cas 17721-06-1, 3-AMINOTHIOPHENE | Articles data

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Synthesis of Thieno[3,2-e][1,4]diazepin-2-ones: Application of an Uncatalysed Pictet-Spengler Reaction
A series of 5-substituted thieno[3,2-e][1,4]diazepin-2-ones was synthesized in four steps from methyl 3-aminothiophene-2-carboxylate. After the coupling of 3-aminothiophene with α-amino acids, the key final step that involves an uncatalysed Pictet-Spengler reaction allowed the cyclization of the seven-membered diazepinone ring. The reaction was first optimized and then exemplified in three different series (phenylalanine, alanine and proline) that led to 24 target diazepinones, which includes 19 optically pure diastereomers. A new synthetic approach that uses an uncatalysed Pictet-Spengler cyclization reaction has been developed to access [3,2-e]-type fused thienodiazepinones.
Denoyelle, Séverine,Tambutet, Guillaume,Masurier, Nicolas,Maillard, Ludovic T.,Martinez, Jean,Lisowski, Vincent
p. 7146 - 7153
(2015)
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An easy synthesis of 3-amino- and 3-nitrothiophene
3-Amino- and 3-nitrothiophene are readily made by the decarboxylation of the corresponding thiophene-2-carboxylic acids which are easily prepared from the commercially available methyl 3-aminothiophene-2-carboxylate.
Barker,Huddleston,Wood
p. 3729 - 3734
(1995)
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Synthesis and evaluation of anticonvulsant activities of 7-phenyl-4,5,6,7-tetrahydrothieno[3,2-b]pyridine derivatives
A series of 7-phenyl-4,5,6,7-tetrahydrothieno[3,2-b]pyridine derivatives containing triazole and other heterocycle substituents (methyltriazole, tetrazole, and triazolone) is described. Two experimental methods, maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ), were used to evaluate the anticonvulsant activity of the target compounds. Moreover, the neurotoxicity (NT) was tested using the Rotarod test. 5-(4-Chlorophenyl)-4,5-dihydrothieno[2,3-e][1,2,4]triazolo[4,3-a]pyridine (6c) showed the best anticonvulsant activity. In the MES and PTZ experiments, the 50% effective dose (ED50) values of compound 6c were 9.5 and 20.5 mg/kg, respectively. From the therapeutic index (PI) values, 6c (MES and PTZ with PI values of 48.0 and 22.2, respectively) showed better safety than the clinical drugs carbamazepine (MES with PI value of 6.4) and ethosuximide (PTZ with PI value of 3.2). The biological activities of the compounds were verified by using molecular docking studies. Compound 6c showed significant interactions with residues at the benzodiazepine-binding site on gamma-aminobutyric acid A (GABAA) receptors. The results of in vivo GABA estimation and bicuculline-induced seizures showed that 6c may have an effect on the GABA system. The physicochemical and pharmacokinetic properties of the target compounds were predicted.
Wang, Shiben,Liu, Hui,Wang, Xuekun,Lei, Kang,Li, Guangyong,Li, Xiaojing,Wei, Lichao,Quan, Zheshan
(2019)
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Porous polymeric ligand promoted copper-catalyzed C-N coupling of (hetero)aryl chlorides under visible-light irradiation
A porous polymeric ligand (PPL) has been synthesized and complexed with copper to generate a heterogeneous catalyst (Cu@PPL) that has facilitated the efficient C-N coupling with various (hetero)aryl chlorides under mild conditions of visible-light irradiation at 80 °C (58 examples, up to 99% yields). This method could be applied to both aqueous ammonia and substituted amines, and is compatible to a variety of functional groups and heterocycles, as well as allows tandem C-N couplings with conjunctive dihalides. Furthermore, the heterogeneous characteristic of Cu@PPL has enabled a straightforward catalyst separation in multiple times of recycling with negligible catalytic efficiency loss by simple filtration, affording reaction mixtures containing less than 1 ppm of Cu residue. [Figure not available: see fulltext.]
Wang, Erfei,Chen, Kaixuan,Chen, Yinan,Zhang, Jiawei,Lin, Xinrong,Chen, Mao
p. 17 - 21
(2020/11/04)

Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction
The invention provides a ligand compound capable of being used for copper catalyzed aryl halide coupling reaction, the ligand compound is a three-class compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group, and the invention also provides a catalytic system for the aryl halide coupling reaction. Thecatalytic system comprises a copper catalyst, a compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group adopted as a ligand, alkali and a solvent, and meanwhile, the invention also provides a system for the aryl halide coupling reaction adopting the catalyst system. The compound containing the 2-(substituted or non-substituted) aminopyridine nitrogen oxygen group can be used as the ligand for the copper catalyzed aryl chloride coupling reaction, and the ligand is stable under a strong alkaline condition and can well maintain catalytic activity when being used for the copper-catalyzed aryl chloride coupling reaction. In addition, the copper catalyst adopting the compound as the ligand can particularly effectively promote coupling of copper catalyzed aryl chloride and various nucleophilic reagents which are difficult to generate under conventional conditions, C-N, C-O and C-S bonds are generated, and numerous useful small molecule compounds are synthesized. Therefore, the aryl halide coupling reaction has a very good large-scale application prospect by adopting the copper catalysis system of the ligand.
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Paragraph 0111-0118; 0120

(2021/05/29)

Design, synthesis and biological evaluation of novel N-sulfonylamidine-based derivatives as c-Met inhibitors via Cu-catalyzed three-component reaction
In our continuing efforts to develop novel c-Met inhibitors as potential anticancer candidates, a series of new N-sulfonylamidine derivatives were designed, synthesized via Cu-catalyzed multicomponent reaction (MCR) as the key step, and evaluated for their in vitro biological activities against c-Met kinase and four cancer cell lines (A549, HT-29, MKN-45 and MDA-MB-231). Most of the target compounds showed moderate to significant potency at both the enzyme-based and cell-based assay and possessed selectivity for A549 and HT-29 cancer cell lines. The preliminary SAR studies demonstrated that compound 26af (c-Met IC50 = 2.89 nM) was the most promising compound compared with the positive foretinib, which exhibited the remarkable antiproliferative activities, with IC50 values ranging from 0.28 to 0.72 μM. Mechanistic studies of 26af showed the anticancer activity was closely related to the blocking phosphorylation of c-Met, leading to cell cycle arresting at G2/M phase and apoptosis of A549 cells by a concentration-dependent manner. The promising compound 26af was further identified as a relatively selective inhibitor of c-Met kinase, which also possessed an acceptable safety profile and favorable pharmacokinetic properties in BALB/c mouse. The favorable drug-likeness of 26af suggested that N-sulfonylamidines may be used as a promising scaffold for antitumor drug development. Additionally, the docking study and molecular dynamics simulations of 26af revealed a common mode of interaction with the binding site of c-Met. These positive results indicated that compound 26af is a potential anti-cancer candidate for clinical trials, and deserves further development as a selective c-Met inhibitor.
Fang, Sen-Biao,Li, Hui-Jing,Nan, Xiang,Wu, Rui,Wu, Yan-Chao,Zhang, Jing,Zhang, Zhi-Zhou
(2020/06/04)

A new ligand for copper-catalyzed amination of aryl halides to primary(hetero)aryl amines
N,N′-Bis(3,5-dimethoxyphenyl)cyclopentane-1,1-dicarboxamide was found as a new ligand for copper-catalyzed amination of aryl iodides, bromides and chlorides to afford various primary (hetero)aryl amines. These reactions proceeded efficiently under mild conditions when inexpensive aqueous ammonia (28% NH3 in H2O) was used as the amino source.
Chen, Dong,Dong, Xinrui,Jiang, Shang,Jiang, Sheng,Qiu, Yatao,Wu, Xiaoxing
supporting information

(2020/02/11)

Photochemical synthesis method of heteroarylamine compounds
The invention provides a photochemical synthesis method of heteroarylamine compounds. The photochemical synthesis method comprises the following steps: S1, mixing raw materials including heteroaryl nitro compounds, a solvent and a photocatalyst to obtain a mixture; and S2, carrying out a photocatalytic reduction reaction on the mixture under an illumination condition to obtain a product system containing the heteroarylamine compounds. According to the photochemical synthesis method, photocatalytic reduction of various different heteroaryl nitro compounds is achieved under the illumination condition, and the high-yield heteroaryl amine compounds are obtained. The photocatalyst is an existing common catalyst, has no strict requirements on equipment and is easy to recover, and the safety riskof the heteroarylamine compound and the catalyst cost are reduced. Any metal reagent and reducing agent do not need to be added in the whole reaction process of photocatalysis, the reaction conversion rate is high, and post-treatment is simple and easy to operate, so the method is safer and more environmentally friendly.
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Paragraph 0070

