- Preparation of an ABC tricyclic model of the cylindrospermopsin alkaloids via a biomimetically inspired pathway
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Two tricyclic guanidine model compounds 28 and 29 have been prepared in 12 steps from 1,5-pentanediol using a biomimetic synthetic approach. The pivotal reaction in the sequence is a tethered Biginelli condensation between 21/22 and β-keto esters 23 and 24. This journal is the Partner Organisations 2014.
- Evans, Daniel. M.,Horton, Peter N.,Hursthouse, Michael B.,Murphy, Patrick. J.
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- NEW ANALOGS AS ANDROGEN RECEPTOR AND GLUCOCORTICOID RECEPTOR MODULATORS
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The present invention relates to novel dihydropyridine derivatives of formula (I): as modulators of nuclear receptors selected from androgen receptor and glucocorticoid receptor, to processes for their preparation, to pharmaceutical compositions comprising said compounds and to the use of said for manufacturing a medicament for the treatment of pathological conditions or diseases that can improve by modulation of androgen receptor and/or glucocorticoid receptor, selected from cancer, metastasizing cancers, benign prostate hyperplasia, polycystic ovary syndrome (PCOS), hair loss, hirsutism, acne, hypogonadism, muscle wasting diseases, cachexia, Cushing's syndrome, anti-psychotic drug induced weight gain, obesity, post-traumatic stress disorder and alcoholism.
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Paragraph 0194; 0196; 0198
(2019/05/16)
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- Intermolecular acetoxyaminoalkylation of α-diazo amides with (diacetoxyiodo)benzene and amines
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Multicomponent reactions of diazo compounds have attracted much attention in recent years. Such transformations are generally conducted by applying transition metal catalysis and involve the corresponding metal carbenes as key intermediates. In this letter, a metal-free three-component intermolecular acetoxyaminoalkylation of α-diazo amides with tertiary aryl amines and (diacetoxyiodo)benzene is presented.
- D?ben, Nadine,Yan, Hong,Kischkewitz, Marvin,Mao, Jincheng,Studer, Armido
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supporting information
p. 7933 - 7936
(2019/01/04)
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- Addition of Diazo Compounds ipso -C-H Bond to Carbon Disulfide: Synthesis of 1,2,3-Thiadiazoles under Mild Conditions
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We describe here an operationally simple and straightforward synthesis method for a series of diverse 4,5-disubstituted 1,2,3-thiadiazoles via the nucleophilic addition of α-diazo carbonyl compounds to carbon disulfide. This method features using abundant and inexpensive carbon disulfide under mild reaction conditions.
- Zhang, Lei,Sun, Beiqi,Liu, Qianyi,Mo, Fanyang
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supporting information
p. 4275 - 4278
(2018/04/14)
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- Eco-friendly access to β-ketoamides: One-step catalyst-and solvent-free amidation of β-ketoesters under microwave irradiation
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A highly efficient and facile catalyst- and solvent-free one step amidation of β-ketoesters, without using any additional reagents, is described. Therefore, β-ketoamides are obtained in good to excellent yields by condensation of β-ketoesters with various primary or secondary amines. This eco-friendly protocol has been developed under microwave irradiation.
- Dechira, Khadidja,Taleb, Assya,Benmaati, Aouicha,Hacini, Salih,Zahmani, Hadjira Habib
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p. 152 - 160
(2018/03/21)
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- Direct Carboxylation of the Diazo Group ipso-C(sp2)-H bond with Carbon Dioxide: Access to Unsymmetrical Diazomalonates and Derivatives
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The direct carboxylation of the ipso-C(sp2)-H bond of a diazo compound with carbon dioxide under mild reaction conditions is described. This method is transition-metal-free, uses a weak base, and proceeds at ambient temperature under atmospheric pressure in carbon dioxide. The carboxylation exhibits high reactivity and is amenable to subsequent diversification. A series of unsymmetrical 1,3-diester/keto/amide diazo compounds are obtained with moderate to excellent yields (up to 99%) with good functional group compatibility.
