20098-41-3

Usage

InChI:InChI=1/C10H6Cl4O4/c1-17-9(15)3-4(10(16)18-2)6(12)8(14)7(13)5(3)11/h1-2H3

Upstream product

• 34973-43-8 hexachloro-phthalide 
• 124-41-4 sodium methylate 
• 34973-35-8 Perchlor-4,5-dihydro-phthalsaeure-anhydrid 
• 34973-75-6 3,4,4,5,5,6-Hexachloro-cyclohexa-2,6-diene-1,2-dicarboxylic acid monomethyl ester 
• 67-56-1 methanol 
• 632-58-6 tetrachlorophthalic acid 
• 34973-71-2 Perchlor-bicyclo<4.2.0>octatrien-(1.5.7) 
• 74-88-4 methyl iodide 
• 90454-50-5 N-ethoxycarbonyl-(2,3,4,5-tetrachloro-1-thiophenio)amide 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 34973-77-8 3,4,4,5,5,6-Hexachloro-cyclohexa-2,6-diene-1,2-dicarboxylic acid dimethyl ester 
• 34973-78-9 1,3,4,4,5,6-Hexachloro-cyclohexa-2,5-diene-1,2-dicarboxylic acid dimethyl ester 
• 77-78-1 dimethyl sulfate 
• 560-42-9 1,4,5,6-tetrachloro-7,7-difluoro-norborna-2,5-diene-2,3-dicarboxylic acid dimethyl ester 

Relevant academic research and scientific papers

Unsymmetrically-Substituted 5,12-dihydrodibenzo[b,f][1,4]diazocine-6,11-dione Scaffold—A Useful Tool for Bioactive Molecules Design

Unsymmetrically N-substituted and N,N’-disubstituted 5,12-dihydrodibenzo [b,f][1,4]diazocine-6,11-diones were synthesized in the new protocol. The desired modifications of the dibenzodiazocine scaffold were introduced at the stages of proper selection of building blocks as well as post-cyclization modifications with alkylation or acylation agents, expanding the structural diversity and possible applications of synthesized molecules. The extension of developed method resulted in the synthesis of novel: tricyclic 5,10-dihydrobenzo[b]thieno[3,4-f][1,4]diazocine-4,11-dione scaffold and fused pentacyclic framework possessing two benzodiazocine rings within its structure. Additionally, the unprecedented rearrangement of 5,12-dihydrodibenzo[b,f][1,4]diazocine-6,11-diones to 2-(2-aminophenyl)isoindoline-1,3-diones was observed under the basic conditions in the presence of sodium hydride for secondary dilactams. The structures of nine synthesized products have been established by single-crystal X-ray diffraction analysis. Detailed crystallographic analysis of the investigated tri- and pentacyclic systems has shed more light on their structural features. One cell line derived from non-cancerous cells (EUFA30—human fibroblasts) and three tumor cells (U87—human primary glioblastoma, HeLa—cervix adenocarcinoma, BICR18—laryngeal squamous cell carcinoma) were used to determine the cytotoxic effect of the newly synthesized compounds. Although these compounds showed a relatively weak cytotoxic effect, the framework obtained for 5,12-dihydrodibenzo[b,f][1,4]diazocine-6,11-dione could serve as a convenient privilege structure for the design and development of novel bioactive molecules suitable for drug design, development and optimization programs.

Interaction of Thiophene S,N-Ylides with Dimethyl Acetylenedicarboxilate

The title reaction yields two products, dimethyl tetrachlorophthalate, by cycloaddition and dimethyl 2-chloro-3-ethoxycarbonylimino-2-trichlorothien-2-ylsuccinate by cycloaddition.The latter structure, verified by X-ray crystallography, corrects an earlier report.

Thiophene S,N-Ylides: A New Versatile Class of Sulphimides

Tetrachlorothiophene reacts with methyl, ethyl, and phenyl azidoformates and with toluene-p-sulphonyl azide at 130-150 deg C to give stable thiophene S,N-ylides. 2,5-Dichloro and 2,5-dibromo-thiophene and tetrabromothiophene yield products derived by nitrene attack at the α-position.The S,N-ylides undergo ready photolysis to liberate the parent nitrene, and react with a wide variety of electron-rich dienophiles as 4?-components to give tetrachlorodihydrobenzenes with extrusion of a thionitroso compound.With dienes the ylides react either as 2?- or 4?-systems.Thus with anthracene a dihydrothiophene analogue of triptycene is generated efficiently aromatised and de-ylidated with zinc in methanol.With dimethyl acetylenedicarboxylate the ylides yield a thiazocine by a novel ring expansion.Oxidation of the ylide system with 3-chloroperbenzoic acid gives the corresponding ylide S-oxide.Tetrachlorothiophene also reacts efficiently with diazoalkanes under rhodium acetate catalysis to give thiophene S,C-ylides, which undergo cycloaddition with nucleophilic alkenes much more slowly than their nitrogen analogues.

Polyhalogenated Bicycloocta-1,5,7-trienes, X. - Aromatizing Nucleophilic Substitutions and Rearrangements of Polyhalogenated 2,5-Diphenylbicycloocta-1,5,7-trienes

Nucleophilic reagents attack 1b-d on the four-membered ring with aromatization of the six-membered ring by elimination of chlorine.With methoxide di- and tetrasubstituted products 4a,b and 5b are formed, with thiolates however compounds 8, 9, 10, and 11 with 1, 2, and 4 substituents can be obtained.The reaction of 1b-d with primary amines leads to the diimines 12 or monoimines 13, while secondary amines cause ring opening to 16 or formation of the aminophthalides 20. - Cyclooctatetraene rearrangement of 1b and c in formic acid or in the presence of Ag+ -ions is complicated by the competing thermal rearrangement 1b,c -> 2b,c and numerous by-products. 3b and c were isolated only in 15 and 10percent yield, respectively.The mechanism of the nucleophilic substitutions is discussed.