(2020/10/14)

Sonication and Microwave-Assisted Primary Amination of Potassium- Aryltrifluoroborates and Phenylboronic Acids under Metal-Free Conditions
The transition-metal-free generation of a series of primary arylamines from potassium aryltrifluoroborates and phenylboronic acids- is reported. The method uses a mild, inexpensive source of nitrogen (hydroxylamine-O-sulfonic acid) in cooperation with aqueous sodium hydroxide in acetonitrile. Both a sonication and a microwave-assisted method were developed, which are capable of converting ArBF3K functionalities into primary arylamines (ArNH2) in isolated yields of up to 78% (10 examples for each method). This report represents the first general method for the conversion of aryltrifluoroborates into primary arylamines under mild, transition-metal-free conditions in moderate to very good yields. The method is applicable to a wide array of substrates containing electron-donating, electron-neutral, or electron-withdrawing substituents. Both the sonication and microwave methods were also applied to the generation of anilines from phenylboronic acids in isolated yields of up to 96% (12 examples for each method) that were superior to existing room temperature methods in terms of yield, while also offering much shorter reaction times (15 min vs 16 h). In particular, the microwave method is the first to allow for the conversion of arylboronic acids containing strongly electron-withdrawing substituents into the corresponding anilines in good yields, along with electron-donating- substituents in very good to excellent yields.
Kuik, Dale,McCubbin, J. Adam,Tranmer, Geoffrey K.
p. 2555 - 2561
(2017/05/22)

Polysubstituted quinolone compounds, and preparation method and use thereof
The invention provides polysubstituted quinolone compounds, and a preparation method and a use thereof, and concretely provides a polysubstituted quinolone compound represented by formula I, and optical isomers, pharmaceutically acceptable salts or solvates thereof. All groups in the formula I are defined in the description. The quinolone compound has excellent c-Met inhibition activity, and can be used for treating c-Met activity or expression level corrected diseases.
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Paragraph 0252; 0253; 0254

(2017/09/19)

SUBSTITUTED IMIDAZO[1,2-b]PYRIDAZINES, SUBSTITUTED IMIDAZO[1,5-b]PYRIDAZINES, RELATED COMPOUNDS, AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS
The invention provides substituted imidazo[1,2-b]pyridazine compounds, substituted imidazo[1,5-b]pyridazine compounds, related compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat medical disorders, e.g., Gaucher disease, Parkinson's disease, Lewy body disease, dementia, or multiple system atrophy, in a patient. Exemplary substituted imidazo[1,2-b]pyridazine compounds described herein include substituted imidazo[1,2-b]pyridazine-3-carboxamide compounds and variants thereof.
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Paragraph 00266

(2017/12/14)

Thiophene/thiazole-benzene replacement on guanidine derivatives targeting α2-Adrenoceptors
Searching for improved antagonists of α2-adrenoceptors, a thorough theoretical study comparing the aromaticity of phenyl-, pyridinyl-, thiophenyl- and thiazolylguanidinium derivatives has been carried out [at M06-2X/6–311++G(p,d) computational level] confirming that thiophene and thiazole will be good ‘ring equivalents’ to benzene in these guanidinium systems. Based on these results, a small but chemically diverse library of guanidine derivatives (15 thiophenes and 2 thiazoles) were synthesised to explore the effect that the bioisosteric change has on affinity and activity at α2-adrenoceptors in comparison with our previously studied phenyl derivatives. All compounds were tested for their α2-adrenoceptor affinity and unsubstituted guanidinothiophenes displayed the strongest affinities in the same range as the phenyl analogues. In the case of cycloakyl systems, thiophenes with 6-membered rings showed the largest affinities, while for the thiazoles the 5-membered analogue presented the strongest affinity. From all the compounds tested for noradrenergic activity, only one compound exhibited agonistic activity, while two compounds showed very promising antagonism of α2-adrenoceptors.
Flood, Aoife,Trujillo, Cristina,Sanchez-Sanz, Goar,Kelly, Brendan,Muguruza, Carolina,Callado, Luis F.,Rozas, Isabel
p. 38 - 50
(2017/06/23)

