A novel series of spiro[chromene-2,1'-cyclohexan]-4(3H)-one derivatives containing either a chalcone or flavanone fragment in their molecules was synthesized. 2'-Hydroxychalcones, containing a spirochromanone moiety, underwent cyclocondensation with formation of a condensed pyran ring. The catalytic efficiency of TFA in the chalcone–flavanone transformation has been demonstrated. The structures of the compounds have been established on the basis of elemental analysis and standard spectroscopic data. The synthesized compounds were tested for their antibacterial and antifungal activities.
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(a) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893. (b) Schweizer, E. E.; Meeder-Nycz, D. In Chemistry of Heterocyclic Compounds: Chromenes, Chromanones, and Chromones; Ellis, G. P., Ed.; Wiley: New York, 1977, vol. 31, p. 11. (c) Harborne, J. B.; Williams, C. A. Phytochemistry 2000, 55, 481. (d) Hepworth, J. D. In Comprehensive Heterocyclic Chemistry; Katrizky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984, vol. 3, p. 737.
(a) Muthukrishnan, M.; Patil, P. S.; More, S. V.; Joshi, R. A. Mendeleev Commun. 2005, 100. (b) Muthukrishnan, M.; Basavanag, U. M. V.; Puranik, V. G. Tetrahedron Lett. 2009, 50, 2643. (c) Singh, O. V.; Muthukrishnan, M.; Sundaravadivelu, M. Indian J. Chem. 2005, 44B, 2575. (d) Singh, O. V.; Muthukrishnan, M.; Gopan, R. Synth. Commun. 2005, 35, 2723. (e) Muthukrishnan, M.; Singh, O. V. Synth. Commun. 2008, 38, 3875.
Dhar, D. N. The Chemistry of Chalcones and Related Compounds; John Wiley & Sons: New York, 1981.
Kumar, D.; Kumar, N. M.; Akamatsu, K.; Kusaka, E.; Harada, H.; Ito, T. Bioorg. Med. Chem. Lett. 2010, 20, 3916.
Vogel, S.; Barbic, M.; Jurgenliemk, G.; Heilmann, J. Eur. J. Med. Chem. 2010, 45, 2206.
(a) Dimmock, J. R.; Elias, D. W.; Beazely, M. A.; Kandepu, N. M. Curr. Med. Chem. 1999, 6, 1125. (b) Nowakowska, Z. Eur. J. Med. Chem. 2007, 42, 125. (c) Kontogiorgis, C.; Mantzanidou, M.; Hadjipavlou-Litina, D. Mini-Rev. Med. Chem. 2008, 8, 1224.
(a) Patonay, T.; Litkei, G.; Zsuga, M.; Kiss, A. Org. Prep. Proced. Int. 1984, 16, 315. (b) Harwood, L. M.; Loftus, G. C.; Oxford, A.; Thomson, C. Synth. Commun. 1990, 20, 649. (c) Wurm, G.; Nordmann, M. Arch. Pharm. 1988, 321, 555.
(a) Ashok, D.; Sudershan, K.; Khalilullah, M. Green Chem. Lett. Rev. 2012, 5, 121. (b) Ashok, D.; Shravani, D. Asian J. Chem. 2009, 21, 808. (c) Ashok, D.; Ravi, S.; Lakshmi, B. V.; Ganesh, A.; Adam, S. Russ. J. Gen. Chem. 2016, 42, 323. (d) Ashok, D.; Shravani, D.; Sarasija, M. Asian J. Chem. 2009, 21, 96727.
(a) Ashok, D.; Lakshmi, B. V.; Ravi, S.; Ganesh, A.; Adam, S. Chem. Heterocycl. Compd. 2015, 51, 462. [Khim. Geterotsikl. Soedin. 2015, 51, 462.] (b) Ashok, D.; Gandhi, D. M.; Kumar, A. V.; Gundu, S. Chem. Heterocycl. Compd. 2015, 51, 872. [Khim. Geterotsikl. Soedin. 2015, 51, 872.] (c) Ashok, D.; Kifah, M. A.; Lakshmi, B. V.; Sarasija, M.; Adam, S. Chem. Heterocycl. Compd. 2016, 52, 172. [Khim. Geterotsikl. Soedin. 2016, 52, 172.] (d) Ashok, D.; Padmavati, K.; Lakshmi, B. V.; Sarasija, M. Chem. Heterocycl. Compd. 2016, 52, 15. [Khim. Geterotsikl. Soedin. 2016, 52, 15.] (e) Ashok, D.; Kumar, R. S.; Gandhi, D. M.; Jayashree, A. Chem. Heterocycl. Compd. 2016, 52, 453. [Khim. Geterotsikl. Soedin. 2016, 52, 453.]
