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An Economical and Green Synthesis of Spiro[diindeno [1,2- b:2,1-e]pyridine-11,3-indoline]-trione Derivatives through Multi-Component Reaction by Br¢nsted Acidic Ionic Liquid Catalyst

Year 2015, Volume: 28 Issue: 2, 195 - 199, 22.06.2015

Majid Heravi Zeinab Teymuri Narges Karimi , Yahya Beheshtiha Niloofar Tavakoli

Abstract

Synthesis of spiro[diindenopyridine-indoline]-triones by one-pot condensation of 1,3-indandione, isatin and aniline by Brønsted acid ionic liquid (BAIL),1-(4-sulfonicacid)butyl-3-methylimidazolium hydrogen sulfate ([(CH2)4SO3HMIM][HSO4]), as reusable and an economical catalyst in water under reflux condition.

Keywords

Water Ionic liquid Isatin Aniline 1,3-indandione

References

  • Li, C.J. and Chan, T.H. Organic reactions in aqueous media. Wiley, New York. Grieco, P.A. Thomson Science, Glasgow, Scotland. Li, C.J., “Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations”, A Decade Update; Chem. Rev. 105: 3095-3166.
  • Duan, X.H., Liu, X.Y., Guo, L.N., Liao, M.C., Liu, W.M. and Liang, Y.M., “Palladium- Catalyzed one- pot synthesis of highly substituted furans by a three- component annulation reaction”, J. Org. Chem. 70: 6980-6983 (2005).
  • Zhu, J. Bienayme(Eds.), H., “Multicomponent Reactions”, Wiley-VCH, Weinheim, 2005.
  • Wilcox, R.W, "The treatment of influenza in adults", Medical News, 15: 931-932 (1900).
  • Junck, H., and Sterk, H. “Synthesen mit nitrilen, mitt.: die partielle retro-michael-addition von tetracyanäthylen an indandion-1,3”, Tetrahedron Lett. 40: 4309-4310 91968).
  • Xue, J., Zhang, Y., Wang, X.I., Fun, H.K. and Xu, J.- H., “Photoinduced reactions of 1-Acetylisatin with Phenylacetylenes”, Org. Lett. 2: 2583-2586 (2000).
  • Marti, C.; Carreira, E.M., “Inspiration from Natural Products”, Eur. J. Org. Chem. 2209-2219 (2003).
  • Jain, N., Kumar, A.,Chauhan, S. and Chauhan, S.M.S., “Chemical and biochemical transformations in ionic liquids”, Tetrahedron 61: 1015-1060 (2005).
  • Gu, Y., Shi, F. and Deng, Y., Esterification of „ aliphatic acids with olefin promoted by Brİnsted acidic ionic liquids”, J. Mol. Catal. A: Chem. 212: 71- 75 (2004).
  • Gu, Y., Zhang, J., Duan Z. and Deng, Y., “Pechmann Reaction in Non-Chloroaluminate Acidic Ionic Liquids under Solvent-Free Conditions”, Adv. Synth. Catal. 347: 512-516 (2005).
  • Cole, A.C., Jensen, J.L., Ntai, L., Tran, K.L.T., Weaver, K.J., Forbes, D.C. and Davis, J.H. “Novel Brİnsted Acidic Ionic Liquids and Their Use as Dual Solvent−Catalysts”, J. Am. Chem. Soc. 124: 5962- 5963 (2002).
  • Heravi, M.M., Saeedi, M., Karimi, N., Zakeri, M., Beheshtiha, Y.S. and Davoodnia, A., “Brİnsted Acid Ionic Liquid [(CH2)4SO3HMIM][HSO4] as Novel Catalyst for One-Pot Synthesis of Hantzsch Polyhydroquinoline Derivatives”, Synth. Commun. 40: 523-529 (2010).
  • Wang, W., Shao, L., Cheng, W., Yang, J. and He, M., “Brİnsted acidic ionic liquids as novel catalysts for Prins reaction”, Catal. Commun. 9: 337-341 (2008).
  • Heravi, M.M., Zakeri,M., Karimi, N., Saeedi, M., Oskooie, H.A. and Tavakoli, N.H., “Acidic Ionic Liquid [(CH2)4SO3HMIM][HSO4] a green media for the simple and straightforward synthesis of 2,4,5- trisubstituted imidazoles”, Synth. Commun. 40: 1998- 2006 (2010).
  • Ghahremanzadeh, R., Shakibaei, G.I., Ahadi S. and Bazgir, A., “One-Pot, Pseudo Four-Component Synthesis of a Spiro[diindeno[1,2-b:2′,1′-e]pyridine- 11,3′-indoline]-trione Library”, J. Comb. Chem. 12: 191-194 (2010).

