One Pot Multicomponent Synthesis of Pyranopyrazoles using Tetra Butyl Ammonium Bromide as Catalyst in Aqueous Media

  • Amol M. Pachpinde
  • Mallinath M. Langade
Keywords: Aromatic Aldehydes, Malononitrile, Ethylacetoacetate, Pyranopyrazoles, TBAB

Abstract

A four-component one-pot method to synthesize pyranopyrazoles from aromatic aldehydes, malononitrile, ethylacetoacetate and hydrazinehydrate using tetrabutyl ammonium bromide as a catalyst (20 mol %) in aqueous media is described herein. This method is simple and provides several advantages such as, good yields, short reaction time, environmentally friendly and mild reaction conditions. Use of environmentally benign water as a solvent is also a major advantage of using this method.

 

Downloads

Download data is not yet available.

References

Evdokimov, N. M., Kireev, A. S., Yakovenko, A. A., Antipin, M. Y., Magedov, I. V., Kornienko, A., (2007). J. Org. Chem. 72, 344

Li, C.J., Chan, T.H., (1997). Organic Reaction in Aqueous Media ,Wiley: New York.

Anastas, P. T., Warner, J. C., (1998). Green Chemistry: Theory and Practice Oxford University Press; Oxford, U P. T.K.

Samai, S., Nandi, G. C., Kumar, R., & Singh, M. S. (2009). Multicomponent one-pot solvent-free synthesis of functionalized unsymmetrical dihydro-1H-indeno [1, 2-b] pyridines. Tetrahedron Letters, 50(50), 7096-7098.

Herrerias, C. I., Yao, X., Li, Z., & Li, C. J. (2007). Reactions of C− H bonds in water. Chemical reviews, 107(6), 2546-2562.

Klijn, J. E., & Engberts, J. B. (2005). Fast reactions ‘on water’. Nature, 435(7043), 746-747.

Junek, H., & Aigner, H. (1973). Synthesen mit Nitrilen, XXXV. Reaktionen von tetracyanäthylen mit heterocyclen. Chemische Berichte, 106(3), 914-921.

Sharanin Yu, A., Sharanina, L. G., Puzanova, V. V., 1983. Zh. Org. Khim. 19, 2609.

Sharanin, Yu.A., Sharanina, L.G.,Puzanova, V.V.J.,1983. Org. Chem. USSR, 221

Foloppe, N., Fisher, L. M., Howes, R., Potter, A., Robertson, A. G., & Surgenor, A. E. (2006). Identification of chemically diverse Chk1 inhibitors by receptor-based virtual screening. Bioorganic & medicinal chemistry, 14(14), 4792-4802.

Mizar, P., & Myrboh, B. (2008). Three-component synthesis of 5: 6 and 6: 6 fused pyrimidines using KF–alumina as a catalyst. Tetrahedron Letters, 49(36), 5283-5285.

Kanagaraj, K., & Pitchumani, K. (2010). Solvent-free multicomponent synthesis of pyranopyrazoles: per-6-amino-β-cyclodextrin as a remarkable catalyst and host. Tetrahedron Letters, 51(25), 3312-3316.

Mecadon, H., Rohman, M. R., Rajbangshi, M., & Myrboh, B. (2011). γ-Alumina as a recyclable catalyst for the four-component synthesis of 6-amino-4-alkyl/aryl-3-methyl-2, 4-dihydropyrano [2, 3-c] pyrazole-5-carbonitriles in aqueous medium. Tetrahedron Letters, 52(19), 2523-2525.

Published
2018-09-29
How to Cite
Amol M. Pachpinde, & Mallinath M. Langade. (2018). One Pot Multicomponent Synthesis of Pyranopyrazoles using Tetra Butyl Ammonium Bromide as Catalyst in Aqueous Media. International Journal for Research in Applied Sciences and Biotechnology, 5(5), 29-31. https://doi.org/10.31033/ijrasb.5.5.5