135381-46-3Relevant articles and documents
Synthesis of phthalide derivatives using nickel-catalyzed cyclization of o-haloesters with aldehydes
Rayabarapu, Dinesh Kumar,Chang, Hong-Tai,Cheng, Chien-Hong
, p. 2991 - 2996 (2004)
The reaction of o-bromobenzoate (1b) with benzaldehyde (2a) in the presence of [NiBr2(dppe)] (dppe = 1,2-bis(diphenylphosphino)ethane) and zinc powder in THF (24 hours, reflux temperature), afforded 3-phenyl-3H- isobenzofuran-1-one (3a) in an 86% yield. Similarly, o-iodobenzoate reacts with 2a to give 3a, but in a lower yield (50%). A series of substituted aromatic and aliphatic aldehydes (2b, 4-MeC6H4CHO; 2c, 4-MeOC 6H4CHO; 2d, 3-MeOC6H4-CHO 2e, 2-MeOC6H4-CHO; 2f, 4-CNC6H4CHO; 2g, 4-(Me)3-CC6H4CHO; 2h, 4-C6H 4C6H4CHO; 2i, 4-ClC6H 4CHO; 2j, 4-CF3C6H4CHO; 2k, CH 3(CH2)5CHO; 21, CH3(CH 2)2-CHO) also underwent cyclization with o-bromobenzoate (1b) producing the corresponding phthalide derivatives in moderate to excellent yields and with high chemoselectivity. Like 1b, methyl 2-bromo-4,5- dimethoxybenzoate (1c) reacts with tolualdehyde (2b) to give the corresponding substituted phthalide 3m in a 71% yield. The methodology can be further applied to the synthesis of six-membered lactones. The reaction of methyl 2-(2-bromophenyl)acetate (1d) with benzaldehyde under similar reaction conditions afforded six-membered lactone 3o in a 68% yield. A possible catalytic mechanism for this cyclization is also proposed.
Efficient One-Pot Synthesis of 3-Substituted Phthalides via Additive Arylation of Organozinc Intermediate
Hasan, Mohsin,Tonk, Rajiv Kumar,Yadav, Vivek
, p. 783 - 789 (2022/02/17)
In recent years, substitution at the third position on phthalides has been proven a valua-ble synthetic intermediate for developing active molecules. We reported a direct and efficient one-pot method for the synthesis of 3-aryl Phthalides performed by adding organo-zinc reagent on methyl-2-formylbenzoate; reagent formed in-situ by the reaction between diethylzinc and different aryl boronic acid derivatives without using any ligand. The possible mechanism involved a coordi-nated zinc carbonyl transition state, arylation, and followed by the intramolecular cyclization. The substituents groups in boronic having different electronic and steric properties played an important role in the reaction completion time and yield. The structure elucidation and confirmation of the synthesized compounds were done by using H-NMR analytical data. The method can be useful for synthesizing various scaffolds and intermediates in search of potentially active compounds.
Ni(0)-Catalyzed Dimerization of o-Keto Carboxylic Acid Pseudochlorides
Yangirov,Fatykhov,Sedova,Gileva,Khafizova,Meshcheryakova,Khalilov,Kraikin
, p. 670 - 677 (2019/07/17)
A new protocol of the synthesis of 3,3′-diaryl-3,3′-diphthalides by dehalogenation of o-keto carboxylic acid pseudochlorides is implemented. The feature of the new protocol is that the reaction is carried out in the presence of a zero-valent nickel comple