- Liu, Qianyi,Li, Man,Xiong, Rui,Mo, Fanyang
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supporting information
p. 6756 - 6759
(2017/12/26)
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- O -Iodoxybenzoic Acid (IBX)-Iodine Mediated One-Pot Deacylative Sulfonylation of 1,3-Dicarbonyl Compounds: A Synthesis of β-Carbonyl Sulfones
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A combination of o-iodoxybenzoic acid (IBX) and a catalytic amount of iodine is found to promote a facile one-pot deacylative sulfonylation reaction of 1,3-dicarbonyl compounds with sodium sulfinates to yield β-carbonyl sulfones. The present method provides the target products bearing a wide variety of functional groups in one step and in good yields.
- Katrun, Praewpan,Songsichan, Teerawat,Soorukram, Darunee,Pohmakotr, Manat,Reutrakul, Vichai,Kuhakarn, Chutima
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supporting information
p. 1109 - 1121
(2017/02/24)
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- A convenient method for reduction dehalogenation of α-halocarbonyl compounds using benzenethiol in K+/CH3CN system
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Benzenethiol, as a reductive agent for the dehalogenation of various α-halocarbonyl compounds, is investigated in the K+/CH3CN system. The reaction affords the reduced compounds in high yields under mild reaction conditions, especially α-chlorocarbonyl compounds. Furthermore, the reaction performed under ultrasonic irradiation greatly shortens the reaction time.
- Dong, Wei-Li,Cai, Wen-Xi,Wu, Rui,Li, Zheng-Ming,Zhao, Wei-Guang,Liu, Xing-Hai
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p. 980 - 983
(2016/07/06)
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- Regiospecific synthesis of 1,4,5-trisubstituted 1,2,3-triazoles via enolate-azide cycloaddition between 1,3-dicarbonyl compounds and aryl azides
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A cycloaddition reaction at room temperature between aryl azides and 1,3-dicarbonyl compounds in the presence of potassium carbonate in dimethylsulphoxide yielded 10 4-ethoxycarbonyl-1-aryl-5-methyl-1H-1,2,3-triazoles and seven other closely-related compounds. The 1,2,3-triazoles, nine of which are new, were obtained in good to high yields and only the 1,4-regioisomers were formed.
- Nelson, Ronald,Kesternich, Víctor,Pérez-Fehrmann, Marcia,Jaldin, Sally,Marcourt, Laurence,Christen, Philippe
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p. 453 - 457
(2016/08/13)
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- Targeting dormant tuberculosis bacilli: Results for molecules with a novel pyrimidone scaffold
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Our inability to completely control TB has been due in part to the presence of dormant mycobacteria. This also renders drug regimens ineffective and is the prime cause of the appearance of drug-resistant strains. In continuation of our efforts to develop novel antitubercular agents that especially target dormant mycobacteria, a set of 55 new compounds belonging to the pyrimidone class were designed on the basis of CoMFA and CoMSIA studies, and these were synthesized and subsequently tested against both the dormant and virulent BCG strain of M. tuberculosis. Some novel compounds have been identified which selectively inhibit the dormant tuberculosis bacilli with significantly low IC50 values. This study reports the second molecule after TMC-207, having the ability to inhibit tuberculosis bacilli exclusively in its dormant phase. The synthesis was accomplished by a modified multicomponent Biginelli reaction. A classification model was generated using the binary QSAR approach - recursive partitioning (RP) to identify structural characteristics related to the activity. Physicochemical, structural, topological, connectivity indices, and E-state key descriptors were used for generation of the decision tree. The decision tree could provide insights into structure-activity relationships that will guide the design of more potent inhibitors. This paper reports the second molecule after TMC-207, with the ability to inhibit tuberculosis bacilli in its dormant phase. The paper reports molecules with a novel Pyrimidone Scaffold, the synthesis of which was accomplished with a modified multi-component Biginelli reaction. A classification model was generated using recursive partitioning (RP) technique to identify structural characteristics of the molecules with their varying activities.
- Joshi, Rohit R.,Barchha, Avinash,Khedkar, Vijay M.,Pissurlenkar, Raghuvir R. S.,Sarkar, Sampa,Sarkar, Dhiman,Joshi, Rohini R.,Joshi, Ramesh A.,Shah, Anamik K.,Coutinho, Evans C.