Year 2015, Volume: 28 Issue: 2, 195 - 199, 22.06.2015

Majid Heravi Zeinab Teymuri Narges Karimi , Yahya Beheshtiha Niloofar Tavakoli

Abstract

References

  • Li, C.J. and Chan, T.H. Organic reactions in aqueous media. Wiley, New York. Grieco, P.A. Thomson Science, Glasgow, Scotland. Li, C.J., “Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations”, A Decade Update; Chem. Rev. 105: 3095-3166.
  • Duan, X.H., Liu, X.Y., Guo, L.N., Liao, M.C., Liu, W.M. and Liang, Y.M., “Palladium- Catalyzed one- pot synthesis of highly substituted furans by a three- component annulation reaction”, J. Org. Chem. 70: 6980-6983 (2005).
  • Zhu, J. Bienayme(Eds.), H., “Multicomponent Reactions”, Wiley-VCH, Weinheim, 2005.
  • Wilcox, R.W, "The treatment of influenza in adults", Medical News, 15: 931-932 (1900).
  • Junck, H., and Sterk, H. “Synthesen mit nitrilen, mitt.: die partielle retro-michael-addition von tetracyanäthylen an indandion-1,3”, Tetrahedron Lett. 40: 4309-4310 91968).
  • Xue, J., Zhang, Y., Wang, X.I., Fun, H.K. and Xu, J.- H., “Photoinduced reactions of 1-Acetylisatin with Phenylacetylenes”, Org. Lett. 2: 2583-2586 (2000).
  • Marti, C.; Carreira, E.M., “Inspiration from Natural Products”, Eur. J. Org. Chem. 2209-2219 (2003).
  • Jain, N., Kumar, A.,Chauhan, S. and Chauhan, S.M.S., “Chemical and biochemical transformations in ionic liquids”, Tetrahedron 61: 1015-1060 (2005).
  • Gu, Y., Shi, F. and Deng, Y., Esterification of „ aliphatic acids with olefin promoted by Brİnsted acidic ionic liquids”, J. Mol. Catal. A: Chem. 212: 71- 75 (2004).
  • Gu, Y., Zhang, J., Duan Z. and Deng, Y., “Pechmann Reaction in Non-Chloroaluminate Acidic Ionic Liquids under Solvent-Free Conditions”, Adv. Synth. Catal. 347: 512-516 (2005).
  • Cole, A.C., Jensen, J.L., Ntai, L., Tran, K.L.T., Weaver, K.J., Forbes, D.C. and Davis, J.H. “Novel Brİnsted Acidic Ionic Liquids and Their Use as Dual Solvent−Catalysts”, J. Am. Chem. Soc. 124: 5962- 5963 (2002).
  • Heravi, M.M., Saeedi, M., Karimi, N., Zakeri, M., Beheshtiha, Y.S. and Davoodnia, A., “Brİnsted Acid Ionic Liquid [(CH2)4SO3HMIM][HSO4] as Novel Catalyst for One-Pot Synthesis of Hantzsch Polyhydroquinoline Derivatives”, Synth. Commun. 40: 523-529 (2010).
  • Wang, W., Shao, L., Cheng, W., Yang, J. and He, M., “Brİnsted acidic ionic liquids as novel catalysts for Prins reaction”, Catal. Commun. 9: 337-341 (2008).
  • Heravi, M.M., Zakeri,M., Karimi, N., Saeedi, M., Oskooie, H.A. and Tavakoli, N.H., “Acidic Ionic Liquid [(CH2)4SO3HMIM][HSO4] a green media for the simple and straightforward synthesis of 2,4,5- trisubstituted imidazoles”, Synth. Commun. 40: 1998- 2006 (2010).
  • Ghahremanzadeh, R., Shakibaei, G.I., Ahadi S. and Bazgir, A., “One-Pot, Pseudo Four-Component Synthesis of a Spiro[diindeno[1,2-b:2′,1′-e]pyridine- 11,3′-indoline]-trione Library”, J. Comb. Chem. 12: 191-194 (2010).
There are 15 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Chemistry
Authors

