- Interrupted Pyridine Hydrogenation: Asymmetric Synthesis of δ-Lactams
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Metal-catalyzed hydrogenation is an effective method to transform readily available arenes into saturated motifs, however, current hydrogenation strategies are limited to the formation of C?H and N?H bonds. The stepwise addition of hydrogen yields reactive unsaturated intermediates that are rapidly reduced. In contrast, the interruption of complete hydrogenation by further functionalization of unsaturated intermediates offers great potential for increasing chemical complexity in a single reaction step. Overcoming the tenet of full reduction in arene hydrogenation has been seldom demonstrated. In this work we report the synthesis of sought-after, enantioenriched δ-lactams from oxazolidinone-substituted pyridines and water by an interrupted hydrogenation mechanism.
- Wagener, Tobias,Lückemeier, Lukas,Daniliuc, Constantin G.,Glorius, Frank
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supporting information
p. 6425 - 6429
(2021/02/22)
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- DERIVATIVES OF PIPERLONGUMINE AND USES THEREOF
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The present invention relates to a group of 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one (piperlongumine) derivatives, analogs and pharmaceutically acceptable salts thereof. The present invention also relates to a pharmaceutical composition and formulation containing a derivative of piperlongumine; and use of the derivatives and analogs for treating cancer, reducing inflammation and/or treating an autoimmune or inflammatory disease.
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Paragraph 0958; 0963
(2020/12/13)
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- DERIVATIVES OF PIPERLONGUMINE AND USES THEREOF
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The present invention relates to a group of 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3- dihydropyridin-6-one (piperlongumine) derivatives, analogs and pharmaceutically acceptable salts thereof. The present invention also relates to processes for preparing the same; a pharmaceutical composition and formulation containing a derivative of piperlogumine; and use of the derivatives and analogs for treating cancer.
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Page/Page column 223; 225
(2019/06/11)
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- Carbazole-containing amides and ureas: Discovery of cryptochrome modulators as antihyperglycemic agents
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A series of novel carbazole-containing amides and ureas were synthesized. A structure–activity relationship study of these compounds led to the identification of potent cryptochrome modulators. Based on the desired pharmacokinetic/pharmacodynamic parameters and the results of efficacy studies in db/db mice, compound 50 was selected for further profiling.
- Humphries, Paul S.,Bersot, Ross,Kincaid, John,Mabery, Eric,McCluskie, Kerryn,Park, Timothy,Renner, Travis,Riegler, Erin,Steinfeld, Tod,Turtle, Eric D.,Wei, Zhi-Liang,Willis, Erik
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supporting information
p. 293 - 297
(2018/01/04)
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- Directing Group in Decarboxylative Cross-Coupling: Copper-Catalyzed Site-Selective C-N Bond Formation from Nonactivated Aliphatic Carboxylic Acids
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Copper-catalyzed directed decarboxylative amination of nonactivated aliphatic carboxylic acids is described. This intramolecular C-N bond formation reaction provides efficient access to the synthesis of pyrrolidine and piperidine derivatives as well as the modification of complex natural products. Moreover, this reaction presents excellent site-selectivity in the C-N bond formation step through the use of directing group. Our work can be considered as a big step toward controllable radical decarboxylative carbon-heteroatom cross-coupling.
- Liu, Zhao-Jing,Lu, Xi,Wang, Guan,Li, Lei,Jiang, Wei-Tao,Wang, Yu-Dong,Xiao, Bin,Fu, Yao
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supporting information
p. 9714 - 9719
(2016/08/11)
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- CARBAZOLE-CONTAINING AMIDES, CARBAMATES, AND UREAS AS CRYPTOCHROME MODULATORS
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The subject matter herein is directed to carbazole-containing amide, carbamate, and urea derivatives and pharmaceutically acceptable salts or hydrates thereof of structural formula I wherein the variable R1, R2, R3, R4, R5, R6, R7, A, D, E, G, J, L, M, Q, a, and b are accordingly described. Also provided are pharmaceutical compositions containing the compounds of formula I to treat a Cry-mediated disease or disorder, such as diabetes, complications associated with diabetes, Cushing's syndrome, NASH, NAFLD, asthma, and COPD.
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Paragraph 0299
(2015/10/28)
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- PROCESS FOR PREPARING LACTAMS
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The present invention relates to a method for preparing lactams using heterogeneous catalysis by hydrogenating at least one compound of the following formula (I), where A is a radical of the following formula (I′) or (II′): —CH(R1)—CH(R2)— (I′); or —CH(R1)—CH(R2)—CH(R3)— (II′); where R1, R2 and R3 are, independently from each other, H, OH, an alkyl radical, or a cycloalkyl radical; and R is H or a straight or branched alkyl radical having 1 to 20, preferably 1 to 10, and more preferably 1 to 4 carbon atoms. Said method is carried out at a pressure of less than 60 bars, preferably 10 to 50 bars, in the presence of a solid hydrogenation catalyst including at least two metals selected from the group of noble metals and transition metals, and an inert substance used as a support, wherein said compound of formula (I) can be used alone or as part of a mixture.
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Paragraph 0087; 0088; 0089; 0090; 0091; 0092
(2015/02/25)
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- Oxidant-free conversion of cyclic amines to lactams and H2 using water as the oxygen atom source
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Direct conversion of cyclic amines to lactams utilizing water as the only reagent is catalyzed by pincer complex 2. In contrast to previously known methods of amine-to-amide conversion, this reaction occurs in the absence of oxidants and is accompanied by liberation of H2, with water serving as a source of oxygen atom. Formation of a cyclic hemiaminal intermediate plays a key role in enabling such reactivity. This represents an unprecedented, conceptually new type of amide formation reaction directly from amines and water under oxidant-free conditions.
