70010-47-8Relevant academic research and scientific papers
Hexafluoroisopropanol as solvent and promotor in the Paal-Knorr synthesis of N-substituted diaryl pyrroles
Schirmacher, Robert H.E.,R?sch, Daniel,Thomas, Franziska
, (2021/02/20)
An additive-free synthesis of challenging N-substituted aryl pyrroles from the often poorly soluble corresponding 1,4-diketones by means of the Paal-Knorr pyrrole synthesis is reported, which makes use of the unique properties of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as a solvent and reaction promotor. Our procedure offers simple execution and purification as well as easy scale-up and can be applied in the Paal-Knorr synthesis of a large number of structurally diverse pyrroles including the synthetically challenging tetra- and penta-substituted pyrroles in moderate to excellent yields. HFIP can also be used as solvent in the Paal-Knorr synthesis of furans and thiophenes; however, the solvent effect is more pronounced in synthesis of pyrroles.
Synthesis of heterocyclic compounds with adamantane-like cage structures consisting of phosphorus, sulfur, and carbon
Kutsumura, Noriki,Ohshita, Ryuichiro,Horiuchi, Jumpei,Tateno, Kotaro,Yamamoto, Naoshi,Saitoh, Tsuyoshi,Nagumo, Yasuyuki,Kawai, Hidetoshi,Nagase, Hiroshi
, p. 5214 - 5219 (2017/07/28)
The synthesis of novel adamantane-like cage compounds consisting of phosphorus, sulfur, and carbon atoms was developed. We examined the reaction of a variety of acetophenone derivatives with P4S10 in refluxing benzene. A novel noradamantane-like cage compound was also synthesized, when the reaction of 2’-methoxyacetophenone with P4S10 was performed in refluxing toluene. In addition, by using the adamantane-like cage compound, 4,4’-dimethoxybenzophenone and N,N-dimethylbenzamide were successfully transformed into the corresponding thioketone (98%) and benzothioamide (89%), respectively.
Environment-responsive multicolor fluorescent dyes based on nitrophenyl or nitrophenylethynyl oligothiophene derivatives: Correlation between fluorescence and π-conjugation length
Hachiya, Sojiro,Asai, Kengo,Konishi, Gen-Ichi
, p. 3317 - 3320 (2013/07/05)
We report the unique environment-responsive fluorescence of nitrophenyl or nitrophenylethynyl oligothiophene derivatives with different numbers of thiophene rings. With an increase in the number of thiophene rings, the maximum fluorescence quantum yield (
HCV NS5A replication complex inhibitors. Part 3
Lopez, Omar D.,Nguyen, Van N.,St. Laurent, Denis R.,Belema, Makonen,Serrano-Wu, Michael H.,Goodrich, Jason T.,Yang, Fukang,Qiu, Yuping,Ripka, Amy S.,Nower, Peter T.,Valera, Lourdes,Liu, Mengping,O'Boyle II, Donald R.,Sun, Jin-Hua,Fridell, Robert A.,Lemm, Julie A.,Gao, Min,Good, Andrew C.,Meanwell, Nicholas A.,Snyder, Lawrence B.
, p. 779 - 784 (2013/02/25)
In a recent disclosure,1 we described the discovery of dimeric, prolinamide-based NS5A replication complex inhibitors exhibiting excellent potency towards an HCV genotype 1b replicon. That disclosure dealt with the SAR exploration of the peripheral region of our lead chemotype, and herein is described the SAR uncovered from a complementary effort that focused on the central core region. From this effort, the contribution of the core region to the overall topology of the pharmacophore, primarily vector orientation and planarity, was determined, with a set of analogs exhibiting 50 in a genotype 1b replicon assay.
HEPATITIS C VIRUS INHIBITORS
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Page/Page column 275, (2011/07/30)
The present disclosure is generally directed to antiviral compounds, and more specifically directed to compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such compounds, and methods for inhibiting the function of the NS5A protein
One-pot double suzuki- miyaura couplings: Rapid access to nonsymmetrical tri(hetero)aryl derivatives
Beaumard, Floriane,Dauban, Philippe,Dodd, Robert H.
supporting information; experimental part, p. 1801 - 1804 (2009/08/15)
We describe a one-pot, simultaneous Suzuki- Miyaura cross-coupling of two different aryl boronic acids with symmetrical dibromo aryl and heterocyclic substrates to give as major products the unsymmetrical disubstituted tri(hetero)aryl derivatives. Yields
Synthesis and antiparasitic evaluation of bis-2,5-[4-guanidinophenyl]thiophenes
Gonzalez, Jose L.,Stephens, Chad E.,Wenzler, Tanja,Brun, Reto,Tanious, Farial A.,Wilson, W. David,Barszcz, Todd,Werbovetz, Karl A.,Boykin, David W.
, p. 552 - 557 (2008/02/11)
A series of bis-2,5-[4-guanidinophenyl]thiophenes were prepared in a five step process starting from 2,5-bis[trimethylstannyl]thiophene. The compounds were evaluated in vitro against Trypanosoma brucei rhodesiense (T. b. r.), Plasmodium falciparum (P. f.)
Design, synthesis, and structure-activity relationship of novel thiophene derivatives for β-amyloid plaque imaging
Chandra, Rajesh,Kung, Mei-Ping,Kung, Hank F.
, p. 1350 - 1352 (2007/10/03)
Novel 2,5-diphenylthiophene derivatives were synthesized and structure activity relationship with regard to Aβ plaque binding was studied. Binding affinities of these compounds were found to range from 3.9 to >1000 nM, depending on the substitution patter
Synthesis of α-Thiophene Oligomers via Organotin Compounds
Kamal, Marwan R.,Al-Taweel, Samir A.,El-Abadelah, Mustafa M.,Ajaj, Khalid M. Abu
, p. 65 - 74 (2007/10/03)
A versatile synthetic route involving the use of organotin compounds has been applied for the preparation of functionalized oligothiophenes.Thus, substituted α-bithiophenes have been synthesized via the coupling reaction of 2-bromothiophenes with 2-trimethylstannylthiophene.The latter reagent couples with 2,5-dibromothiophenes to give the α-terthiophenes which are also accessible through the reaction of 5-trimethylstannyl-α-bithiophene with 2-bromothiophenes. 2,5-Bis(trimethylstannyl)thiophene and 5,5'-bis(trimethylstannyl)-α-bithiophene react with 2-bromothiophenes to give α-terthiophenes and α-quaterthiophenes, respectively. α-Quaterthiophene is also produced via the reaction of 5-trimethylstannylthiophene with 5,5'-dibromo-α-bithiophene.The coupling reaction of 5-trimethylstannyl-α-bithiophene with 2,5-dibromothiophene affords the α-quinquethiophene.The structures of the new compounds were confirmed by elemental analysis, Mass spectrometry, 1H- and 13C-NMR spectral data.Keywords: Functionalized α-thiophene oligomers; synthesis; 2-stannylthiophenes
Models for intramolecular exchange in organic π-conjugated open-shell systems: 3-Nitrenophenyl and 4-nitrenophenyl units connected by 2,5-furandiyl, 2,5-thiophenediyl, and 2,5-pyrrolediyl nonalternant exchange linkers
Ling, Chris,Lahti, Paul M.
, p. 8784 - 8792 (2007/10/02)
The first bis(arylnitrenes) linked by heterocyclic pseudoaromatic rings were generated in a glassy, 77 K 2-methyltetrahydrofuran matrix by photolysis at wavelengths >300 nm: 2,5-bis(3-nitrenophenyl)furan (1); 2,5-bis-(3-nitrenophenyl)thiophene (2); 2,5-bi
