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ONE-POT SYNTHESIS OF 2-AMINO-4H-PYRANS AND 2-AMINO-TETRAHYDRO-4H-CHROMENES USING L-PROLINE

Year 2015, Volume: 28 Issue: 3, 387 - 393, 02.05.2015

Abstract

A one-pot procedure for the synthesis of 2-amino-4-aryl-4H-pyrans and 2-amino-tetrahydro-4H-chromenes via the multi-component reaction between aryl aldehydes, β-dicarbonyl compounds and malononitrile in the presence of L-proline-in ethanol under reflux conditions has been developed rapidly and smoothly in good to excellent yields.

References

  • Zhu, J. and Bienayme, H. “Multicomponent Reactions”, 1st, Wiley-VCH, Weinheim, (2005).
  • Hafez, E.A., Elnagdi, M.H., Elagamey, A.A. and El-Taweel, F.A. “Nitriles in Heterocyclic Synthesis: Novel Synthesis of Benzo[c]coumarin and of Benzo[c]pyrano[3,2-c]quinoline Derivatives”, Heterocycles, 26, pp. 903-907 (1987).
  • Kuthan, J. “Pyrans, thiopyrans, and selenopyrans”, Adv. Heterocycl. Chem. 34, pp. 145-303 (1983).
  • Kumar, D., Reddy, V.B., Sharad, S., Dube, U. and Kapur, S. “A facile one-pot green synthesis and antibacterial activity of 2-amino-4H-pyrans and 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes”, Eur. J. Med. Chem. 44, pp. 3805-3809 (2009).
  • Suarez, M., Salfran, E., Verdecia, Y., Ochoa, E., Alba, L., Martin, N., Martinez, R., Quinteiro, M., Seoane, C., Novoa, H., Blaton, N., Peeters, O.M. and De Ranter, C. “X-Ray and theoretical structural study of novel 5,6,7,8-tetrahydrobenzo-4H-pyrans”, Tetrahedron 58, pp. 953-960 (2002).
  • Hekmatshoar, R., Majedi, S. and Bakhtiari, K. “Sodium selenate catalyzed simple and efficient synthesis of tetrahydro benzo[b]pyran derivatives”, Catal. Commun. 9, pp. 307-310 (2008).
  • Balalaie, S., Sheikh-Ahmadi, M. and Bararjaniam, M. “Tetra-methyl ammonium hydroxide: An efficient and versatile catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives in aqueous media”, Catal. Commun. 8, pp. 1724-1728 (2007).
  • Sabitha, G., Arundhathi, K., Sudhakar, K., Sastry, B.S. and Yaday, J.S. “Cerium(III) chloride-catalyzed one-pot synthesis of tetrahydrobenzo[b]pyrans” Synth. Commun. 39, pp. 433-442 (2009).
  • Kaupp, G., Naimi-Za Mal, M.R. and Schmeyers, J. “Solvent-free Knoevenagel condensations and Michael additions in the solid state and in the melt with quantitative yield”, Tetrahedron 59, pp. 3753-3760 (2003).
  • Behbahani, F.K. and Alaei, H.S. “L-Proline-catalysed synthesis of functionalized unsymmetrical dihydro-1H-indeno[1,2-b]pyridines”, J. Chem. Sci. 125, pp. 623-626 (2013).
  • Behbahani, F.K., Ghorbani, M., Sadeghpour, M. and Mirzaei, M. “L-Proline as reusable and organo catalyst for the one-pot synthesis of substituted 2-amino-4H-chromenes” Lett. Org. Chem. 10, pp. 191 (2013).
  • Liu, X.H., Fan, J.C., Liu, Y.Z. and Shang, C. “L-Proline as an efficient and reusable promoter for the synthesis of coumarins in ionic liquid”, J. Zhejiang. Univ. Sci. B 9, pp. 990-995 (2008).
  • Wang, H., Yang, C. and Han, K. “Density functional study of the l-proline-catalyzed α-aminoxylation of aldehydes reaction: The reaction mechanism and selectivity”, Struct. Chem. 17, pp. 97 (2006).
  • Al-Momani, L.A. “Hydroxy-L-prolines as asymmetric catalysts for aldol, Michael addition and Mannich reactions”, ARKIVOC VI, pp. 101-111 (2012).
  • Oskooie, H.A., Heravi, M.M., Karimi, N. and Ebrahim Zadeh, M. “Caro's acid-silica gel: an efficient and versatile catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives”, Synthetic Commun. 41, pp. 436-440 (2011).
  • Quintela, J.M., Peinador, C. and Moreira, M.J. “A novel synthesis of pyrano[2,3-d]pyrimidine derivatives” Tetrahedron 51, pp. 5901-5912 (1995).
  • Wang X.-S., Zeng. Z.-S., Zhang, M.-M. Li, Y.-L., Shi, D.-Q., Tu, S.-J., Wei, X.-Y. and Zong, Z.-M. “A convenient and clean procedure for the synthesis of pyran derivatives in aqueous media catalysed by TEBAC” J. Chem. Res. pp. 228-230 (2006).
Year 2015, Volume: 28 Issue: 3, 387 - 393, 02.05.2015

