- Efficiency Enhancement of a Photocatalytic Decarbonylation of an Aminocyclopropenone by Benzothiophene Substitution
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To improve the efficiency of the photocatalytic decarbonylation of cyclopropenones, the effects of substituents on cyclopropenone were explored. A benzothiophene-substituted aminocyclopropenone exhibited significantly improved decarbonylation efficiency t
- Mishiro, Kenji,Nomura, Mitsuki,Furuyama, Taniyuki,Kunishima, Munetaka
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p. 3625 - 3636
(2021/03/03)
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- Phototriggered Active Alkyne Generation from Cyclopropenones with Visible Light-Responsive Photocatalysts
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A photocatalytic active alkyne generation reaction was developed using cyclopropenone as a starting reagent. Visible light-responsive photocatalysts induced cyclopropenone decarbonylation. The resulting highly reactive alkyne could be used directly, witho
- Mishiro, Kenji,Kimura, Takeshi,Furuyama, Taniyuki,Kunishima, Munetaka
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supporting information
p. 4101 - 4105
(2019/06/17)
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- Biocatalytic N-Acylation of Amines in Water Using an Acyltransferase from Mycobacterium smegmatis
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A straightforward one-step biocatalyzed synthesis of different N-acyl amides in water was accomplished using the versatile and chemoselective acyltransferase from Mycobacterium smegmatis (MsAcT). Acetylation of primary arylalkyl amines was achieved with a range of acetyl donors in biphasic systems within 1 hour and at room temperature. Vinyl acetate was the best donor which could be employed in the N-acetylation of a large range of primary amines in excellent yields (85–99%) after just 20 minutes. Other acyl donors (including formyl-, propionyl-, and butyryl-donors) were also efficiently employed in the biocatalytic N-acylation. Finally, the biocatalyst was tested in transamidation reactions using acetamide as acetyl donor in aqueous medium, reaching yields of 60–70%. This work expands the toolbox of preparative methods for the formation of N-acyl amides, describing a biocatalytic approach easy to accomplish under mild conditions in water. (Figure presented.).
- Contente, Martina Letizia,Pinto, Andrea,Molinari, Francesco,Paradisi, Francesca
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p. 4814 - 4819
(2018/11/10)
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- PYRAZOLOPYRIMIDINE DERIVATIVES, PREPARATION METHOD THEREOF, AND PHARMACEUTICAL COMPOSITION FOR USE IN PREVENTING OR TREATING CANCER, AUTOIMMUNE DISEASE AND BRAIN DISEASE CONTAINING THE SAME AS AN ACTIVE INGREDIENT
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The present invention relates to a pyrazolopyrimidine derivative, a preparation method thereof and a pharmaceutical composition comprising the same as an active ingredient for the prevention or treatment of cancer, autoimmune disease and brain disease. The pyrazolopyrimidine derivative of the present invention exhibits excellent Bruton's tyrosine kinase inhibition activity, so that it can be effectively used as a pharmaceutical composition for the prevention or treatment of cancer, autoimmune disease and Parkinson's disease.
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Paragraph 342-346
(2018/12/02)
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- Identification of an Imine Reductase for Asymmetric Reduction of Bulky Dihydroisoquinolines
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A new imine reductase from Stackebrandtia nassauensis (SnIR) was identified, which displayed over 25- to 1400-fold greater catalytic efficiency for 1-methyl-3,4-dihydroisoquinoline (1-Me DHIQ) compared to other imine reductases reported. Subsequently, an efficient SnIR-catalyzed process was developed by simply optimizing the amount of cosolvent, and up to 15 g L-1 1-Me DHIQ was converted completely without a feeding strategy. Furthermore, the reaction proceeded well for a panel of dihydroisoquinolines, affording the corresponding tetrahydroisoquinolines (mostly in S-configuration) in good yields (up to 81%) and with moderate to excellent enantioselectivities (up to 99% ee).
- Li, Hao,Tian, Ping,Xu, Jian-He,Zheng, Gao-Wei
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supporting information
p. 3151 - 3154
(2017/06/23)
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- Phototriggered Dehydration Condensation Using an Aminocyclopropenone
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A phototriggered dehydration condensation using an aminocyclopropenone has been developed. The UV irradiation of an aminocyclopropenone generated a highly reactive ynamine in situ and the dehydration condensation of a carboxylic acid and an amine coexisting in the reaction solution smoothly proceeded to afford an amide. This reaction is completely controllable by the ON/OFF states of a UV lamp.
