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

Farahnaz Behbahani

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.

Keywords

multicomponent; L-proline; 2-amino-4H-pyrans; chromenes; synthesis

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).