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p. 201 - 207
(2015/01/30)
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- Organocatalytic enantio- and diastereoselective conjugate addition to nitroolefins: When ketoamides surpass ketoesters
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Our findings on the bifunctional squaramide-catalyzed enantioselective conjugate addition of ketoamides to nitroolefins are disclosed. It appears that simple acyclic methylene ketoamides, unlike the extensively studied ketoesters, afford the products in excellent diastereoselectivities, and maintain high yields and enantioselectivities. Moreover, competition and kinetic studies were conducted to rationalize the observed reactivity and selectivity. The high level of diastereocontrol, along with the amenability of the amide group to postfunctionalization, dramatically increase the synthetic usefulness of the transformation.
- Du, Haiying,Rodriguez, Jean,Bugaut, Xavier,Constantieux, Thierry
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supporting information
p. 8458 - 8466
(2014/07/08)
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- Fe(III) Complex Compounds For The Treatment And Prophylaxis Of Iron Deficiency Symptoms And Iron Deficiency Anemias
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The invention relates to iron(III) complex compounds and pharmaceutical compositions comprising them for the use as medicaments, in particular for the treatment and/or prophylaxis of iron deficiency symptoms and iron deficiency anemias.
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Paragraph 0375; 0376; 0377; 0378; 0379; 0380
(2013/05/09)
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- Metal-free michael-addition-initiated three-component reaction for the regioselective synthesis of highly functionalized pyridines: Scope, mechanistic investigations and applications
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A metal-free and completely regioselective three-component synthesis of highly functionalized pyridines from 1,3-dicarbonyl derivatives and Michael acceptors has been achieved. Activated Michael acceptors, that is, β,γ-unsaturated α-oxo carbonyl derivatives, were utilized, allowing substitution at the 4-position and remarkable functional diversity at the 2-position of the pyridine ring. The scope and limitations of this environmentally friendly domino reaction are disclosed, with full experimental data, and the results of mechanistic investigations are discussed. The three-component synthesis of polysubstituted pyridines starting from 1,3-dicarbonyl compounds, α,β-unsaturated carbonyl derivatives and ammonium acetate has been studied, including the scope and mechanism. This methodology is a rare example of a totally regioselective multicomponent access to highly substituted pyridines that complies with many of the stringent criteria of sustainable chemistry. Copyright
- Allais, Christophe,Lieby-Muller, Frederic,Rodriguez, Jean,Constantieux, Thierry
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supporting information
p. 4131 - 4145
(2013/07/19)
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- Expedient synthesis of a 72-membered isoxazolino-β-ketoamide library by a 2·3-component reaction
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An efficient 2·3-component reaction (2·3CR; a 2-component reaction followed, in one pot, by a3-component reaction) is presented for the synthesis of isoxazolino-β-ketoamides. This 2·3CR proceeds by (i) a Meldrum's acid-generated acyl ketene, which is trapped by an amine to form a β-ketoamide intermediate in a 2CR followed, in one pot, by (ii) a Mannich reaction followed by elimination of dimethyl amine·HCl to generate an α,β-unsaturated β-ketoamide dipolarophile that reacts in a nitrile oxide 1,3-dipolar cycloaddition reaction. This one-pot 2·3CR process delivers the targeted isoxazolino-β-ketoamide product. A total of 72 compounds are presented, all of which have been submitted to the NIH Molecular Libraries Small Molecule Repository for high-throughput biological screening.
- Knapp, John M.,Zhu, Jie S.,Wood, Alex B.,Kurth, Mark J.
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scheme or table
p. 85 - 88
(2012/04/10)
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- Ru-catalyzed asymmetric hydrogenation of 3-oxoglutaric acid derivatives via solvent-assisted pinpoint recognition of carbonyls in close chemical propinquity
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Upon comparison of hydrogenation rates of various β-ketocarboxylic acid derivatives, β-ketoamides were found to be hydrogenated slightly faster than β-ketoesters in EtOH in the presence of [RuCl(benzene)(S)- SunPhos]Cl at 70 °C with 20 bar of hydrogen. In THF these differences were so sharpened that β-ketoamides were hydrogenated even faster than in EtOH while the esters were extremely slow. Based on these findings, a series of 3-oxoglutaric acid derived with ester and amide moieties on the two ends were hydrogenated to 3-hydroxyl products with high enantioselectivities.
