Effectual direct synthesis of diversely substituted 4-aryl/alkyl coumarins by palladium catalyzed oxidative Suzuki–Miyaura coupling
Keywords:
4-aryl/alkylcoumarins, Suzuki-Miyaura coupling, Palladium catalyst, Boronic acid orAbstract
An effectual direct synthesis of 4-aryl/alkyl substituted coumarin was developed using a palladium-catalyzed oxidative Suzuki–Miyaura coupling reaction strategy. Use of Pd2(dba)3 in the presence of Na2CO3 in THF solvent was found to be the most effective reaction condition for excellent yield.
References
- Spath, E. Die natürlichen Cumarine. Berichte der Dtsch. Chem. Gesellschaft (A B Ser. 70, A83-A117 (1937).
- Jung, J.-C., Jung, Y.-J. & Park, O.-S. A CONVENIENT ONE-POT SYNTHESIS OF 4-HYDROXYCOUMARIN, 4-HYDROXYTHIOCOUMARIN, AND 4-HYDROXYQUINOLIN-2(1H)-ONE. Synth. Commun. 31, 1195-1200 (2001).
- Kostova, I., Raleva, S., Genova, P. & Argirova, R. Structure-Activity Relationships of Synthetic Coumarins as HIV-1 Inhibitors. Bioinorg. Chem. Appl. 2006, 68274 (2006).
- Harvey, R. G., Cortez, C., Ananthanarayan, T. P. & Schmolka, S. A new coumarin synthesis and its utilization for the synthesis of polycyclic coumarin compounds with anticarcinogenic properties. J. Org. Chem. 53, 3936-3943 (1988).
- Al-Haiza, M. a., Mostafa, M. S. & El-Kady, M. Y. Synthesis and Biological Evaluation of Some New Coumarin Derivatives. Molecules 8, 275-286 (2003).
- Musicki, B. et al. Improved antibacterial activities of coumarin antibiotics bearing 5?,5?-dialkylnoviose: biological activity of RU79115. Bioorg. Med. Chem. Lett. 10, 1695-1699 (2000).
- Moffett, R. B. Central Nervous System Depressants. VII.1 Pyridyl Coumarins. J. Med. Chem. 7, 446-449 (1964).
- Ruwet, A., Draguet, C. & Renson, M. Hydroxy-4 Thio-1 et Séléno-1 Coumarines voie Nouvelle de Synthèse. Bull. des Sociétés Chim. Belges 79, 639-644 (1970).
- Konstantina, C. F., Dimitra, J HadjipavlouLitina Konstantinos, E. L. & Demetrios, N. N. Natural and Synthetic Coumarin Derivatives with Anti-Inflammatory / Antioxidant Activities. Curr. Pharm. Des. 10, 3813-3833 (2004).
- Pillai, S. P., Menon, S. R., Mitscher, L. A., Pillai, C. A. & Shankel, D. M. Umbelliferone Analogues and Their Potential to Inhibit Benzo(a)pyrene- and Hydrogen Peroxide-Induced Mutations. J. Nat. Prod. 62, 1358-1362 (1999).
- Paya, M., Halliwell, B. & Hoult, J. R. S. Interactions of a series of coumarins with reactive oxygen species: Scavenging of superoxide, hypochlorous acid and hydroxyl radicals. Biochem. Pharmacol. 44, 205-214 (1992).
- Darbarwar, M. & V., S. Synthesis of Coumarins with 3:4-Fused Ring Systems and their Physiological Activity. Synthesis (Stuttg). 5, 377-388 (1982).
- Perkin, W. H. VI.-On the artificial production of coumarin and formation of its homologues. J. Chem. Soc. 21, 53-63 (1868).
- V. Pechmann, H. Neue Bildungsweise der Cumarine. Synthese des Daphnetins. I. Berichte der Dtsch. Chem. Gesellschaft 17, 929-936 (1884).
- Suvorov, N. N. & Dudinskaya, A. A. Hormones of thyroid gland and their analogs. II. Synthesis of isomers of betasine. Zhurnal Obs. Khimii 28, 1371-1374 (1958).
- Royer, R., Bodo, B., Demerseman, P. & Clavel, J. M. Reactions induced by pyridine hydrochloride. VII. Rearrangement of 2-methoxycinnamic acids to coumarins. Bull. Soc. Chim. Fr. 2929-2933 (1971).
- Avetisyan, A. A., Vanyan, E. V & Dangyan, M. T. Synthesis of functionally substituted coumarins. Chem. Heterocycl. Compd. 15, 959-960 (1979).
- Koepp, E. & Vogtle, F. Perkin-Synthese mit Cäsiumacetat. Synthesis (Stuttg). 2, 177-179 (1987).
- Shah, V., Bose, J. & Shah, R. Communication- New Synthesis of 4-Hydroxycoumarins. J. Org. Chem. 25, 677-678 (1960).
- Ziegler, E. & Junek, H. Zur Chemie des 4-Oxy-cumarins. Monatshefte für Chemie und verwandte Teile anderer Wissenschaften 86, 29-38 (1955).
- Ogawa, A., Kondo, K., Murai, S. & Sonoda, N. Selenium-assisted carbonylation of o-hydroxyacetophenone with carbon monoxide. J. Chem. Soc. Chem. Commun. 1283-1284 (1982). doi:10.1039/C39820001283
- Takumi, M. et al. Facile Synthesis of 4-Hydroxycoumarins by Sulfur-Assisted Carbonylation of 2?-Hydroxyacetophenones with Carbon Monoxide. Synthesis (Stuttg). 257-259 (1988).
- Lei, L., Yang, D., Liu, Z. & Wu, L. Mono-nitration of coumarins by nitric oxide. Synth. Commun. 34, 985-992 (2004).
- Majumdar, K. C. & Bhattacharyya, T. Studies of bioactive heterocycles: amino Claisen rearrangement of 4-N-(4-aryloxybut-2-ynyl),N-methylaminocoumarins. Tetrahedron Lett. 42, 4231-4233 (2001).
- Patel, D., Kumari, P. & Patel, N. Journal of Chemical and Pharmaceutical Research. 2, 84-91 (2010).
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Jaydip Rajpara, Arpit Radadia, Yogesh Naliapara "Effectual direct synthesis of diversely substituted 4-aryl/alkyl coumarins by palladium catalyzed oxidative Suzuki–Miyaura coupling" International Journal of Scientific Research in Science, Engineering and Technology (IJSRSET), Print ISSN : 2395-1990, Online ISSN : 2394-4099,
Volume 3, Issue 6, pp.230-237, September-October-2017.