69338-59-6Relevant academic research and scientific papers
Synthesis of tetrahydrophthalazine and phthalamide (phthalimide) derivatives via palladium-catalysed carbonylation of iodoarenes
Marosv?lgyi-Haskó, Diána,Petz, Andrea,Takács, Attila,Kollár, László
experimental part, p. 9122 - 9128 (2011/12/02)
1,2,3,4-Tetrahydrophthalazin-1-one and 1,2,3,4-tetrahydrophthalazin-1,4- dione derivatives were synthesised in high (up to 85%) and low yields using 2-iodobenzyl bromide and 1,2-diiodobenzene as bifunctional substrates, respectively. Iodoarenes, carbon monoxide and various hydrazine derivatives as N-nucleophiles were used in a three-component palladium-catalysed cascade hydrazinocarbonylation. A similar palladium-catalysed reaction, the aminocarbonylation of 1,2-diiodobenzene, resulted mainly in the formation of two types of major products depending on the amine N-nucleophiles: the use of primary amines yielded N-substituted phthalimides in double carbonylation, while secondary amines react with one of the iodoarene functionalities affording the corresponding 2-iodobenzamides. Due to double carbon monoxide insertion at one or both iodoarene functionalities, ketocarboxamide-carboxamide or bis-ketocarboxamide derivatives could be isolated by the modification of the reaction conditions. Some mechanistic details of the ring-closure reactions and the conditions leading to side-products are also discussed.
The reaction of phthalidylidene dichloride with primary amines. Synthesis and X-ray molecular structure of N-substituted phthalisoimides
Guirado, Antonio,Zapata, Andres,Ramirez De Arellano, M. Carmen
, p. 5305 - 5324 (2007/10/03)
An efficient method for the synthesis of N-substituted phthalisoimides, by reaction of phthalidylidene dichloride with primary amines, is described. The reactions with arylamines, arylenediamincs and alkylenediamines lead to the corresponding phthalisoimides or bisphthalisoimides in nearly quantitative yields. However, the reactions with alkylamines are not useful because of the relatively high nucleophilicity of alkylamines. Certain particular behaviours of arylamines, associated with the presence of specific ortho-substituents have been found. The reactions of arylamines bearing an o-hydroxymethyl group provide a convenient method for preparing 2-benzoxazinylbenzoic acids. The X-ray crystallographic structures of N-(2-methoxyphenyl)phthalisoimide 3a and 2-(4H-3.1-benzoxazin-2-yl)benzoic acid 15a have been determined.
SONOCHEMICAL BARBIER REACTION WITH ISOCYANATES AND THE SYNTHETIC USE OF THE ORGANOMETALLIC INTERMEDIATE
Einhorn, J.,Luche, J. L.
, p. 501 - 504 (2007/10/02)
Sonication of aryl halides, t-butyl isocyanate and sodium in THF leads to an organosodium intermediate which is easily and regioselectively ortho-lithiated and reacted with electrophilic reagents.
FEATURES OF THE REACTION OF PHTHALOYL CHLORIDE WITH PRIMARY AMINES
Ganin, E. V.,Makarov, V. F.,Rozynov, B. V.
, p. 1772 - 1777 (2007/10/02)
The reaction of phthaloyl chloride with primary amines, which leads to the formation of the N,N'-substituted diamides of phthalic acid, takes place through the intermediate formation of the N-substituted isophthalimides.The reactivity of these compounds i
