36157-40-1Relevant articles and documents
Synthesis, characterization and biological evaluation of new 4-Aryl-6-(2,5-dichlorothiophen-3-yl)-1,2-dihydro-2-oxopyridine-3-carbonitrile
Al-refai, Mahmoud
, p. 725 - 728 (2015)
Condensation of 3-acetyl-2,5-dichlorothiophene with different aldehydes in presence of ethyl cyanoacetate led to the formation of the new oxopyridine derivatives containing a thiophene moiety (3a-j) in high yields. All newly synthesized compounds were characterized by standard spectroscopic techniques. Antibacterial evaluation for all new compounds shows no activity against four different types of bacteria.
Structural Characterization of a New Chalcone Compound Containing a Thiophene Moiety: (E)-3-(5-Bromothiophen-2-YL)-1- (2,5-Dichlorothiophen-3-YL)-2-Propen-1-One
Delgado,Henao,Quintana,Al-Maqtari,Jamalis,Sirat
, p. 1440 - 1445 (2018)
The crystal structure of the new chalcone derivative (E)-3-(5-bromothiophen-2-yl)-1-(2,5-dichlorothiophen- 3-yl)-2-propen-1-one is synthesized and structurally characterized by spectroscopic IR, NMR, and HRMS techniques. Its crystal and molecular structure is determined from the single crystal X-ray diffractionstudy. This compound crystallizes in the monoclinic system and space group P21/n (N 19). The crystal packing is governed by C—H..O non-conventional hydrogen bond-type intermolecular interactions, forming extended zigzag chains related by 21 screw axes running along the [010] direction, with graph-set C(8). These hydrogen bonds contribute to the stabilization of the crystal structure that packs with an efficiency of 71.4%.
Facile synthesis of 2-(substituted amino)-4H-thieno[3,2-e]-1,3-thiazin-4- ones
Abu-El-Halawa, Rajab,Sarabi, Alaa,El-Abadelah, Mustafa M.
, p. 1251 - 1255 (2008)
Interaction between 2,5-dichlorothiophene-3-carbonyl isothiocyanate, accessible via 2,5-dichlorothiophene-3-carbonyl chloride, and model heterocyclic amines produced the respective 2,5-dichloro-N-(substituted aminocarbonothioyl) thiophene-3-carboxamides. Upon heating, the deprotonated form of the latter underwent intramolecular cyclization to deliver the corresponding 2-(substituted amino)-4H-thieno[3,2-e]-1,3-thiazin-4-ones. The structures of these new bicyclic derivatives and their acyclic precursors are based on microanalytical and spectral (IR, MS, and NMR) data.
Synthesis, Spectroscopic Characterization and X-ray Structure Analysis of 6-(2,5-Dichlorothiophen-3-yl)-2-methoxy-4-(4-methoxyphenyl)pyridine-3-carbonitrile
Al-Refai, Mahmoud,Ibrahim, Mohammad M.,Geyer, Armin,Marsch, Michael,Ali, Basem F.
, p. 331 - 340 (2016)
Abstract: The title compound was prepared by the condensation of an equimolar mixture of 1-(2,5-dichlorothiophen-3-yl)-3-(4-methoxyphenyl)prop-2-en-1-one, malononitrile and sodium hydroxide. The molecular structure was fully characterized using different spectroscopic methods. Mass ESI–HRMS measurements were performed. The HRESIMS analysis revealed the molecular formula, C18H12Cl2N2O2SNa, with [M?+?Na]+ and [M?+?Na?+?2]+ and [M?+?Na?+?4]+ isotopic clusters characteristic for a dichlorinated compound. The compound was also thoroughly characterized by 1H, 13C, NMR spectra and 2D NMR spectra (COSY, HSQC and HMBC). The molecular structure was confirmed by X-ray single crystal analysis. The new compound crystallizes in the orthorhombic, Pbcn space group with unit cell dimensions: a?=?31.901(7) ?, b?=?15.412(4) ?, c?=?7.3655(14) ?, V?=?3621.3(13) ?3 and Z?=?8. In the title compound, the central pyridine ring carries four substituents, a thiophene ring, a methoxyphenyl ring, a carbonitrile group and a methoxy group. The dihedral angles between the planes of the pyridine ring, the thiophene ring and the methoxyphenyl ring are 36.66 and 40.18°, respectively. Intermolecular C–H···O/N, π···π and anion···π [Cl···π] interactions are found in the crystal structure. All interactions consolidate a three dimensional network. Graphical Abstract: Synthesis, characterization, crystal, molecular structure, and crystal supramolecularity of 6-(2,5-dichlorothiophen-3-yl)-2-methoxy-4-(4-methoxyphenyl)pyridine-3-carbonitrile are reported. [Figure not available: see fulltext.]