Substituted 1,2,3,4-tetrahydrobenzo[C][2,7] naphthyridines and derivatives thereof as kinase inhibitors
The present invention relates to organic molecules capable of modulating tyrosine kinase signal transduction in order to regulate, modulate and/or inhibit abnormal cell proliferation.
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Page/Page column 45-46

(2016/03/06)

INHIBITORS TARGETING DRUG-RESISTANT INFLUENZA A
Provided are compounds according to formula (la) or (lb) as described herein, that are capable of modulating the activity of influenza viruses (e.g., influenza A virus), for example, via interaction with the M2 transmembrane protein, and other similar viroporins. Also provided are methods for treating an influenza A-affected disease state or infection comprising administering a composition comprising one or more compounds according to according to formulas (la') or (lb), as described herein.
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Paragraph 0512

(2013/06/27)

Ligandless copper-catalyzed coupling of heteroaryl bromides with gaseous ammonia
A range of different N- and S-containing heterocyclic bromides can be efficiently coupled with gaseous ammonia in the presence of copper(II) acetylacetonate [Cu(acac)2] as catalyst and in the absence of additional ligands. Unstable aminothiophenes and aminobenzothiophenes can be further reacted in situ to afford functionalized derivatives. Copyright
Fantasia, Serena,Windisch, Johannes,Scalone, Michelangelo
supporting information
p. 627 - 631
(2013/04/11)

ANTI-INFLAMMATORY COMPOUND HAVING INHIBITORY ACTIVITY AGAINST MULTIPLE TYROSINE KINASES AND PHARMACEUTICAL COMPOSITION CONTAINING SAME
The present invention is for the anti-inflammatory compounds that have an inhibitory activity against protein tyrosine kinases and their pharmaceutical composition(s) containing the compound as the active ingredient. Since the compounds of the present invention can inhibit multiple protein kinases associated with inflammatory diseases and immune disorders, they are useful for their prevention or treatment.
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Paragraph 0281-0283

(2013/03/28)

A practical synthesis of biaryls via a thermal decarboxylative Pd-catalyzed cross-coupling reaction operating at moderate temperature
The palladium-catalyzed decarboxylative cross-coupling of aminothiophene carboxylate and 1-bromo-4-chlorobenzene to produce 3-amino-2-(4-chlorophenyl) thiophene (2) is described. The cross-coupling proceeds under relatively mild conditions using catalytic Pd(0) and TBAB. Through use of a mixed-solvent system of DMF and NMP, it was possible to operate the cross-coupling system at 80 °C. An assessment of carbon dioxide liberation, which provides insight into the reaction operating parameters, is also discussed.
Mitchell, David,Coppert, David M.,Moynihan, Humphrey A.,Lorenz, Kurt T.,Kissane, Marie,McNamara, Orla A.,Maguire, Anita R.
scheme or table
p. 981 - 985
(2011/12/15)

An efficient copper-catalyzed synthesis of anilines by employing aqueous ammonia
Under the catalysis of CuI/2-carboxylic acid-quinoline-N-oxide, the cross coupling reactions between aryl iodides or bromides and aqueous ammonia proceed very well to afford N-unprotected aniline derivatives in excellent yields. This inexpensive catalytic system shows great functional group tolerance and excellent reaction selectivity. The Royal Society of Chemistry 2011.
Zeng, Xin,Huang, Wenming,Qiu, Yatao,Jiang, Sheng
supporting information; experimental part
p. 8224 - 8227
(2012/04/04)

Efficient copper-catalyzed direct amination of aryl halides using aqueous ammonia in water
The N2,N2′-diisopropyloxalohydrazide/CuO system efficiently catalyzed the direct amination of aryl bromides andiodides with aqueous ammonia in water at 60 °C in 24 h or at 120 °C in only 20-30 min. Both activated and unactivated aryl and heteroaryl bromides and iodides were readily aminated in good to excellent yields. A highly efficient N 2,N2′-diisopropyloxalohydrazide/CuO system was developed for the direct amination of aryl halides with aqueous ammonia in water at 60 °C for24 h or at 120 °C for 20-30 min. The resulting aromatic primary amines were obtained in good to excellent yields.
Meng, Fei,Zhu, Xinhai,Li, Ying,Xie, Jianwei,Wang, Bo,Yao, Junhua,Wan, Yiqian
supporting information; experimental part
p. 6149 - 6152
(2010/12/29)