Abstract

References

  • Zhu, J. and Bienayme, H. “Multicomponent Reactions”, 1st, Wiley-VCH, Weinheim, (2005).
  • Hafez, E.A., Elnagdi, M.H., Elagamey, A.A. and El-Taweel, F.A. “Nitriles in Heterocyclic Synthesis: Novel Synthesis of Benzo[c]coumarin and of Benzo[c]pyrano[3,2-c]quinoline Derivatives”, Heterocycles, 26, pp. 903-907 (1987).
  • Kuthan, J. “Pyrans, thiopyrans, and selenopyrans”, Adv. Heterocycl. Chem. 34, pp. 145-303 (1983).
  • Kumar, D., Reddy, V.B., Sharad, S., Dube, U. and Kapur, S. “A facile one-pot green synthesis and antibacterial activity of 2-amino-4H-pyrans and 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes”, Eur. J. Med. Chem. 44, pp. 3805-3809 (2009).
  • Suarez, M., Salfran, E., Verdecia, Y., Ochoa, E., Alba, L., Martin, N., Martinez, R., Quinteiro, M., Seoane, C., Novoa, H., Blaton, N., Peeters, O.M. and De Ranter, C. “X-Ray and theoretical structural study of novel 5,6,7,8-tetrahydrobenzo-4H-pyrans”, Tetrahedron 58, pp. 953-960 (2002).
  • Hekmatshoar, R., Majedi, S. and Bakhtiari, K. “Sodium selenate catalyzed simple and efficient synthesis of tetrahydro benzo[b]pyran derivatives”, Catal. Commun. 9, pp. 307-310 (2008).
  • Balalaie, S., Sheikh-Ahmadi, M. and Bararjaniam, M. “Tetra-methyl ammonium hydroxide: An efficient and versatile catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives in aqueous media”, Catal. Commun. 8, pp. 1724-1728 (2007).
  • Sabitha, G., Arundhathi, K., Sudhakar, K., Sastry, B.S. and Yaday, J.S. “Cerium(III) chloride-catalyzed one-pot synthesis of tetrahydrobenzo[b]pyrans” Synth. Commun. 39, pp. 433-442 (2009).
  • Kaupp, G., Naimi-Za Mal, M.R. and Schmeyers, J. “Solvent-free Knoevenagel condensations and Michael additions in the solid state and in the melt with quantitative yield”, Tetrahedron 59, pp. 3753-3760 (2003).
  • Behbahani, F.K. and Alaei, H.S. “L-Proline-catalysed synthesis of functionalized unsymmetrical dihydro-1H-indeno[1,2-b]pyridines”, J. Chem. Sci. 125, pp. 623-626 (2013).
  • Behbahani, F.K., Ghorbani, M., Sadeghpour, M. and Mirzaei, M. “L-Proline as reusable and organo catalyst for the one-pot synthesis of substituted 2-amino-4H-chromenes” Lett. Org. Chem. 10, pp. 191 (2013).
  • Liu, X.H., Fan, J.C., Liu, Y.Z. and Shang, C. “L-Proline as an efficient and reusable promoter for the synthesis of coumarins in ionic liquid”, J. Zhejiang. Univ. Sci. B 9, pp. 990-995 (2008).
  • Wang, H., Yang, C. and Han, K. “Density functional study of the l-proline-catalyzed α-aminoxylation of aldehydes reaction: The reaction mechanism and selectivity”, Struct. Chem. 17, pp. 97 (2006).
  • Al-Momani, L.A. “Hydroxy-L-prolines as asymmetric catalysts for aldol, Michael addition and Mannich reactions”, ARKIVOC VI, pp. 101-111 (2012).
  • Oskooie, H.A., Heravi, M.M., Karimi, N. and Ebrahim Zadeh, M. “Caro's acid-silica gel: an efficient and versatile catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives”, Synthetic Commun. 41, pp. 436-440 (2011).
  • Quintela, J.M., Peinador, C. and Moreira, M.J. “A novel synthesis of pyrano[2,3-d]pyrimidine derivatives” Tetrahedron 51, pp. 5901-5912 (1995).
  • Wang X.-S., Zeng. Z.-S., Zhang, M.-M. Li, Y.-L., Shi, D.-Q., Tu, S.-J., Wei, X.-Y. and Zong, Z.-M. “A convenient and clean procedure for the synthesis of pyran derivatives in aqueous media catalysed by TEBAC” J. Chem. Res. pp. 228-230 (2006).
There are 17 citations in total.