Majid Heravi This is me

Zeinab Teymuri This is me

Narges Karimi

Yahya Beheshtiha This is me

Niloofar Tavakoli This is me

Publication Date June 22, 2015
Published in Issue Year 2015 Volume: 28 Issue: 2

Cite

APA Heravi, M., Teymuri, Z., Karimi, N., Beheshtiha, Y., et al. (2015). An Economical and Green Synthesis of Spiro[diindeno [1,2- b:2,1-e]pyridine-11,3-indoline]-trione Derivatives through Multi-Component Reaction by Br¢nsted Acidic Ionic Liquid Catalyst. Gazi University Journal of Science, 28(2), 195-199.
AMA Heravi M, Teymuri Z, Karimi N, Beheshtiha Y, Tavakoli N. An Economical and Green Synthesis of Spiro[diindeno [1,2- b:2,1-e]pyridine-11,3-indoline]-trione Derivatives through Multi-Component Reaction by Br¢nsted Acidic Ionic Liquid Catalyst. Gazi University Journal of Science. June 2015;28(2):195-199.
Chicago Heravi, Majid, Zeinab Teymuri, Narges Karimi, Yahya Beheshtiha, and Niloofar Tavakoli. “An Economical and Green Synthesis of Spiro[diindeno [1,2- b:2,1-e]pyridine-11,3-Indoline]-Trione Derivatives through Multi-Component Reaction by Br¢nsted Acidic Ionic Liquid Catalyst”. Gazi University Journal of Science 28, no. 2 (June 2015): 195-99.
EndNote Heravi M, Teymuri Z, Karimi N, Beheshtiha Y, Tavakoli N (June 1, 2015) An Economical and Green Synthesis of Spiro[diindeno [1,2- b:2,1-e]pyridine-11,3-indoline]-trione Derivatives through Multi-Component Reaction by Br¢nsted Acidic Ionic Liquid Catalyst. Gazi University Journal of Science 28 2 195–199.
IEEE M. Heravi, Z. Teymuri, N. Karimi, Y. Beheshtiha, and N. Tavakoli, “An Economical and Green Synthesis of Spiro[diindeno [1,2- b:2,1-e]pyridine-11,3-indoline]-trione Derivatives through Multi-Component Reaction by Br¢nsted Acidic Ionic Liquid Catalyst”, Gazi University Journal of Science, vol. 28, no. 2, pp. 195–199, 2015.
ISNAD Heravi, Majid et al. “An Economical and Green Synthesis of Spiro[diindeno [1,2- b:2,1-e]pyridine-11,3-Indoline]-Trione Derivatives through Multi-Component Reaction by Br¢nsted Acidic Ionic Liquid Catalyst”. Gazi University Journal of Science 28/2 (June 2015), 195-199.
JAMA Heravi M, Teymuri Z, Karimi N, Beheshtiha Y, Tavakoli N. An Economical and Green Synthesis of Spiro[diindeno [1,2- b:2,1-e]pyridine-11,3-indoline]-trione Derivatives through Multi-Component Reaction by Br¢nsted Acidic Ionic Liquid Catalyst. Gazi University Journal of Science. 2015;28:195–199.
MLA Heravi, Majid et al. “An Economical and Green Synthesis of Spiro[diindeno [1,2- b:2,1-e]pyridine-11,3-Indoline]-Trione Derivatives through Multi-Component Reaction by Br¢nsted Acidic Ionic Liquid Catalyst”. Gazi University Journal of Science, vol. 28, no. 2, 2015, pp. 195-9.
Vancouver Heravi M, Teymuri Z, Karimi N, Beheshtiha Y, Tavakoli N. An Economical and Green Synthesis of Spiro[diindeno [1,2- b:2,1-e]pyridine-11,3-indoline]-trione Derivatives through Multi-Component Reaction by Br¢nsted Acidic Ionic Liquid Catalyst. Gazi University Journal of Science. 2015;28(2):195-9.