New R/S-3,4-dihydro-2,2-dimethyl-2H-1-benzopyrans as KATP channel openers: Modulation of the 4-position
The present work aimed at exploring a series of diversely 4-arylthiourea-substituted R/S-3,4-dihydro-2,2-dimethyl-6-halo-2H-1-benzopyrans structurally related to (±)-cromakalim. These new compounds were examined in vitro as putative potassium channel openers (PCOs) on rat pancreatic islets (inhibition of insulin release) as well as on rat aorta rings (relaxation of aorta ring) and their activity was compared to that of the reference KATP channel activators (±)-cromakalim, (±)-pinacidil, diazoxide and of previously reported cromakalim analogues. Structure-activity relationships indicated that the most pronounced inhibitory activity on the insulin secretory process was obtained with molecules bearing a strong meta- or para-electron-withdrawing group (CN or NO2) on the phenyl ring of the arylthiourea moiety at the 4-position of the benzopyran nucleus (compounds 12-23). Among those, R/S-6-chloro-4-(4-cyanophenylaminothiocarbonylamino)-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran (16) was found to be the most potent benzopyran-type inhibitor of insulin release ever described. Most of these original benzopyran derivatives show increased selectivity for pancreatic versus vascular tissue. Radioisotopic investigations indicated that these new compounds activated pancreatic KATP channels.
Florence, Xavier,Sebille, Sophie,Tullio, Pascal de,Lebrun, Philippe,Pirotte, Bernard
experimental part
p. 7723 - 7731
(2010/03/04)

2-[3H-THIAZOL-2-YLIDINEMETHYL]PYRIDINES AND RELATED COMPOUNDS AND THEIR USE
The present invention pertains to certain 2-[3H-thiazol-2-ylidinemethyl]pyridine compounds and analogs thereof, which, inter alia, inhibit cell proliferation, treat cancer, etc., and more specifically to compounds of the following formula, wherein RA1, RA2, RA3, RA4, RB1, RB2, RNA, RNB, and X? are as defined herein: The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit cell proliferation, and in the treatment of proliferative conditions such as cancer, etc.
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Page/Page column 44

(2009/10/06)

An efficient copper-catalyzed amination of aryl halides by aqueous ammonia
The copper(I) bromide/1-(5,6,7,8-tetrahydroquinolin-8-yl)-2-methylpropan-l- one (CuBr-LS) combination catalyzed the cross-coupling reactions between aryl or heteroaryl halides and aqueous ammonia with high yields to produce primary aromatic or heteroaromatic amines at room temperature or under mild conditions.
Wang, Deping,Cai, Qian,Ding, Ke
supporting information; experimental part
p. 1722 - 1726
(2011/02/25)

2-ALKENYL-3-AMINOTHIOPHENE DERIVATIVE AND METHOD FOR PRODUCING THE SAME
Disclosed is a method for commercially producing 2-alkenyl-3-aminothiophene derivatives, which are useful as intermediates for agricultural chemicals, at low cost. Specifically disclosed is a method for introducing alkenyl groups into the 2-position of 3-aminothiophene derivatives by reacting 3-aminothiophene derivatives represented by the general formula (2) below or salts thereof with a ketone represented by the general formula (1) below without using a protecting group. Also specifically disclosed are 2-alkenyl-3-aminothiophene derivatives (3a) to (3d) which are useful as intermediates for agricultural chemicals,
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Page/Page column 10-11

(2009/01/24)

MODULATORS OF CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR
The present invention relates to modulators of ATP-B inding Cassette ("ABC") transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator, compositions thereof, and methods therewith. The present invention also relates to methods of treating ABC transporter mediated diseases using such modulators
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Page/Page column 49-50

(2009/01/20)