- Mishiro, Kenji,Yushima, Yuki,Kunishima, Munetaka
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supporting information
p. 4912 - 4915
(2017/09/23)
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- A Titanium(III)-Catalyzed Reductive Umpolung Reaction for the Synthesis of 1,1-Disubstituted Tetrahydroisoquinolines
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A catalytic reductive C1-acylation of 3,4-dihydroisoquinolines is presented that gives direct access to 1,1-disubstituted tetrahydroisoquinolines. The reaction is a titanium(III)-catalyzed reductive umpolung process in which nitriles act as effective acylation agents. The method is highly chemo- and regioselective and is demonstrated in 20 examples. It is well-suited for the large-scale synthesis of functionalized tetrahydroisoquinoline products, which is exemplified in the form of a six-step synthesis of (±)-3-demethoxyerythratidinone. (Figure Presented).
- Luu, Hieu-Trinh,Wiesler, Stefan,Frey, Georg,Streuff, Jan
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supporting information
p. 2478 - 2481
(2015/05/27)
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- Microwave-assisted heteropolyanion-based ionic liquids catalyzed transamidation of non-activated carboxamides with amines under solvent-free conditions
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An environmentally benign and highly efficient protocol for the transamidation of non-activated carboxamides with amines using heteropolyanion-based ionic liquids as catalysts under microwave-assisted and solvent-free conditions has been developed. As evaluated by the reactions of a structurally diverse set of amides and amines, the scope and utility of the transamidation proved to be quite general. Operational simplicity, solvent-free media, the potential reusability of catalysts and wide functional group tolerance are attractive features. This method provides a much improved protocol over the existing methods.
- Fu, Renzhong,Yang, Yang,Chen, Zhikai,Lai, Wenchen,Ma, Yongfeng,Wang, Quan,Yuan, Rongxin
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p. 9492 - 9499
(2015/03/04)
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- Amidation of aldehydes and alcohols through α-iminonitriles and a sequential oxidative three-component strecker reaction/thio-michael addition/alumina-promoted hydrolysis process to access β-mercaptoamides from aldehydes, amines, and thiols
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Mild and general alumina-promoted hydrolysis conditions for converting α-iminonitriles into carboxamides have been developed. In combination with the oxidative three-component Strecker reaction, the one-pot direct amidation of aldehydes and alcohols is reported. Subsequently, an Yb(OTf) 3-catalyzed Michael addition of thiols to α,β-unsaturated α-iminonitriles is reported for the synthesis of β-mercapto-α- iminonitriles. The successful integration of an oxidative Strecker reaction, thio-Michael addition, and neutral-alumina-promoted hydrolysis of β-mercapto-α-iminonitriles into a three-component one-pot process allowed us to develop the direct conversion of amines, aldehydes, and thiols into β-mercaptoamides. All of these procedures were applicable to aromatic and aliphatic amines and aldehydes. First direct: The direct amidation reactions of aldehydes and alcohols were performed in combination with the oxidative three-component synthesis of α-iminonitriles. In addition, β-mercaptoamides were readily accessed from α,β-unsaturated aldehydes, amines, and thiols by a sequential process that involved a three-component Strecker reaction, Yb(OTf)3-catalyzed thio-Michael addition, and hydrolysis of the resulting β-mercapto-α-iminonitriles (see scheme). Copyright
- Gualtierotti, Jean-Baptiste,Schumacher, Xavier,Fontaine, Patrice,Masson, Géraldine,Wang, Qian,Zhu, Jieping
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supporting information
p. 14812 - 14819
(2013/01/15)
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- Inhibition of the production of the Pseudomonas aeruginosa virulence factor pyocyanin in wild-type cells by quorum sensing autoinducer-mimics
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Pseudomonas aeruginosa is a notorious human pathogen associated with a range of life-threatening nosocomial infections. There is an increasing problem of antibiotic resistance in P. aeruginosa, highlighted by the emergence of multi-drug resistant strains.
