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3-Coumaranone is used in the aurones, [2-benzylidenebenzofuran-3(2H)-ones] by reacting with appropriate aldehyde. It is involved in the condensation reaction with aldehydes in the presence of morpholine acetate to prepare substituted 2-(arylidene)benzofuran-3(ZH)-ones. In Horner-Wadsworth-Emmons reaction, it reacts with diethyl¬ cyanomethyl¬phosphonate to give 3-(cyanomethyl)benzofurans, which is an intermediate in the synthesis of antihyperglycemic agents.
3-Coumaranone and its substituted analogues undergo Horner-Wadsworth-Emmons reaction with Diethyl cyanomethylphosphonate, A10218, in the presence of NaH, to give 3-(cyanomethyl)benzofurans, intermediates in a synthesis of antihyperglycemic agents: J. Med. Chem., 35, 1176 (1992).
Condenses with aromatic aldehydes in the presence of alumina under mild conditions to give aurones, an important class of natural pigments: Tetrahedron Lett., 33, 5937 (1992):
Shu, C.; Liu, R.; Liu, S.; Li, J.; Yu, Y.; He, Q.; Lu, X.; Ye, L. Practical, Modular, and General Synthesis of 3-Coumaranones through Gold-Catalyzed Intermolecular Alkyne Oxidation Strategy. Chem. Asian J. 2015, 10 (1), 91-95.
Kuppusamy, R.; Gandeepan, P.; Cheng, C. RhIII-Catalyzed [4 + 1] Annulations of 2-Hydroxy- and 2-Aminobenzaldehydes with Allenes: A Simple Method toward 3-Coumaranones and 3-Indolinones. Org. Lett. 2015, 17 (15), 3846-3849.