- A Bond-Weakening Borinate Catalyst that Improves the Scope of the Photoredox α-C-H Alkylation of Alcohols
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The development of catalyst-controlled, site-selective C(sp 3)-H functionalization reactions is currently a major challenge in organic synthesis. In this paper, a novel bond-weakening catalyst that recognizes the hydroxy group of alcohols through formation of a borate is described. An electron-deficient borinic acid-ethanolamine complex enhances the chemical yield of the α-C-H alkylation of alcohols when used in conjunction with a photoredox catalyst and a hydrogen atom transfer catalyst under irradiation with visible light. This ternary hybrid catalyst system can, for example, be applied to functional-group-enriched-peptides.
- Kanai, Motomu,Oisaki, Kounosuke,Sakai, Kentaro
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supporting information
p. 2171 - 2184
(2020/08/10)
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- Straightforward α-Amino Nitrile Synthesis Through Mo(CO)6-Catalyzed Reductive Functionalization of Carboxamides
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The selective reduction of amides into an intermediate hemiaminal catalyzed by Mo(CO)6 together with the inexpensive and easy to handle TMDS (1,1,3,3-tetramethyldisiloxane) as reducing agent, followed by subsequent trapping of the hemiaminal with a cyanide source, allows for the straightforward synthesis of α-amino nitriles. The methodology presented here, displays high levels of chemoselectivity allowing for the reduction of amides in the presence of functional groups such as ketones, imines, aldehydes, and acids, which affords a simple route for the synthesis of α-amino nitriles with a broad scope of functionalities in high yields. Furthermore, the applicability of this methodology is demonstrated by scale up experiments and by derivatization of the target compounds into synthetically interesting products. The selective cyanation is successfully applied in late stage functionalizations of amide containing drugs and prolinol derivatives.
- Trillo, Paz,Slagbrand, Tove,Adolfsson, Hans
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p. 12347 - 12351
(2018/09/10)
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- cGAS ANTAGONIST COMPOUNDS
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Disclosed are novel compounds of Formula (I) that are cGAS antagonists, methods of preparation of the compounds, pharmaceutical compositions comprising the compounds, and their use in medical therapy.
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Paragraph 0214; 0221
(2017/11/06)
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- Compounds IV
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The present application relates to new compounds of formula (I), to pharmaceutical compositions comprising the compounds, to processes for their preparation, and to the use of the compounds as leptin receptor modulator mimetics in the preparation of medic
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Page/Page column 8
(2009/08/18)
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- Highly chemoselective metal-free reduction of tertiary amides
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This communication describes the chemoselective metal-free reduction of tertiary amides to the corresponding amines. Hantzsch ester is used as a mild reducing agent for the reduction of trifluoromethanesulfonic anhydride activated amides providing the tertiary amines with high functional group tolerance. Copyright
- Barbe, Guillaume,Charette, Andre B.
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- 2-Amino-5-piperidinylimidazolone compounds and use thereof for beta-secretase modulation
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The present invention provides a 2-amino-5-piperidinylimidazolone compound of formula I The present invention also provides methods and compositions for the inhibition of β-secretase (BACE) and the treatment of β-amyloid deposits and neurofibrillary tangl
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Page/Page column 17
(2010/11/28)
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- Synthesis of diarylazepan-4-ones
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Synthesis of several 3,3-diarylazepan-4-ones and 5,5-diarylazepan-4-ones has been established starting from two tetrasubstituted olefins, which is derived from commercially available piperidine-3-carboxylic acid ethyl ester and piperidine-4-carboxylic aci
- Chang, Meng-Yang,Kung, Yung-Hua,Ma, Chih-Chong
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p. 199 - 202
(2007/10/03)
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- SILANOL DERIVATIVES AS INHIBITORS OF HISTONE DEACETYLASE
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The present invention is directed to certain silanol derivatives that are inhibitors of histone deacetylase and are therefore useful in the treatment of diseases associated with histone deacetylase activity. Pharmaceutical compositions and processes for p
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Page/Page column 96
(2008/06/13)
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- Pyrrolidine modulators of chemokine receptor activity
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The present invention is directed to pyrrolidine compounds of the formula I: (wherein R1, R2, R3, R4, R5, R6, R14and n are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-5 and/or CCR-3.
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- Biohydroxylation reactions catalyzed by enzymes and whole-cell systems
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The biohydroxylation of a number of cyclic substrates (3-24) containing aromatic side chains was used to compare substrate specificity and selectivity of hydroxylation using microbial enzymes and whole-cell biocatalysts. In general, the regioselectivity of reaction was remarkably similar between the different catalysts in that little aromatic or benzylic, but significant aliphatic hydroxylation was observed. However, a more detailed investigation of isolated products showed complementary substrate specificity, functional group compatibility, and regioselectivity of hydroxylation. Substrate specificity and regioselectivity could be further modulated by small changes to the nature of the aromatic side chain, which appears to play an important role in substrate recognition.
- Flitsch, Sabine L.,Aitken, Suzanne J.,Chow, Cathy S.-Y.,Grogan, Gideon,Staines, Adam
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- Novel piperidine σ receptor ligands as potential antipsychotic drugs
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σ receptor ligands represent a new class of potential antipsychotic drugs. This paper presents the structure-activity relationships leading to novel disubstituted piperidine σ ligands, which have little or no affinity for dopamine D2 receptors. Selectivity for σ sites over dopamine D2 or serotonin 5-HT2 receptors appears to be governed by the chemical nature of the piperidine nitrogen substituent, its distance from the basic nitrogen, and its orientation relative to the other piperidine substituent. Several of these compounds have good oral potency in some animal models used to evaluate potential antipsychotic drugs. The N-cyclopropylmethyl ketones and ethers (e.g. 6i (DuP 734), 6q, 18a, and 18n) have the best in vivo potency. Compounds 6i (DuP 734) and 6q did not cause catalepsy in the rat, even at very high doses. On the basis of the pharmacology profiles of these σ ligands, we propose these compounds may be effective antipsychotic drugs, which do not induce extrapyramidal side effects or tardive dyskinesia.
- Gilligan,Cain,Christos,Cook,Drummond,Johnson,Kergaye,McElroy,Rohrbach,Schmidt,Tam
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p. 4344 - 4361
(2007/10/02)
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- Piperidine ether derivatives as psychotropic drugs or plant fungicides
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There are provided piperidine ether derivatives, pharmaceutical and agricultural compositions containing them useful for treating physiological or drug induced psychosis or dyskinesia in a mammal or fungal disease in plants. Also provided are methods for preparing these compounds.
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- 4-Phenoxymethyl-piperidines
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4-Phenoxymethyl-piperidines of the formula STR1 wherein R is hydrogen, halogen, nitro, lower alkyl or lower alkoxy, in the form of the free base or an acid addition salt, are provided and they are useful as intermediates in the production of anti-hypertensive agents through condensation with (a) propyl chloride and then with an adenine, or (b) a propyl indole.
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