Cross-coupling of aryl/heteroaryl bromides with ammonia using a copper-carbene catalyst
A variety of aryl and heteroaryl bromides were cross-coupled with ammonia in good to high yields in the presence of a copper-NHC catalyst. The Royal Society of Chemistry.
Ntaganda, Rukundo,Dhudshia, Bhartesh,Macdonald, Charles L. B.,Thadani, Avinash N.
supporting information; experimental part
p. 6200 - 6202
(2009/05/06)

Ammonium salts as an inexpensive and convenient nitrogen source in the Cu-catalyzed amination of aryl halides at room temperature
Convenient and inexpensive ammonium salts such as NH4Cl and aqueous NH3 solution are found to be readily utilized in the Cu-catalyzed room temperature N-arylation of aryl halides, providing N-unprotected aniline derivatives in high yields. The Royal Society of Chemistry.
Kim, Jinho,Chang, Sukbok
supporting information; scheme or table
p. 3052 - 3054
(2009/02/04)

Structure-activity relationships in the binding of chemically derivatized CD4 to gp120 from human immunodeficiency virus
The first step in HIV infection is the binding of the envelope glycoprotein gp120 to the host cell receptor CD4. An interfacial "Phe43 cavity" in gp120, adjacent to residue Phe43 of gp120-bound CD4, has been suggested as a potential target for therapeutic intervention. We designed a CD4 mutant (D1D2F43C) for site-specific coupling of compounds for screening against the cavity. Altogether, 81 cysteine-reactive compounds were designed, synthesized, and tested. Eight derivatives exceeded the affinity of native D1D2 for gp120. Structure-activity relationships (SAR) for derivatized CD4 binding to gp120 revealed significant plasticity of the Phe43 cavity and a narrow entrance. The primary contacts for compound recognition inside the cavity were found to be van der Waals interactions, whereas hydrophilic interactions were detected in the entrance. This first SAR on ligand binding to an interior cavity of gp120 may provide a starting point for structure-based assembly of small molecules targeting gp120-CD4 interaction.
Xie, Hui,Ng, Danny,Savinov, Sergey N.,Dey, Barna,Kwong, Peter D.,Wyatt, Richard,Smith III, Amos B.,Hendrickson, Wayne A.
p. 4898 - 4908
(2008/03/11)

Convenient palladium-catalyzed preparation of primary anilines using a fluorous benzophenone imine reagent
A novel fluoroalkyl benzophenone imine reagent (f-BPI) serves as a convenient ammonia surrogate for the palladium-catalyzed Buchwald-Hartwig amination of aryl halides. The highly fluorinated imine moiety acts as a handle for rapid purification of intermediates using fluorous chromatographic techniques, and is removed in a subsequent stage by acid hydrolysis to provide the corresponding primary anilines.
Cioffi, Christopher L.,Berlin, Michael L.,Herr, R. Jason
p. 841 - 845
(2007/10/03)

Design and SAR of thienopyrimidine and thienopyridine inhibitors of VEGFR-2 kinase activity
Novel classes of thienopyrimidines and thienopyridines have been identified as potent inhibitors of VEGFR-2 kinase. The synthesis and SAR of these compounds is presented, along with successful efforts to diminish EGFR activity present in the lead series.
Munchhof, Michael J.,Beebe, Jean S.,Casavant, Jeffery M.,Cooper, Beth A.,Doty, Jonathan L.,Higdon, R. Carla,Hillerman, Stephen M.,Soderstrom, Catherine I.,Knauth, Elisabeth A.,Marx, Matthew A.,Rossi, Ann Marie K.,Sobolov, Susan B.,Sun, Jianmin
p. 21 - 24
(2007/10/03)

Cross-coupling methods for the large-scale preparation of an imidazole - Thienopyridine: Synthesis of [2-(3-methyl-3H-imidazol-4-yl)-thieno[3,2-b]pyridin-7-yl] -(2-methyl-1H-indol-5-yl)-amine
The multihundred-gram synthesis of [2-(3-methyl-3H-imidazol-4-yl)-thieno[3,2-b]pyridin-7-yl] -(2-methyl-1H-indol-5-yl)-amine (1) is described utilizing a Stille cross-coupling of an iodothienopyridine (3) with 5-(tributylstannyl)-1-methylimidazole (11). Several cross-coupling methods were evaluated for the conversion of thienopyridine 3 to imidazole - thienopyridine 2, but only two were effective: the Stille coupling and a Negishi cross-coupling of the organozinc reagent derived from 2-(tertbutyldimethylsilyl)-1-methylimidazole and iodothienopyridine (3). The latter procedure worked well on laboratory scale (50 g), but was capricious upon scale-up. The issues with scale-up of an organostannane reagent are discussed, including control and analysis of organotin levels.
Ragan,Raggon,Hill,Jones,McDermott,Munchhof,Marx,Casavant,Cooper,Doty,Lu
p. 676 - 683
(2013/09/05)