Details

Primary Language English
Journal Section Chemistry
Authors

Farahnaz Behbahani

Publication Date May 2, 2015
Published in Issue Year 2015 Volume: 28 Issue: 3

Cite

APA Behbahani, F. (2015). ONE-POT SYNTHESIS OF 2-AMINO-4H-PYRANS AND 2-AMINO-TETRAHYDRO-4H-CHROMENES USING L-PROLINE. Gazi University Journal of Science, 28(3), 387-393.
AMA Behbahani F. ONE-POT SYNTHESIS OF 2-AMINO-4H-PYRANS AND 2-AMINO-TETRAHYDRO-4H-CHROMENES USING L-PROLINE. Gazi University Journal of Science. October 2015;28(3):387-393.
Chicago Behbahani, Farahnaz. “ONE-POT SYNTHESIS OF 2-AMINO-4H-PYRANS AND 2-AMINO-TETRAHYDRO-4H-CHROMENES USING L-PROLINE”. Gazi University Journal of Science 28, no. 3 (October 2015): 387-93.
EndNote Behbahani F (October 1, 2015) ONE-POT SYNTHESIS OF 2-AMINO-4H-PYRANS AND 2-AMINO-TETRAHYDRO-4H-CHROMENES USING L-PROLINE. Gazi University Journal of Science 28 3 387–393.
IEEE F. Behbahani, “ONE-POT SYNTHESIS OF 2-AMINO-4H-PYRANS AND 2-AMINO-TETRAHYDRO-4H-CHROMENES USING L-PROLINE”, Gazi University Journal of Science, vol. 28, no. 3, pp. 387–393, 2015.
ISNAD Behbahani, Farahnaz. “ONE-POT SYNTHESIS OF 2-AMINO-4H-PYRANS AND 2-AMINO-TETRAHYDRO-4H-CHROMENES USING L-PROLINE”. Gazi University Journal of Science 28/3 (October 2015), 387-393.
JAMA Behbahani F. ONE-POT SYNTHESIS OF 2-AMINO-4H-PYRANS AND 2-AMINO-TETRAHYDRO-4H-CHROMENES USING L-PROLINE. Gazi University Journal of Science. 2015;28:387–393.
MLA Behbahani, Farahnaz. “ONE-POT SYNTHESIS OF 2-AMINO-4H-PYRANS AND 2-AMINO-TETRAHYDRO-4H-CHROMENES USING L-PROLINE”. Gazi University Journal of Science, vol. 28, no. 3, 2015, pp. 387-93.
Vancouver Behbahani F. ONE-POT SYNTHESIS OF 2-AMINO-4H-PYRANS AND 2-AMINO-TETRAHYDRO-4H-CHROMENES USING L-PROLINE. Gazi University Journal of Science. 2015;28(3):387-93.