Synthesis method of 3-acetyl-2,5-dichlorothiophene
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Paragraph 0032-0043, (2020/02/17)
The invention discloses a synthesis method of 3-acetyl-2,5-dichlorothiophene and belongs to the field of organic synthesis. 1-methyl-4-chlorobutenal is added to a methanol solution, sodium methoxide is added after cooling, after thioacetylchloride is dropwise added, and a heating reaction is conducted to obtain the 3-acetyl-2,5-dichlorothiophene. The synthesis method is simple and convenient to operate, is green and environmentally friendly in production, the yield of the obtained product is higher, and the synthesis method is more suitable for mass production.
The synthesis, characterization, cytotoxic activity assessment and structure-activity relationship of 4-aryl-6-(2,5-dichlorothiophen-3-yl)-2-methoxypyridine-3-carbonitriles
Al-Refai, Mahmoud,Ibrahim, Mohammad M.,Azmi, Mohamad Nurul,Osman, Hasnah,Bakar, Mohamad Hafizi Abu,Geyer, Armin
, (2019/11/20)
A series of 2-methoxypyridine-3-carbonitrile (5a-i)-bearing aryl substituents were successfully synthesized in good yields by the condensation of chalcones (4a-i) with malononitrile in basic medium. The condensation process, in most cases, offers a route to a variety of methoxypyridine derivatives (6a-g) as side products in poor yields. All new compounds were fully characterized using different spectroscopic methods. Mass ESI-HMRS measurements were also performed. Furthermore, these compounds were screened for their in vitro cytotoxicity activities against three cancer cell lines; namely, those of the liver (line HepG2), prostate (line DU145) and breast (line MBA-MB-231). The cytotoxicity assessment revealed that compounds 5d, 5g, 5h and 5i exhibit promising antiproliferative effects (IC50 1-5 μM) against those three cancer cell lines.
Synthesis, characterization and antimicrobial activity of new chalcones and their 6-aryl-4-(2,5-dichlorothiophen-3-yl)-6H-1,3-thiazin-2-amine derivatives
Al-Refai, Mahmoud,Ibrahim, Mohammad M.,Alsohaili, Sohail,Geyer, Armin
, p. 560 - 564 (2017/05/01)
Chalcones (5a-h) were prepared in high yields via the condensation of 3-acetyl-2,5-dichlorothiophene (3) with aryl aldehydes (4a-h). The reaction of the resulting chalcones with thiourea in the presence of a catalytic amount of hydrochloric acid provided the 1,3-thiazin-2-amine derivatives (6a-g) in moderate yields. All new compounds were characterized by extensive NMR analysis data, including 1D NMR experiments (1H and 13C) and 2D NMR experiments (COSY, HMBC, HSQC), as well as ESIMS and HRESIMS data. The newly synthesized compounds were evaluated for their biological activities, which demonstrate a very good to low bioactivities as antibacterial and antifungal, respectively.
CATALYTIC REDUCTIVE DEHALOGENATION OF THIOPHENE DERIVATIVES
Sharf, V. Z.,Taits, S. Z.,Gurovets, A. S.,Vol'kenshtein, Yu. B.,Fabrichnyi, B. P.,Shcherbakova, S. I.
, p. 130 - 133 (2007/10/02)
A method for the preparation of 3-substituted derivatives of thiophene by reductive dehalogenation of 2,5-dihalo-substituted thiophenes in the presence of a palladium complex is proposed.The dehalogenation reaction is a stepwise process.The presence of an acyl group in the 3 position increases the rate of the process.