- Li, Wanfang,Ma, Xin,Fan, Weizheng,Tao, Xiaoming,Li, Xiaoming,Xie, Xiaomin,Zhang, Zhaoguo
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supporting information; experimental part
p. 3876 - 3879
(2011/10/01)
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- Diversity-oriented synthesis of quinolines via Friedlaender annulation reaction under mild catalytic conditions
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An efficient and practical method has been manifested for the diversity-oriented synthesis of quinolines via Friedlaender annulation reaction for the generation of a wide range of structurally interesting and pharmacologically significant compounds by using eerie ammonium, nitrate as a catalyst (10 mol %) at ambient temperature in 45 min, A variety of functional groups are introduced at various positions of the quinoline moiety, and further the diversity of the core skeleton was expanded at R1 and R 2 positions by the synthesis of various hybrids. Initial screening of the compounds for cytotoxicity against a series of cancer cell lines showed promising results.
- Subhas Bose,Idrees, Mohd,Jakka,Venkateswara Rao
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scheme or table
p. 100 - 110
(2010/10/19)
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- Use of β,γ-unsaturated α-ketocarbonyls for a totally regioselective oxidative multicomponent synthesis of polyfunctionalized pyridines
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Versatile partners: α-Ketocarbonyls have been shown for the first time to be versatile partners in a Michael addition promoted oxidative domino threecomponent reaction under heterogeneous conditions. This multicomponent reaction sequence led to the development of a general synthesis of highly functionalized pyridines (see scheme), allowing selective and simultaneous incorporation of a substituent at the 4-position and a synthetically useful functionality at the strategic 2-position.
- Allais, Christophe,Constantieux, Thierry,Rodriguez, Jean
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supporting information; experimental part
p. 12945 - 12948
(2010/05/19)
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- Dihydropyrazolopyrimidine Inhibitors of KV1.5 (IKur)
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A series of dihydropyrazolopyrimidine inhibitors of KV1.5 (IKur) have been identified. The synthesis, structure-activity relationships and selectivity against several other ion channels are described.
- Vaccaro, Wayne,Huynh, Tram,Lloyd, John,Atwal, Karnail,Finlay, Heather J.,Levesque, Paul,Conder, Mary Lee,Jenkins-West, Tonya,Shi, Hong,Sun, Lucy
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experimental part
p. 6381 - 6385
(2009/09/06)
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- An efficient and rapid synthesis of β-carboxamide derivatives using 2,2-dimethyl-2H,4H-1,3-dioxin-4-ones by microwave irradiation
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A general, efficient and rapid method for the synthesis of various β-carboxamide derivatives using microwave irradiation is described. Excellent isolated yields were obtained in very short reaction times when conventional heating was replaced by microwave irradiation.
- Miriyala, Bruhaspathy,Williamson, John S.
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p. 7957 - 7959
(2007/10/03)
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- Angiotensin II antagonizers which are condensed pyridine derivatives
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The invention concerns pharmaceutically useful novel compounds of the formula I, in which R1, R2, R3, R4, R5, R6, R7, X and Z have the various meanings defined herein, and their non-toxic salts, and pharmaceutical compositions containing them. The novel compounds are of value in treating conditions such as hypertension and congestive heart failure. The invention further concerns processes for the manufacture of the novel compounds and the use of the compounds in medical treatment.
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- Ring Cleavage Reaction of 1,3-Oxazine-2,4(3H)-dione Derivatives with Amines
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The reactions of 3,6-dimethyl -1,3-oxazine-2,4(3H)-diones (1a, 1b, and 1c) with various amines were investigated under various conditions.Several reactions products were obtained such as the pyrimidines (3a, 3b, 3c, and 3d), the acetoacetamides (4a, 4b, and 4c), (4-chlorophenyl)urethane (5a), and ethyl acetoacetate (4d) with primary amines, and the acetoacetamides (4e and 4f), the urethanes (5a and 5b), the carboxamides (5c, 5d, 5e, and 5f), and the butenamides (7a, 7b, and 7c) with secondary amines.In the case of 1c with amine, alcohol used as a solvent reacted as a nucleophile to give the urethane (5a or 5b).
