- Rapid microwave promoted Sonogashira coupling reactions on solid phase
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A microwave-enhanced, rapid, and efficient solid-phase version of the Sonogashira reaction is presented. It has been applied to the coupling of aryl iodides and bromides with various acetylene derivatives giving excellent yields in 15-25 min. The scopes of homogeneous, solventless, and solid-phase conditions for Sonogashira coupling of aryl halides are compared.
- Erdelyi, Mate,Gogoll, Adolf
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Read Online
- Tetraalkylammonium dichloroiodates as iodinating agents: Absence of activity in solid phases and superelectrophilic activity in sulfuric acid
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In contrast to published results, tetraalkylammonium dichloroiodates (Alk4N+ICl2-) cannot be iodinating reagents for arenes in solvent-free conditions. Nevertheless, tetraalkylammonium dichloroiodates in sulfuric acid solutions or in the presence of Ag 2SO4 in H2SO4 possess superelectrophilic properties and act as very convenient and efficient iodinating agents for deactivated arenes. Georg Thieme Verlag Stuttgart.
- Filimonov, Victor D.,Semenischeva, Nadya I.,Krasnokutskaya, Elena A.,Ho, Yun Hwang,Chi, Ki-Whan
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Read Online
- Transition metal-free synthesis of primary amides from aldehydes and hydroxylamine hydrochloride
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Primary aromatic amides can be synthesized from aldehydes and hydroxylamine hydrochloride in the presence of Cs2CO3. Various aromatic aldehydes (include some heteroaromatic aldehydes) are able to generate the corresponding aromatic amides in moderate to excellent yields.
- Wang, Wei,Zhao, Xue-Mei,Wang, Jing-Li,Geng, Xin,Gong, Jun-Fang,Hao, Xin-Qi,Song, Mao-Ping
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Read Online
- Efficient nitriding reagent and application thereof
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The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.
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Paragraph 0514-0516
(2021/03/31)
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- Visible light-mediated synthesis of amides from carboxylic acids and amine-boranes
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Here, a photocatalytic deoxygenative amidation protocol using readily available amine-boranes and carboxylic acids is described. This approach features mild conditions, moderate-to-good yields, easy scale-up, and up to 62 examples of functionalized amides with diverse substituents. The synthetic robustness of this method was also demonstrated by its application in the late-stage functionalization of several pharmaceutical molecules.
- Chen, Xuenian,Kang, Jia-Xin,Ma, Yan-Na,Miao, Yu-Qi
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supporting information
p. 3595 - 3599
(2021/06/06)
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- Nitromethane as a nitrogen donor in Schmidt-type formation of amides and nitriles
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The Schmidt reaction has been an efficient and widely used synthetic approach to amides and nitriles since its discovery in 1923. However, its application often entails the use of volatile, potentially explosive, and highly toxic azide reagents. Here, we report a sequence whereby triflic anhydride and formic and acetic acids activate the bulk chemical nitromethane to serve as a nitrogen donor in place of azides in Schmidt-like reactions. This protocol further expands the substrate scope to alkynes and simple alkyl benzenes for the preparation of amides and nitriles.
- Jiao, Ning,Liu, Jianzhong,Qiu, Xu,Song, Song,Wei, Jialiang,Wen, Xiaojin,Zhang, Cheng,Zhang, Ziyao
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supporting information
p. 281 - 285
(2020/01/28)
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- Transamidation for the Synthesis of Primary Amides at Room Temperature
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Various primary amides have been synthesized using the transamidation of various tertiary amides under metal-free and mild reaction conditions. When (NH4)2CO3 reacts with a tertiary amide bearing an N-electron-withdrawing substituent, such as sulfonyl and diacyl, in DMSO at 25 °C, the desired primary amide product is formed in good yield with good funcctional group tolerance. In addition, N-tosylated lactam derivatives afforded their corresponding N-tosylamido alkyl amide products via a ring opening reaction.
- Chen, Jiajia,Lee, Sunwoo,Xia, Yuanzhi
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supporting information
(2020/05/05)
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- Base promoted peroxide systems for the efficient synthesis of nitroarenes and benzamides
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A useful and efficient approach for the synthesis of nitroarenes from several aromatic amines (including heterocycles) using peroxide and base has been developed. This oxidative reaction is very easy to handle and afforded the products in good yields. Formation of benzamides from benzylamine was also successfully carried out with this metal-free catalytic system in good to excellent yields.
