22230-21-3Relevant academic research and scientific papers
Pd-Catalyzed C(sp2)-H aminocarbonylation using the Langlois reagent as a carbonyl source
Li, Xiao-Fang,Shi, Lin-Feng,Zhang, Xing-Guo,Zhang, Xiao-Hong
, p. 6438 - 6442 (2018)
A Pd-catalyzed C(sp2)-H aminocarbonylation of aryl carboxamides assisted by an N,S-bidentate directing group was developed, in which cheap and stable sodium trifluoromethanesulfinate was first utilized as a carbonyl source. The reaction can be applicable to a wide range of carboxamides with good functional group tolerance and afford isoindole-1,3-diones in moderate to good yields.
Copper-Mediated Cyanation of Aryl C—H Bond with Removable Bidenate Auxiliary Using Acetonitrile as the Cyano Source
Yu, Zhengwei,Zhang, Saisai,Shen, Zengming
, p. 1139 - 1142 (2018/10/15)
Copper-mediated cyanation of aryl C—H bond with removable bidenate auxiliary as a directing group has been developed, in which green and cheap acetonitrile is used as the “CN” source. By switching the reaction conditions, the C—H cyanated products and N-Ar-phthalimides can be provided in acceptable yields with high chemoselectivity, respectively. The use of quaternary ammonium salt is essential for cyanation reaction.
Preparation method of N-(2-methylthiophenyl)isoindole-1,3-diketone compound
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Paragraph 0022; 0041; 0042; 0043; 0044; 0045; 0046; 0047, (2018/07/30)
The invention discloses a preparation method of an N-(2-methylthiophenyl)isoindole-1,3-diketone compound. The preparation method comprises the following steps: by taking N-(2-methylthiophenyl)benzamide as a substrate; adding sodium trifluoromethanesulfinate into the substrate as a carbonyl source; adding a catalyst and carrying out stirred reaction in a reaction solvent for 24h under normal pressure and at 120 DEG C; after reaction is finished, filtering a reaction solution to obtain filtrate; concentrating the filtrate and removing the solvent by utilizing the rotary evaporator, so as to obtain residues; carrying out chromatography on the residues through a silica gel column; eluting through an eluting solution and collecting effluent liquid according to an actual gradient; combining theeffluent liquid containing a product, concentrating the combined effluent liquid and removing the solvent; finally, drying in vacuum to obtain a target product. The preparation method disclosed by theinvention has the advantages of simple preparation technology, less pollution, low energy consumption and high yield.
π-aromatic and sulfur nucleophilic partners in cationic π-cyclizations: Intramolecular amidoalkylation and thioamidoalkylation cyclization via ω-carbinol lactams
Hucher,Decroix,Daich
, p. 4695 - 4703 (2007/10/03)
NaBH4 reduction of imides 1 and 6a,b,c followed by a π-cyclization of the resultant N-acyliminium ions, generated in trifluoroacetic acid conditions, afforded two positional isomers, isoindolobenzothiazolinones 4 and 8, respectively. These ring closures proceeded via an intramolecular α-amidoalkylation with the classical α-aromatic or the atypical sulfur atom as an internal nucleophile. A ready access to the related six-membered N,S-heterocyclic compounds such as isoindolobenzothiazinones 20a and 21a is also described. During this reaction, we have shown that ω-carbinol lactam precursor 14a led to endocyclic and exocyclic N-acyliminium ions 18a and 19a in equilibrium via the cyclic aza-sulfonium ion A. The latter furnished the expected products 20a and 21a in good yields. Similarly, different ω-carbinol lactams 14b-e substituted at C-angular position afforded the corresponding isoindolobenzothiazinones 20b-e and 21b-e bearing an angular alkyl, aralkyl, or aryl group. In the case of methyl 14b and benzyl 14e groups, an additional amount of the dehydration products 16b and 31 was isolated. These results indicate that the isomerization-π-cyclization takes place via the cleavage of the thioether linkage in acidic medium.