Thienopyrimidine and thienopyridine derivatives useful as anticancer agents
The invention relates to compounds of the formulas 1 and 2 and to pharmaceutically acceptable salts and hydrates thereof, wherein X1, R1, R2and R11are as defined herein. The invention also relates to pharmaceutical compositions containing the compounds of formulas 1 and 2 and to methods of treating hyperproliferative disorders in a mammal by administering the compounds of formulas 1 and 2.
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(2008/06/13)

Synthesis and antibacterial activity of 4,7-dihydro-4-ethyl-7-oxothieno(3,2-b)pyridine-6-carboxylic acids
The synthesis of some new 4,7-dihydro-4-ethyl-7-oxothieno(3,2-b)pyridine-6-carboxylic acids with various substituents on position 2 is described. The evaluation of the anti-bacterial activity of some compounds shows an activity different to those of the thieno(2,3-b)pyridine series.
Malicorne,Bompart,Giral,Despaux
p. 3 - 11
(2007/10/02)

Process for preparing thiophene derivatives
A process for the preparation of 3-aminothiophenes or acid-addition salts thereof, which comprises reacting the corresponding 3-oxotetrahydrothiophenes with an acid-addition salt of hydroxylamine in the presence of a polar inert solvent and in the absence of a base at a temperature in the range of from 0° to 200° C.
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(2008/06/13)

(2-imidazolin-2-yl)thieno- and furo[2,3-b] and [3,2-b]pyridines and intermediates for the preparation thereof, and use of said compounds as herbicidal agents
There are provided novel (2-imidazolin-2-yl)-thieno and furo compounds, and intermediate compounds for the preparation thereof, and a method for controlling a wide variety of annual and perennial plant species therewith.
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(2008/06/13)

Dihydroimidazopyrrolopyridine, quinoline, thieno- and furo[2,3-b]pyridine, dihydrothieno- and furo[2,3-b]-pyridine, thieno- and furo[3,2-b]pyridine and dihydrothieno- and furo[3,2-b]pyridine herbicides and method for preparation thereof
This invention relates to novel herbicidally effective, dihydroimidazopyrrolopyridines and derivatives thereof which are useful for the control of undesirable monocotyledonous and dicotyledonous plant species. The invention also relates to a process for the preparation of said herbicidally effective compounds.
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(2008/06/13)

Imidazolidinones, and imidazolidinethiones, process and intermediates for the preparation thereof, and use of said compounds as herbicidal agents
This invention relates to novel imidazolidinone and imidazolidinethione compounds, a process and intermediates for the preparation of said compounds and a method for controlling undesirable plant species therewith.
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(2008/06/13)

Synthesis of Isomeric β-Haloethylthienopyrroles
The preparation of ethyl 4-(2-bromoethyl)thienopyrrole-5-carboxylate and ethyl 6-(2-bromoethyl)thienopyrrole-5-carboxylate by reaction of t-butyl 2-(2-thienyl)carbazate and t-butyl 2-(3-thienyl)carbazate with ethyl-5-bromo-2-oxopentanoate are described.
Galvez, C.,Garcia, F.
p. 393 - 395
(2007/10/02)

Nouvelle synthese et etude de la stabilite de l'amino-3 thiophene
A new synthesis of 3-aminothiophene is proposed starting from 3-thenoic acid via isopropyl 3-thienylcarbamate as intermediate.Thermal decomposition of this latter in alkaline medium gives 3-aminothiophene.NMR and mass spectral studies revealed that the instability of the amine is due to its polymerisation via thwe formation of the dimer di-3-thienylamine and the trimer tri-3-thienylamine.
Rault, S.,Cugnon de Sevricourt, M.,Robba, M.
p. 205 - 208
(2007/10/02)