- Kinoshita, Toshio,Takeuchi, Kozue,Kondoh, Masaya,Furukawa, Sunao
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p. 2026 - 2029
(2007/10/02)
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- Preparation and pharmacologic activity of amido- derivatives of 3-methyl-3,4-dihydro benzo- and pyrido-1,2,4-triazin-3-acetic acids
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Thirteen amidoderivatives of 3-methyl-3,4-dihydro-6-R-benzo-1,2,4-triazin-3-yl-acetic acids and of 3-methyl-3,4-dihydro-pyrido [3,2-e]/[3,4-e]-1,2,4-triazin- 3-yl-acetic acids were prepared and submitted to a wide pharmacological screening. The dihydrobenzotriazine and dihydropyridotriazine moieties were endowed with a wide pharmacogenic capacity; in fact, several compounds exhibited high antiinflammatory [(I c), (I d), (II d), (V f), (VI f)], diuretic [(I f), (I g), (I h)] and antihypertensive activities [(I d), (III d)], as well as minor effects on the C.N.S.
- Boido,Novelli,Savelli,Sparatore,Russo,Filippelli,Susanna,Marmo
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p. 279 - 301
(2007/10/02)
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- A 4-Dimethylaminopyridine-Catalyzed Aminolysis of β-Ketoesters. Formation of β-Ketoamides
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Alkyl 3-oxoalkanoates (β-ketoesters) react with amines in the presence of a catalytic amount of 4-dimethylaminopyridine (DMAP) under mild conditions to form 3-oxoalkanamides (β-ketoamides) in good yields.
- Cossy, Janine,Thellend, Annie
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p. 753 - 755
(2007/10/02)
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- Reaction of Diketene-Acetone Adduct with Enamines, Ketene Acetals, Vinyl Ethers, and β-Diketones
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Diketene-acetone adduct (1) generates acetylketene (2) under heating.In order to compare the reactivity of 2 with that of diketene, the reaction of 1 with electron-rich olefins was investigated.On heating with 1 primary enamines (3a-d) produced the corresponding 3-substituted 2,6-dimethyl-4(1H)-pyridones (4a-d), while the tertiary enamine 3e gave the 4-pyrone derivative (7).The reaction of 1 with ketene acetals (8) gave the 2,2-diethoxy-2,3-dihydro-4-pyrone derivatives (9).The vinyl ether derivatives 13 similarly reacted with 1 to give the 4-pyrone derivative 15 or 16 as the major product.The result shows that both diketene and 2 react with electron-rich olefins in a similar manner.Keywords -- diketene; acetylketene; diketene-acetone adduct; enamine; ketene acetal; vinyl ether; 1,3-dioxin-4-one; 4-pyridone; 4-pyrone; cycloaddition
- Sato, Masayuki,Ogasawara, Hiromischi,Kato, Keiko,Sakai, Masako,Kato, Tetsuzo
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p. 4300 - 4305
(2007/10/02)
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- AMINES AND AMMONIUM COMPOUNDS. CLX. AMIDES OF ACETOACETIC ACID
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Some amides of acetoacetic acid were synthesized by reacting secondary amines with acetoacetic ester at 150 deg C.It was shown via PMR and mass spectrometry that the amount of the enol form is higher in the amides than in acetoacetic ester.
- Torosyan, G. O.,Gekchyan, G. G.,Panosyan, G. A.,Grigoryan, R. T.,Babayan, A. T.
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p. 1229 - 1231
(2007/10/02)
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- CONJUGATED SCHIFF'S BASES-14; CYCLOADDITION OF HETEROCUMULENES TO SOME 1-OXA-4-AZABUTADIENES
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1-Oxa-4-azabutadienes proved to be prone to react with some heterocumulenes after 1,3-cycloaddition patterns yielding various 5,5-disubstituted derivatives of 1,3-diaryl-hydanotoins as it was shown by the chemical and spectroscopic analysis.Relatively high yields, mild reaction conditions and a very weak effect of solvent polarity on the reaction rate suggested a synchroneous mechanism involving 1,2-migration of a substituent.
- Moskal, Janusz,Moskal, Alexandra,Milart, Piotr
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p. 1787 - 1792
(2007/10/02)
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