Abstract
Petroleum ether-benzene extract of the leaves of Ficus krishnae afforded a novel halogenated 2H-chromen-2-one named 3-chloro-7-methoxy-4-methyl-chromen-2-one. Its structure was established on basis of chemical and physical evidence (IR, 1H NMR, and MS data) as well as on X-ray crystallographic studies.
This is a preview of subscription content, log in via an institution to check access.
References
Abaul, J., Philogène, É., Bourgeois, P., Poupat, C., Ahond, A., & Potier, P. (1994). Contribution à la connaissance des rutacées américaines: Étude des feuilles de Triphasia trifolia. Journal of Natural Products, 57, 846–848. DOI: 10.1021/np50108a028.
Avramenko, L. G., & Nikonov, G. K. (1971). Saxalin-A new furocoumarin from the roots of Angelica saxatilis. Chemistry of Natural Compounds, 7, 804–805. DOI: 10.1007/BF00567948.
Batanero, B., Pérez, M. J., & Barba, F. (1999). Electrosynthesis of 3-chloro-4-substituted-coumarins. Journal of Electroanalytical Chemistry, 469, 201–205. DOI: 10.1016/S0022-0728(99)00198-9.
Beier, R. C., Ivie, G. W., & Oertli, E. H. (1994). Linear furanocoumarins and graveolone from the common herb parsley. Phytochemistry, 36, 869–872. DOI: 10.1016/S0031-9422(00)90453-9.
Billeret, D., Blondeau, D., & Sliwa, H. (1993). Convenient synthesis of 5-azacoumarins. Journal of Heterocyclic Chemistry, 30, 671–674. DOI: 10.1002/jhet.5570300316.
Bruker (2003). APEX2 and SAINT. Madison, WI, USA: Bruker AXS Inc.
Chen, Y. L., Wang, T. C., Chang, N. C., Chang, Y. L., Teng, C. M., & Tzeng, C. C. (1998). Alpha-mehtylene-gammabutyrolactones: synthesis and vasorelaxing activity assay of coumarin, naphthalene and quinoline derivatives. Chemical and Pharmaceutical Bulletin, 46, 962–965.
Chexal, K. K., Tamm, C., Hirotsu, K., & Clardy, J. (1979). Gilmaniellin and dechlorogilmaniellin, two novel dimeric oxaphenalenones. Helvetica Chimica Acta, 62, 1785–1803. DOI: 10.1002/hlca.19790620611.
de Melo, J. S. S., Becker, R. S., & Macanita, A. L. (1994). Photophysical behavior of coumarins as a function of substitution and solvent: experimental, evidence for the existence of a lowest lying 1(n,.pi.*) state. The Journal of Physical Chemistry, 98, 6054–6058. DOI: 10.1021/j100075a002.
González, A. G., Barroso, J. T., Diaz Chico, E., Luis, J. G., & Rodríguez, L. F. (1976). Compounds of the umbelliferae. XI. New coumarins from Heracleum pyrenaicum Lan. Anales de Química, 72, 584–585.
González, A. G., Barroso, J. T., Luis, J. R., & Rodríguez, L. F. (1974). Compounds of umbelliferae. III. Structure of a new coumarin of Heracleum granatense. Anales de Química, 70, 856–857.
Grover, J. K. (1952). Synthesis of 3-chloro-4-substituted coumarins with a variety of chlorinating agents. Journal of Scientific and Industrial Research, 11B, 50–55.
Ignaťeva, N. S., Vandyshev, V. V., & Pimenov, M. G. (1972). Coumarin from the roots of Cachrys pubescens. Chemistry of Natural Compounds, 3, 381. DOI: 10.1007/BF00563757.
Ilyas, M., Parveen, M., Shafiullah, & Sohrab, M. (1996). Phenolic constituents of Ficus krishnae. Journal of the Indian Chemical Society, 73, 632.
Ito, C., Furukawa, H., Ishii, H., Ishikawa, T., & Haginiwa, J. (1990). The chemical composition of Murraya paniculata. The structure of five new coumarins and one new alkaloid and the stereochemistry of murrangatin and related coumarins. Journal of the Chemical Society, Perkin Transactions 1, 1990, 2047–2055. DOI: 10.1039/P19900002047.
Ivie, G. W. (1978). Linear furocoumarins (psoralens) from the seed of Texas Ammi majus L. (Bishop’s Weed). Journal of Agricultural and Food Chemistry, 26, 1394–1403. DOI: 10.1021/jf60220a023.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M., & van de Streek, J. (2006). Mercury: visualization and analysis of crystal structures. Journal of Applied Crystallography, 39, 453–457. DOI: 10.1107/S002188980600731X.
Parveen, M., Sohrab, M., & Ilyas, M. (1993). Chemical constituents of Ficus krishnae. Journal of the Indian Chemical Society, 70, 785.
Silva, P. S. P., Parveen, M., Ali, A., & Ramos Silva. M. (2011). 8-Iodo-5,7-dimethoxy-4-methyl-2H-chromen-2-one. Acta Crystallographica Section E, 67, o776. DOI: 10.1107/S1600536811007549.
Silva, P. S. P., Parveen, M., Khanam, Z., Ali, A., & Ramos Silva, M. (2010). 6,8-Diiodo-5,7-dimethoxy-4-methylcoumarin. Acta Crystallographica Section E, 66, o988. DOI: 10.1107/S1600536810011360.
Sharma, P. N., Shoeb, A., Kapil, R. S., & Popli, S. P. (1981). Toddanol and toddanone, two coumarins from Toddalia asiatica. Phytochemistry, 20, 335–336. DOI: 10.1016/0031-9422(81)85120-5.
Sheldrick, G. M. (2003). SADABS, Version 2.10. Göttingen, Germany: University of Göttingen.
Sheldrick, G. M. (2008). A short history of SHELX. Acta Crystallographica Section A, 64, 112–122. DOI: 10.1107/S0108767307043930.
Sood, S., Gupta, B. D., Banerjee, S. K., & Rao, P. R. (1978). Coumarins from the umbels of Prangos pabularia. Journal of the Indian Chemical Society, 55, 850–851.
Thapliyal, P. C., Singh, P. K., & Khanna, R. N. (1994). Copper (II) halides adsorbed on alumina as halogenating reagent for coumarins. ChemInform, 25, 2821–2826. DOI: 10.1002/chin.199416171.
Trost, B. M., Toste, F. D., & Greenman, K. (2003). Atom economy. Palladium-catalyzed formation of coumarins by addition of phenols and alkynoates via a Net C-H insertion. Journal of the American Chemical Society, 125, 4518–4526. DOI: 10.1021/ja0286573.
Zheleva, A. B., Mahandru, M.M., & Bubeva-Ivanova, L. (1976). Four new coumarins from the roots of Peucedanum arenarium. Phytochemistry, 15, 209–210. DOI: 10.1016/S0031-9422(00)89086-X.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Parveen, M., Ali, A., Malla, A.M. et al. A halogenated coumarin from Ficus krishnae . Chem. Pap. 65, 735–738 (2011). https://doi.org/10.2478/s11696-011-0055-9
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.2478/s11696-011-0055-9