(a) Grassi, D.; Desideri, G.; Croce, G.; Tiberti, S.; Aggio, A.; Ferri, C. Curr. Pharm. Des. 2009, 10, 1072. (b) Harborne, J. B.; Williams, C. A. Phytochemistry 2000, 55, 481.
Bravo, L. Nutr. Rev. 1986, 56, 317.
Sharghi, H. J. Chem. Res., Synop. 1998, 10, 628.
Rostamizadeh, S.; Zekri, N.; Tahershamsi, L. Chem. Heterocycl. Compd. 2015, 51, 526. [Khim. Geterotsikl. Soedin. 2015, 51, 526.]
Ashok, D.; Shravani, D. Tetrahedron Lett. 2008, 49, 7227.
Mujahid, M.; Yogeeswari, P.; Sriram, D.; Basavanag, U. M. V.; Díaz-Cervantes, E.; Córdoba-Bahena, L., Robles, J.; Gonnade, R. G.; Karthikeyan, M.; Renu, V.; Muthukrishnan, M. RSC Adv. 2015, 5, 106448.
Emara, A. A. A.; Abou-Hussen, A. A. A. Spectrochim. Acta, Part A 2006, 64, 1010.
(a) Brennan, C. M.; Hunt, I.; Jarvis, T. C.; Johnson, C. D.; McDonnell, P. D. Can. J. Chem. 1990, 68, 1780. (b) Bradley, J. P.; Jarvis, T. C.; Johnson, C. D.; McDonnell, P. D.; Weatherstone, T. A. P. Tetrahedron Lett. 1983, 24, 2851. (c) Wu, Y.-C.; Liu, L.; Liu, Y.-L.; Wang, D.; Chen, Y.-J. J. Org. Chem. 2007, 72, 9383.
(a) Sagrera, G. J.; Seoane, G. A. J. Braz. Chem. Soc. 2005, 16, 851. (b) Shakil, N. A.; Singh, M. K.; Sathiyendiran, M.; Kumar, J. Arch. Phytopathol. Plant Prot. 2011, 44, 1958.
Safavi, M.; Esmati, N.; Ardestani, S. K.; Emami, S.; Ajdari, S.; Davoodi, J.; Shafiee, A.; Foroumadi, A. Eur. J. Med. Chem. 2012, 58, 573.
Kavala, V.; Lin, C.; Kuo, C.-W.; Fang, H.; Yao, C.-F. Tetrahedron 2012, 68, 1321.
Benson, H. J. Microbiological Applications: A Laboratory Manual in General Microbiology; 7th edn.; McGraw Hill: Boston, 1998, p. 139.
Saha, K.; Mukherjee Pulok, K.; Mandal, S. C.; Pal, M.; Saha, B. P. Indian Drugs 1995, 32, 402.
The authors are grateful to the Head, Department of Chemistry, Osmania University, Hyderabad, and JNTU-H Hyderabad for providing analytical facilities. The authors are grateful to Vishnu Chemicals limited, Jeedimetla, and Department of Chemistry, Anurag group of Institutions for providing laboratory facilities.
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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(5), 511–517
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Ramana Kishore, N., Ashok, D., Rao, B.A. et al. Simple and efficient route for the synthesis of functionalized 2,3,7,8-tetrahydro-4H,6H-pyrano[3,2-g]chromene-4,6-diones. Chem Heterocycl Comp 53, 511–517 (2017). https://doi.org/10.1007/s10593-017-2085-x
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DOI: https://doi.org/10.1007/s10593-017-2085-x