- Morkunas, Bernardas,Galloway, Warren R. J. D.,Wright, Megan,Ibbeson, Brett M.,Hodgkinson, James T.,O'Connell, Kieron M. G.,Bartolucci, Noemi,Valle, Martina Della,Welch, Martin,Spring, David R.
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p. 8452 - 8464
(2013/01/15)
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- Synthesis and pharmacological evaluation of 1-isopropyl-1,2,3,4- tetrahydroisoquinoline derivatives as novel antihypertensive agents
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A series of 1-isopropyl-1,2,3,4-tetrahydroisoquinoline derivatives were synthesized and their bradycardic activities were evaluated in isolated guinea pig right atria. Structure-activity relationship studies revealed that the introduction of an appropriate substituent and its position on the 1,2,3,4-tetrahydroisoquinoline ring are essential for potent in vitro activity. Furthermore, the tether between the piperidyl moiety and the terminal aromatic ring is important for potent antihypertensive activity. Oral administration of 6-fluoro-1-isopropyl-2-{[1-(2-phenylethyl)piperidin-4-yl]carbonyl}-1,2,3, 4-tetrahydroisoquinoline (3b) to spontaneously hypertensive rats (SHR) elicited antihypertensive effects without inducing reflex tachycardia, which is often caused by traditional L-type Ca2+ channel blockers.
- Watanuki, Susumu,Matsuura, Keisuke,Tomura, Yuichi,Okada, Minoru,Okazaki, Toshio,Ohta, Mitsuaki,Tsukamoto, Shin-Ichi
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scheme or table
p. 1029 - 1037
(2011/10/18)
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- A highly efficient and enantioselective access to tetrahydroisoquinoline alkaloids: Asymmetric hydrogenation with an iridium catalyst
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Efficient and enantioselective: Using the iodine-bridged dimeric iridium complex [{Ir(H)[(S,S)-(f)-binaphane]}2(μ-I)3] +I- (1) a wide range of tetrahydroisoquinoline alkaloids, including the substructure of the pharmaceutical drug solifenacin, were obtained with excellent enantioselectivities and high turnover numbers (see scheme). Copyright
- Chang, Mingxin,Li, Wei,Zhang, Xumu
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supporting information; experimental part
p. 10679 - 10681
(2011/12/05)
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- Tetrabenzylpyrophosphate: An efficient catalyst for the synthesis of carboxamides from carboxylic acids and amines
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An efficient method for the synthesis of simple and sterically hindered carboxamides from various carboxylic acids and amines using tetrabenzylpyrophosphate (TBPP) as a coupling agent in the presence of 4-(dimethylamino)pyridine (DMAP) is described. The r
- Thirupathi Reddy,Narsimha Reddy,Raghotham Reddy,Crooks, Peter A.
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p. 528 - 529
(2008/09/21)
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- Enantioselective synthesis of 2-substituted 2-phenylethylamines by lithiation - Substitution sequences: Synthetic development and mechanistic pathway
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The lithiation and asymmetric substitution of N-(2-phenylethyl)isobutyramide (2) with selected electrophiles, under the influence of (-)-sparteine, provides benzylically substituted products in 58-90% yields with enantiomeric ratios (ers) from 72:28 to 91:9. Syntheses of enantioenriched dihydroisoquinolines (S)-18 and (S)-19 and a tetrahydroisoquinoline (4S)-20 provide examples of synthetic applications. Mechanistic investigations suggest the enantiodetermining step at -78°C is a dynamic thermodynamic resolution.
- Laumer, Jason M.,Kim, Dwight D.,Beak, Peter
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p. 6797 - 6804
(2007/10/03)
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- An activated phosphate for an efficient amide and peptide coupling reagent
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An activated phosphate for an efficient amide and peptide coupling reagent was discussed. Activation of diethyl phosphates was realized by attaching trifluoromethanesulfonanilide as an efficient leaving group and the phosphate proved to be a promising amide and peptide coupling reagent. Results showed that reactions of a primary amine with α-branched carboxylic acids and benzoic acid gave within 1 h the amides in quite high yield.
- Yasuhara, Tomohisa,Nagaoka, Yasuo,Tomioka, Kiyoshi
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p. 2901 - 2902
(2007/10/03)
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