- Gupta, Sampa,Ansari, Alisha,Sashidhara, Koneni V.
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supporting information
(2019/09/07)
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- Chemoselective Synthesis of Aryl Ketones from Amides and Grignard Reagents via C(O)-N Bond Cleavage under Catalyst-Free Conditions
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Conversion of a wide range of N-Boc amides to aryl ketones was achieved with Grignard reagents via chemoselective C(O)-N bond cleavage. The reactions proceeded under catalyst-free conditions with different aryl, alkyl, and alkynyl Grignard reagents. α-Ketoamide was successfully converted to aryl diketones, while α,β-unsaturated amide underwent 1,4-addition followed by C(O)-N bond cleavage to provide diaryl propiophenones. N-Boc amides displayed higher reactivity than Weinreb amides with Grignard reagents. A broad substrate scope, excellent yields, and quick conversion are important features of this methodology.
- Sureshbabu, Popuri,Azeez, Sadaf,Muniyappan, Nalluchamy,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
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p. 11823 - 11838
(2019/10/02)
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- Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and N-Halosuccinimide
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A one-pot universal approach for transforming arylamines to aryl halides via reaction with sodium nitrite (NaNO2) and N-halosuccinimide (NXS) in DMF at room temperature under metal- and acid-free condition is described. This new protocol that is complementary to the Sandmeyer reaction, is suggested to involve the in situ generation of nitryl halide induce nitrosylation of aryl amine to form the diazo intermediate which is halogenated to furnish the aryl halide.
- Mukhopadhyay, Sushobhan,Batra, Sanjay
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supporting information
p. 14622 - 14626
(2018/09/21)
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- Site-selective C-H/C-N activation by cooperative catalysis: Primary amides as arylating reagents in directed C-H arylation
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Direct C-H arylation of nonacidic C(sp)-H bonds with primary amides as arylating reagents via highly chemoselective C-H/C-N/C-C cleavages has been accomplished for the first time. The key to the success is the cooperative combination of rhodium(I) catalys
- Meng, Guangrong,Szostak, Michal
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p. 7251 - 7256
(2017/11/09)
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- FAK AND FLT3 INHIBITORS
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The use of a compound of the formula (I): (Formula (I)) in the preparation of a medicament for treating Acute Myeloid Leukemia or a disease ameliorated by the inhibition of Flt3, or Flt3 and FAK.
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Page/Page column 157-158
(2014/03/22)
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- FAK INHIBITORS
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A compound of the formula (I): where R1 or R2 is a cycle amine group and R5 is an aromatic group with a carbonyl containing substituent for use as a FAK inhibitor.
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Page/Page column 155; 156
(2012/09/10)
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- Superelectrophilic iodination of deactivated arenes with triiodoisocyanuric acid
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The reaction of triiodoisocyanuric acid (TICA) with deactivated arenes in acidic medium led to the efficient and regioselective formation of the corresponding iodoarenes, in 55-88% isolated yield. The acidity of the medium was found to be the most important factor influencing the electrophilic iodination of weakly nucleophilic substrates by TICA. Georg Thieme Verlag Stuttgart New York.
- Da Ribeiro, Rodrigo S.,Esteves, Pierre M.,De Mattos, Marcio C. S.
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experimental part
p. 739 - 744
(2011/04/24)
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- Oxidative iodination of deactivated arenes in concentrated sulfuric acid with I2/NaIO4 and KI/NaIO4 iodinating systems
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Deactivated arenes were mono- or diiodinated with strong electrophilic I+ reagents, which were prepared from NaIO4 and either I2 or KI in concentrated H2SO4 (minimum 95% by weight). In general a small excess of the dark brown iodinating solution was used (1.1/1.5 equivalents, for nitrobenzene two equivalents was required). The iodinations were conducted at 25-30 °C with a reaction time of 1-2 hours using either a 'direct' or an 'inverse' method of aromatic iodination to give mono- or diiodinated pure products in 31-91% optimized yields. Georg Thieme Verlag Stuttgart.