- Khusnutdinova, Julia R.,Ben-David, Yehoshoa,Milstein, David
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supporting information
p. 2998 - 3001
(2014/03/21)
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- Ring contraction of N-chlorolactams, a novel rearrangement
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Upon photolysis in methylene chloride at -78 °C, different N-chlorolactams underwent a novel ring contraction to the corresponding carbamoyl chlorides, which were converted to the methyl carbamates. The rearrangement is 100% stereoselective, occurring with retention of configuration at the migrating carbon center. The yields of isolated carbamates ranged from 40% to 57%, the other product being the parent lactam, 18% to 38%.
- Drouin, Alexandre,Lessard, Jean
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p. 4285 - 4288
(2007/10/03)
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- An aza-enolate alkylation strategy for the synthesis of α-alkyl-δ-amino esters and α-alkyl valerolactams
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Alkylation of the aza-enolate of valerolactim methyl ether with electrophiles affords α-alkyl lactims that may be hydrolysed under mild acidic conditions to afford their corresponding α-alkyl-δ-amino esters as their hydrochloride salts. Neutralisation of these salts with base results in smooth intramolecular cyclisation to afford their corresponding α-alkyl lactams in excellent yield. Georg Thieme Verlag Stuttgart.
- Taylor, Piers J. M.,Bull, Steven D.,Andrews, Philip C.
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p. 1347 - 1350
(2007/10/03)
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- Cyclic amidine analogs as inhibitors of nitric oxide synthase
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Disclosed herein are compounds of Formula I STR1 and pharmaceutically acceptable salts thereof which have been found useful in the treatment of nitric oxide synthase mediated diseases and disorders, including neurodegenerative disorders, disorders of gastrointestinal motility and inflammation. These disease and disorders include hypotension, septic shock, toxic shock syndrom, hemodialysis, IL-2 therapy such as in cancer patients, cachexia, immunosuppression such as in transplant therapy, autoimmune and/or inflammatory indications including sunburn or psoriasis and respiratory conditions such as bronchitis, asthma, and acure respiratory distress (ARDS), myocarditis, heart failure, atherosclerosis, arthritis, rheumatoid arthritis, chronic or inflammatory bowel disease, ulcerative colitis, Crohn's disease, systemic lupus erythematosis (SLE), ocular conditions such as ocular hypertension and uveitis, type 1 diabetes, insulin-dependent diabetes mellitus and cystic fibrosis. Compounds of Formula I are also usful in the treatment of hypoxia, hyperbaric oxygen convulsions and toxicity, dementia, Sydenham's chorea, Parkinson's disease, Huntington's disease, amyotrophic lateral sclerosis, mulitple sclerosis, Korsakoff's disease, imbecility related to cerebral vessel disorder, ischemic brain edema, sleeping disorders, schizophrenia, depression, PMS, anxiety, drug addiction, pain, migraine, immune complex disease, as immunosupressive agents and for preventing or reversing tolerance to opiates and diazepines.
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- PREPARATION OF LACTAMS VIA OXIDATION OF CYCLIC, TERTIARY AND SECONDARY AMINES WITH Hg(II)-EDTA COMPLEX IN ALKALINE MEDIUM
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Oxidation of N-alkylpiperidines and other cyclic, tertiary amines with Hg(II)-EDTA complex in basic solution yields lactams, similar oxidation of N-hydroxypiperidines gives hydroxamic acids (presumably via nitrones) and oxidation of N-unsubstituted piperidines affords lactams, probably via 1-piperidine trimers.
- Wenkert, Ernest,Angell, E. Charles
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p. 1331 - 1338
(2007/10/02)
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- SYNTHESIS AND REACTIVITY OF METHYL γ-AZIDO BUTYRATES AND ETHYL δ-AZIDO VALERATES AND OF THE CORRESPONDING ACID CHLORIDES AS USEFUL REAGENTS FOR THE AMINOALKYLATION
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The azidoesters 13 and 14 and the corresponding acid chlorides 22 and 23 are shown to be interesting reagents for the nucleophilic and electrophilic aminoalkylation. α-substituted methyl γ-azidobutyrates 13 and ethyl δ-azido valerates 14 are easily accessible by alkylation of the lithium enolates of the parent compounds 13a and 14a respectively.Their chemoselective reduction leads to 3-substituted lactams 18 and 19.The acid chlorides 22 and 23 issued from 13 and 14 react with nucleophilic reagents, i.e. the carbanion of Meldrum acid, trimethylphosphite and n-butylmanganous iodide giving the the ω-azido,β-ketoesters 25 and 26, the ω-azido,α-acylphosphonates 29 and 30 and the ω-azido ketones 38 and 39 respectively in good yields.The treatment of 25 and 26 by Ph3P in anhydrous ether leads to the cyclic β-enaminoesters 27 and 28 whereas the α-acylphosphonates give the cyclic iminophosphonates 33 and 34a in good yields.These cyclizations occur via an intramolecular aza-Wittig reaction.
- Khoukhi, N.,Vaultier, M.,Carrie, R.
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p. 1811 - 1822
(2007/10/02)
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