One-Pot Synthesis of Tetrahydrochromenochromene Diones Catalyzed by 3-carboxy-1-sulfopyridinium Chloride

Document Type : Research Article

Authors

Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, I.R. IRAN

Abstract

The development of new methods for the efficient preparation of heterocyclic compounds is an important issue in the synthesis of organic compounds in chemistry. Chromene derivatives play a considerable role in the synthesis of pharmaceutical compounds as a significant structural component in active and natural biological compounds. In this research, 3-carboxy-1-sulfopyridinium chloride ([NA-SO3H]+Cl-) was evaluated as a recoverable catalyst for the one-pot synthesis of dihydrochromenochromene derivatives by reaction of aryl aldehydes, 1,3-cyclohexanediones, and hydroxycoumarines in good to excellent yields in ethanol at 70 °C. The [NA-SO3H]+Cl- could be recycled several times without significant loss of its catalytic activity. Clean methodologies, easy work-up procedures, high yield, and simple preparation of the catalyst are some advantages of this procedure. All products were characterized by spectral data and by comparison with authentic samples reported in the literature.

Keywords

Main Subjects

References

[1]  Rotstein B. H., Zaretsky S., Rai V., Yudin A. K., Small heterocycles in multicomponent reactions, Chem. Rev., 114: 8323-8359 (2014).
[2]  Dömling A., Wang W., Wang K., Chemistry and biology of multicomponent reactions, Chem. Rev., 112: 3083-3135 (2012).
[3]  Dömling A., Recent developments in isocyanide based multicomponent reactions in applied chemistry, Chem. Rev., 106:17-89 (2006).
[4]  Elinson M. N., Dorofeev A. S., Feducovich S. K., Gorbunov S. V., Nasybullin R. F., Stepanov N. O., Nikishin G. I., Electrochemically induced chain transformation of salicylaldehydes and alkyl cyanoacetates into substituted 4H-chromenes, Tetrahedron Lett.,  47: 7629-7633 (2006).
[5]  Sun W., Cama L. J., Birzin E. T., Warrier S., Locco L., Mosley R., Hammond M. L., Rohrer S. P., 6H-Benzo[c]chromen-6-one derivatives as selective ERbeta agonists, Bioorg. Med. Chem. Lett., 16: 1468-1472 (2006).
[6]  Stachulski A. V., Berry N. G., Low A. C. L., Moores S. L., Row E., Warhurst D. C., Adagu I. S., Rossignol, J. F., Identification of isoflavone derivatives as effective anticryptosporidial agents in vitro and in vivo, J. Med. Chem., 49: 1450-1454 (2006).
[7]  Chen  Z., Zhu Q., Su W., Novel sulfonic acid functionalized ionic liquid catalyzed multicomponent synthesis of 10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-dione derivatives in water, Tetrahedron Lett., 52: 2601-2604 (2011).
[8]  Sun, X .J., Zhou, J. F., Zhi, S. J., Efficient one-pot synthesis of tetrahydrobenzo [c]xanthene-1,11-dione derivatives under microwave irradiation , Synth. Commun., 42: 1987-1995 (2012).
[9]  Anaraki-Ardakani H., Ghanavatian R., Akbari M., An efficient one-pot Synthesis of tetrahydro-chromeno [4,3-b]chromene-6,8-dione and tetrahydro-pyrano[4,3-b]chromene-1,9-dione derivatives under solvent-free conditions, World Appl. Sci. J., 22: 802-808 (2013).
[10]   Pradhan K., Paul S., Das A. R., An efficient Lewis acid-surfactant-combined catalyst (LASC) for the one pot synthesis of chromeno[4,3-b]chromene derivatives by assembling the basic building blocks, Tetrahedron Lett., 54: 3105-3110 (2013).
[11]   Maleki B., Green synthesis of bis-coumarin and dihydropyrano[3,2-c]chromene derivatives catalyzed by o-Benzenedisulfonimide, Org. Prep. Proced. Int. 48:303–318 (2016).
[12]   Jean K., Philippe H., "Nutrition for Healthy Skin: Strategies for Clinical and Cosmetic Practice", Springer Science & Business Media, 153 (2010).

Files

Share

How to cite

Statistics