- Kraszkiewicz, Lukasz,Sosnowski, Maciej,Skulski, Lech
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p. 1195 - 1199
(2007/10/03)
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- PHENYLTHIOACETIC ACID DERIVATIVES AND USE THEREOF
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The invention relates to novel phenylthioacetic acid derivatives of formula (I), to a method for the production thereof, to the use thereof for the treatment and/or prophylaxis of diseases, in addition to the use thereof in the production of medicaments for the treatment and/or prophylaxis of diseases, in particular for the treatment and/or prevention of cardiovascular diseases, in particular dyslipidaemia and arteriosclerosis. The compounds act as modulators for the PRAR-alpha receptor.
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Page/Page column 64
(2010/02/14)
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- A Novel Aromatic Iodination Method, with Sodium Periodate Used as the Only Iodinating Reagent
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Benzene, halobenzenes and some deactivated arenes readily reacted in anhydrous NaIO4/AcOH/Ac2O/concd. H2SO4 mixtures to afford, after quenching with excess aqueous Na2SO3 solution (a reducing agent), purified iodinated products in 27-88 percent yields. This novel method of aromatic iodination is simple, fairly effective and environmentally safe.
- Lulinski, Piotr,Sosnowski, Maciej,Skulski, Lech
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p. 671 - 675
(2007/10/03)
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- Easy, inexpensive and effective oxidative iodination of deactivated arenes in sulfuric acid
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Two 'model' deactivated arenes, benzoic acid and nitrobenzene, were effectively monoiodinated within 1 h at 25-30 °C, with strongly electrophilic I+ reagents, prior prepared from diiodine and various oxidants (CrO3, KMnO4, active MnO2, HIO 3, NaIO3, or NaIO4) in 90% (v/v) concd sulfuric acid (ca. 75 mol% H2SO4). Next, an I2/ NaIO3/90% (v/v) concd H2SO4 exemplary system was used to effectively mono- or diiodinate a number of deactivated arenes. All former papers dealing with the direct iodination of deactivated arenes are briefly reviewed.
- Kraszkiewicz, Lukasz,Sosnowski, MacIej,Skulski, Lech
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p. 9113 - 9119
(2007/10/03)
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- Chemical Manganese Dioxide (CMD): Its application to the oxidative iodination of benzene, halobenzenes and some deactivated arenes
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After comparing our previous and newer results for numerous oxidative aromatic iodination experiments using various brands (of active MnO2 as the oxidants, we recommend the use of a Chemical Manganese Dioxide (Aldrich CMD; 90+% (MnO2) as the oxidant of choice, since it is satisfactorily pure and chemically active, and is notably less costly than other options.
- Lulinski, Piotr,Krassowska-Swiebocka, Barbara,Skulski, Lech
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p. 595 - 601
(2007/10/03)
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- Synthesis of a high-affinity Fluorescent PPARγ ligand for high-throughput fluorescence polarization assays
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Members of the peroxisome proliferator activated receptor (PPAR) family of transcription factors are under investigation as molecular targets for the treatment of numerous diseases including Alzheimer's, asthma, atherosclerosis, inflammation, multiple sclerosis, cancer, and diabetes. We employed the X-ray crystal structure of the PPARγ subtype complexed with the potent small molecule agonist GI262570 (farglitazar) to design and synthesize a novel fluorescent and high-affinity probe for homogeneous and high-throughput fluorescent polarization (FP) assays. Examination of this X-ray structure revealed that the phenyl carbon atom meta to the oxazole moiety of GI262570 is exposed to solvent at the bottom of a narrow protein cavity. A derivative of GI262570 was synthesized bearing a linear phenylacetylene-derived side chain comprising propargylamine coupled to fluorescein. This fluorescent analogue was designed to project the fluorophore into the adjacent protein cavity with minimal effects on receptor affinity and maximal effects on fluorescence polarization properties. The recombinant PPARγ ligand binding domain protein bound tightly and specifically to this probe with K d=61±14 nM as determined by FP measurements. Competition binding assays with known PPARγ ligands provided Ki values that were highly correlated with analogous values obtained by scintillation proximity (SP) assays. This fluorescent PPARγ probe enables high-throughput and homogenous FP assays for the identification of novel endogenous and exogenous PPARγ ligands, and this rational ligand design approach may be applied to other therapeutically important members of the nuclear hormone receptor superfamily.
