37568-81-3Relevant academic research and scientific papers
Radical-mediated synthesis of 3,4-dihydroisocoumarins: total synthesis of hydrangenol
Mandal, Samir Kumar,Roy, Subhas Chandra
, p. 4131 - 4134 (2007)
A radically promoted synthesis of 3,4-dihydroisocoumarins has been achieved in moderate to good yields using titanocene(III) chloride (Cp2TiCl) as the radical initiator. The total synthesis of (±)-hydrangenol has been completed using this radical technology. Cp2TiCl was prepared in situ from commercially available titanocene dichloride (Cp2TiCl2) and Zn-dust in THF under argon.
A Photocatalytic Meerwein Approach to the Synthesis of Isochromanones and Isochromenones
Crespi, Stefano,J?ger, Stefanie,K?nig, Burkhard,Fagnoni, Maurizio
, p. 2147 - 2153 (2017/04/24)
A visible-light RuII photoredox Meerwein synthesis of isochromanones and isochromenones is described starting from diazonium salts of differently substituted anthranilic acids and various alkenes. This approach has allowed the reliable and effi
Copper-Catalyzed Oxidative Cyclization of Carboxylic Acids
Sathyamoorthi, Shyam,Du Bois
supporting information, p. 6308 - 6311 (2016/12/23)
A method for converting C-H to C-O bonds through oxidative cyclization of carboxylic acids to generate lactone products is described. The reaction employs catalytic amounts of Cu(OAc)2 and potassium persulfate as the terminal oxidant and is performed open to air in an aqueous acetic acid solvent system. Preliminary mechanistic studies suggest that substrate oxidation likely proceeds by sulfate radical anion and that the Cu catalyst has no influence on the product-determining step. These conclusions differ from related investigations that propose the intermediacy of a carboxylate radical.
Expeditious synthesis of 3,4-dihydroisocoumarins and phthalides using the Heck-Matsuda reaction
Da Penha, Eduardo T.,Forni, José Augusto,Biajoli, André F.P.,Correia, Carlos Roque D.
scheme or table, p. 6342 - 6345 (2011/12/21)
Several 3,4-dihydroisocoumarins and phthalides were synthesized by an effective Heck-Matsuda reaction involving an ortho carboxybenzenediazonium salt with a series of styrenes bearing electron donating and electron withdrawing groups, methylvinyl ketone,
Titanocene(III) chloride mediated radical-induced synthesis of 3,4-dihydroisocoumarins: synthesis of (±)-hydrangenol, (±)-phyllodulcin, (±)-macrophyllol and (±)-thunberginol G
Mandal, Samir Kumar,Roy, Subhas Chandra
experimental part, p. 11050 - 11057 (2009/04/11)
A radical-promoted synthesis of 3,4-dihydroisocoumarins has been achieved in moderate to good yields using titanocene(III) chloride (Cp2TiCl) as the radical initiator. The total synthesis of four naturally occurring dihydrocoumarins hydrangenol, phyllodulcin, macrophyllol and thunberginol G has been accomplished using the radical technology. Cp2TiCl was prepared in situ from commercially available titanocene dichloride (Cp2TiCl2) and Zn-dust in THF under argon.
A case of pictet-spengler revisited: Application to the synthesis of dihydroisocoumarins
Choukchou-Braham,Mostefa-Kara,Cheikh,Didi,Villemin
, p. 169 - 178 (2007/10/03)
The reaction of Pictet-Spengler was revisited, and its modified conditions were applied to develop a general methodology toward the synthesis of dihydroisocoumarins containing a no-electron rich aromatic ring.
Synthesis of 3-aryl- and 3-aryl-3,4-dihydroisocoumarins
Ahmad, Hafiz B.,Rama, Nasim H.,Hussain, Mazhar,Hussain, Muhammad T.,Qasim, Malik M.,Hameed, Shahid,Malana, Muhammad A.,Malik, Abdul
, p. 611 - 615 (2007/10/03)
The condensation of homophthalic acid 6 with the appropriate acid chlorides 7a-c yield the respective isocoumarins 8a-c, which are converted to keto-acids 9a-c by alkaline hydrolysis. The 3,4-dihydroisocoumarins 12a-c are obtained by reduction of the keto
Optional ortho and lateral lithiations of 4,4-dimethyl-2-(o-tolyl)oxazolines
Tahara, Naruki,Fukuda, Tsutomu,Iwao, Masatomo
, p. 9069 - 9072 (2007/10/03)
4,4-Dimethyl-2-(o-tolyl)oxazolines 1 undergo normal lateral lithiation at the benzylic position by treatment with sec-BuLi in diethyl ether at -78°C. In contrast, metalation of 1 with sec-BuLi/TMEDA in diethyl ether at the same temperature leads to ortho-
Oxidation of 3-arylisochromans by dimethyldioxirane. An easy route to substituted 3-arylisocoumarins
Bovicelli, Paolo,Lupattelli, Paolo,Crescenzi, Benedetta,Sanetti, Anna,Bernini, Roberta
, p. 14719 - 14728 (2007/10/03)
The selective oxidation of the two different benzylethereal position of 3-arylisochromans by dimethyldioxirane as a function of different substituents on the aromatic rings was studied. The easy oxidation of these compounds was exploited for a new easy ac
Convenient syntheses of 3-aryl-3,4-dihydroisocoumarins and lunularic acid derivatives
Mali, Raghao S.,Shelke, Dattatray W.
, p. 822 - 825 (2007/10/02)
A convenient two-step approach for the syntheses of 3-aryl-3,4-dihydroisocoumarins (13-17) including some naturally occurring 3-aryl-8-hydroxy-3,4-dihydroisocoumarins (1,2) and lunularic acid derivatives (18-21) is described from 2-formylbenzoic acids (4,
