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

Volume: 28 Number: 3 May 2, 2015
EN

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

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

References

  1. Zhu, J. and Bienayme, H. “Multicomponent Reactions”, 1st, Wiley-VCH, Weinheim, (2005).
  2. 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).
  3. Kuthan, J. “Pyrans, thiopyrans, and selenopyrans”, Adv. Heterocycl. Chem. 34, pp. 145-303 (1983).
  4. 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).
  5. 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).
  6. 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).
  7. 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).
  8. 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).

Details

Primary Language

English

Subjects

-

Journal Section

-

Publication Date

May 2, 2015

Submission Date

May 2, 2015

Acceptance Date

-

Published in Issue

Year 2015 Volume: 28 Number: 3

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. https://izlik.org/JA37XR47DK
AMA
1.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):387-393. https://izlik.org/JA37XR47DK
Chicago
Behbahani, Farahnaz. 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): 387-93. https://izlik.org/JA37XR47DK.
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
[1]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, Oct. 2015, [Online]. Available: https://izlik.org/JA37XR47DK
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 1, 2015): 387-393. https://izlik.org/JA37XR47DK.
JAMA
1.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, Oct. 2015, pp. 387-93, https://izlik.org/JA37XR47DK.
Vancouver
1.Farahnaz Behbahani. ONE-POT SYNTHESIS OF 2-AMINO-4H-PYRANS AND 2-AMINO-TETRAHYDRO-4H-CHROMENES USING L-PROLINE. Gazi University Journal of Science [Internet]. 2015 Oct. 1;28(3):387-93. Available from: https://izlik.org/JA37XR47DK