- DeGrazia, Michael J.,Thompson, Jerry,Vanden Heuvel, John P.,Peterson, Blake R.
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p. 4325 - 4332
(2007/10/03)
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- Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists
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The present invention provides compounds and pharmaceutical compositions that act as antagonists at metabotropic glutamate receptors, and that are useful for treating neurological diseases and disorders. Methods of preparing the compounds also are disclosed.
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- Substituted benzamide inhibitors of rhinovirus 3C protease
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Nonpeptide benzamide-containing inhibitors of human rhinovirus (HRV) 3C protease are described.
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Page column 10
(2010/01/31)
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- Diaminopropionic acid derivatives
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A compound of formula 1a which is useful for treating reperfusion injury, and salts, prodrugs, and related compounds.
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- Substituted benzamide inhibitors of human rhinovirus 3C protease: Structure-based design, synthesis, and biological evaluation
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A series of nonpeptide benzamide-containing inhibitors of human rhinovirus (HRV) 3C protease was identified using structure-based design. The design, synthesis, and biological evaluation of these inhibitors are reported. A Michael acceptor was combined with a benzamide core mimicking the P1 recognition element of the natural 3CP substrate, α,β-Unsaturated cinnamate esters irreversibly inhibited the 3CP and displayed antiviral activity (EC50 0.60/μM, HRV-16 infected H1-HeLa cells). On the basis of cocrystal structure information, a library of substituted benzamide derivatives was prepared using parallel synthesis on solid support. A 1.9 A? cocrystal structure of a benzamide inhibitor in complex with the 3CP revealed a binding mode similar to that initially modeled wherein covalent attachment of the nucleophilic cysteine residue is observed. Unsaturated ketones displayed potent reversible inhibition but were inactive in the cellular antiviral assay and were found to react with nucleophilic thiols such as DTT.
- Reich, Siegfried H.,Johnson, Theodore,Wallace, Michael B.,Kephart, Susan E.,Fuhrman, Shella A.,Worland, Stephen T.,Matthews, David A.,Hendrickson, Thomas F.,Chan, Fora,Meador III, James,Ferre, Rose Ann,Brown, Edward L.,DeLisle, Dorothy M.,Patick, Amy K.,Binford, Susan L.,Ford, Clifford E.
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p. 1670 - 1683
(2007/10/03)
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- Oxidative iodination of arenes with manganese(IV) oxide or potassium permanganate as the oxidants
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Novel and easy laboratory methods (novel Procedures 1-4) are presented for the oxidative mono- and diiodination of both activated and deactivated arenes, which gave the pure iodinated products in 62-89% yields. The reactions were carried out in the anhydrous, strongly acidic system, I2/activated MnO2/AcOH/Ac2O/concd H2SO4, firstly at r.t. for 2 h, then at 45-55 °C for 2-9 h. The resulting mixtures were poured into excess aq Na2SO3 solution buffered with (NH4)2CO3 to neutralize H2SO4. The following workups are given. Similarly, on carrying out the iodination reactions (at 35 °C, for one hour) in the anhydrous, strongly acidic system, I2/KMnO4/AcOH/Ac2O/concd H2SO4, it was possible to mono- or diiodinate several deactivated arenes in 73-87% yields (improved Procedures 5 and 6).
- Lulinski, Piotr,Skulski, Lech
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p. 115 - 120
(2007/10/03)
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- The direct iodination of arenes with chromium(VI) oxide as the oxidant
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An easy and cheap laboratory method is presented for the direct mono- and diiodination of a number of activated and deactivated arenes. The main iodination reactions occurred at the temperatures not exceeding 65°C for 0.5-12 h in the anhydrous, strongly acidic liquid system, I2/AcOH/Ac2O/H2SO4, in the presence of prior dissolved CrO3 used as the oxidant. The yields of the pure iodinated products varied from 31% (for 3,5- diiodobenzoic acid) up to 90% (for 4-iodoanisole). So far, benzonitrile and some oxidizable aromatics, e.g. naphthalene, fluorene, xanthene, and thiophene, have been found to be unsuitable for the effective iodination. Nevertheless, this novel, simple method of direct iodination is worthy to be extended to other appropriate aromatics.
- Lulinski, Piotr,Skulski, Lech
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p. 1665 - 1669
(2007/10/03)
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