145864-00-2Relevant academic research and scientific papers
1-Phenyl-1,2-benziodoxol-3-(1H)-one as Synthon for Phthalide Synthesis through Pd-Free, Base-Free, Sonogashira-Type Coupling Cyclization Reaction
Almasalma, Ahmad A.,Mejía, Esteban
, p. 188 - 195 (2017/11/30)
Hypervalent iodine(III) five-membered heterocycles have found broad application as atom-transfer reagents for organic synthesis. Among them, 1-phenyl-1,2-benziodoxol-3-(1H)-one is known as a traditional benzyne precursor, but no further synthetic applicat
Regioselective one-pot synthesis of isocoumarins and phthalides from 2-iodobenzoic acids and alkynes by temperature control
Kumar, Manian Rajesh,Irudayanathan, Francis Mariaraj,Moon, Joong Ho,Lee, Sunwoo
, p. 3221 - 3230 (2013/12/04)
Copper-catalyzed coupling reaction of 2-iodobenzoic acids and alkynes such as terminal acetylenes, alkynyl carboxylic acids, and trimethylsilylacetylene selectively afforded isocoumarins and phthalides in the presence of cesium carbonate (Cs2CO3) and dimethyl sulfoxide (DMSO). Among the regioselective products, only the 6-endo-dig product, isocoumarin, was formed at 100 °C, and the 5-exo-dig product, phthalide, was formed as a major product at 25 °C. A variety of alkynes produced the corresponding isocoumarins and phthalides in good yields. A mechanism is suggested in which the formation of 2-alkynylbenzoic acid as an intermediate via Sonogashira-type coupling was ruled out in the reaction pathway. Copyright
THE CHEMISTRY OF PHTALIDE-3-CARBOXYLIC ACID - I DECARBOXYLATION ON THE PRESENCE OF THE ALDEHYDES
Prager, Rolf H.,Schiesser, Carl H.
, p. 1517 - 1522 (2007/10/02)
The decarboxylation of phthalide-3-carboxylic acid (3-oxo-1,3-dihydroisobenzofuran-1-carboxylic acid) has been studied in the melt, in dimethylsulfoxide, and in the presence of aromatic aldehydes.The latter are efficiently trapped to produce mixtures of 3-arylidene-phthalides and 3-(arylhydroxymethyl)phthalides.Kinetic and other evidence supports the proposal that this reaction occurs in a tight cyclic transition state.
