Synthesis of functionalized hydroxyphthalides and their conversion to 3-cyano-1 (3H)-isobenzofuranones. The Diels-Alder reaction of methyl 4, 4-diethoxybutynoate …
…, GW Morrow, JS Swenton
Index: Freskos, John N.; Morrow, Gary W.; Swenton, John S. Journal of Organic Chemistry, 1985 , vol. 50, # 6 p. 805 - 810
Full Text: HTML
Citation Number: 87
Abstract
Several methods have been used in the preparation of functionalized hydroxyphthalides. Metalation of N, N-diethyl-3-methoxybenzamide, followed by reaction with dimethylformamide and hydrolysis, furnished 3-hydroxy-4-methoxy-l (3H)-isobenzofuranone in 52% yield. Reaction of the metalation product of m-fluorobenzaldehyde dimethyl acetal with carbon dioxide, followed by hydrolysis, gave 3-hydroxy-7-fluoro-l (3H)-iso- ...
Related Articles:
[Trost, Barry M.; Rivers, Gordon T.; Gold, Jeffrey M. Journal of Organic Chemistry, 1980 , vol. 45, # 10 p. 1835 - 1838]
[Mal, Dipakranjan; Pahari, Pallab; De, Saroj Ranjan Tetrahedron, 2007 , vol. 63, # 47 p. 11781 - 11792]
Efficient synthesis of anacardic acid analogues and their antibacterial activities
[Mamidyala, Sreeman K.; Ramu, Soumya; Huang, Johnny X.; Robertson, Avril A.B.; Cooper, Matthew A. Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 6 p. 1667 - 1670]
[Brimble, Margaret A.; Houghton, Scott I.; Woodgate, Paul D. Tetrahedron, 2007 , vol. 63, # 4 p. 880 - 887]
[Sinhababu, Achintya K.; Borchardt, Ronald T. Journal of Organic Chemistry, 1983 , vol. 48, # 14 p. 2356 - 2360]