.2478/s11532-010-0077-0.

(a) A. Kumar, M.S. Rao, I. Ahmad and B. Khungar, Can. J. Chem., 87, 714 (2009); doi:10.1139/V09-049; (b) H. Khabazzadeh, K. Saidi and N. Seyedi, J. Chem. Sci., 121, 429 (2009); doi:10.1007/s12039-009-0050-7; (c) A.R. Hajipour, F. Ghayeb, N. Sheikhan and A.E. Ruoho, Tetrahedron Lett., 50, 5649 (2009); doi:10.1016/j.tetlet.2009.07.116. (d) S.B. Sapkal, K.F. Shelke, B.R. Madje, B.B. Shingate and M.S. Shingare, Bull. Korean Chem. Soc., 30, 2887 (2009); doi:10.5012/bkcs.2009.30.12.2887; (e) T.T. She, Z.L. Liu and K. Gong, Chinese J. Appl. Chem., 27, 778 (2010).

(a) P.T. Anastas and J.C. Warner, Green Chemistry: Theory and Practice; Oxford University Press, Oxford, UK (1998); (b) P.T. Anastas and T. Williamson, Green Chemistry, Frontiers in Benign Chemical Synthesis and Process; Oxford University Press, Oxford, UK (1998).

(a) R. Duvedi and R.K. Singh, Asian J. Chem, 24, 5665 (2012); (b) S. Sharma, D.N. Prasad and R.K. Singh, J. Chem. Pharm. Res, 3, 382 (2011); (c) A. Sandhar, D.N. Prasad and R.K. Singh, Indian J. Heterocycl. Chem., 21, 369 (2012) (c) A. Sandhar, D.N. Prasad, A. Kapoor and R.K. Singh, Curr. Res. Chem, 4, 68 (2012); (d) S. Malik, S. Sharma and R.K. Singh, Asian J. Chem., 24, 5669 (2012); (e) P. Kaur, H. Sharma, R. Rana, D.N. Prasad and R.K. Singh, Asian J. Chem, 24, 5649 (2012); (f) A. Sandhar and R.K. Singh, Asian J. Chem, 24, 5643 (2012); (g) A. Sandhar and R.K. Singh, Chem. Sci. Trans., 2(S1), 176 (2012); doi:10.7598/cst2013.315.; (h) R.K. Singh, B. Singh, R. Duvedi and S. Kumar, Res. Chem. Intermed., (2014); doi:10.1007/s11164-013-1513-5.

R. Varala, R. Enugala and S.R. Adapa, J. Braz. Chem. Soc., 18, 291 (2007); doi:10.1590/S0103-50532007000200008.

Issue

Vol. 26 No. 16 (2014): Vol 26 Issue 16

Multicomponent One-pot Green Synthesis of 1-Amidoalkyl-2-naphthols Promoted by p-Nitrobenzoic Acid Under Solvent-free Condition

Corresponding Author(s) : Rajesh K. Singh

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