- Iron-Catalyzed Oxidative Decarbonylative α-Alkylation of Acyl-Substituted Furans with Aliphatic Aldehydes as the Alkylating Agents
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A protocol for FeCl2-catalyzed oxidative decarbonylative α-alkylation of acyl furans using alkyl aldehydes as the alkylating agents has been developed. This protocol affords α-alkyl-α-acylfurans in moderate to good yields in a practical and sustainable fa
- Luo, Wenkun,Yang, Yongjie,Liu, Bo,Yin, Biaolin
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p. 9396 - 9404
(2020/08/14)
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- Preparation of isoquinazolines: Via metal-free [4 + 2] cycloaddition of ynamides with nitriles
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TfOH-mediated [4 + 2] cycloaddition of ynamides with nitriles to construct 1,2-dihydroquinazolines is realized by a direct reaction in moderate to excellent yields (up to 93%) in a stereospecific manner. A rapid and efficient strategy has been employed for the syntheses of alkyl-substituted 1,2-dihydroquinazoline derivatives, and it exhibits good functional group tolerance, has a short reaction time, shows excellent diastereoselectivity, and is a simple and high-yielding reaction.
- Wu, Hao,Liu, Yu,He, Ming-Xing,Wen, Hao,Cao, Wei,Chen, Ping,Tang, Yu
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p. 8408 - 8416
(2019/09/30)
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- Mechanistic Studies on the Organocatalytic α-Chlorination of Aldehydes: The Role and Nature of Off-Cycle Intermediates
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Herein we report the isolation and characterization of aminal intermediates in the organocatalytic α-chlorination of aldehydes. These species are stable covalent ternary adducts of the substrate, the catalyst and the chlorinating reagent. NMR-assisted kinetic studies and isotopic labeling experiments with the isolated intermediate did not support its involvement in downstream stereoselective processes as proposed by Blackmond. By tuning the reactivity of the chlorinating reagent, we were able to suppress the accumulation of rate-limiting off-cycle intermediates. As a result, an efficient and highly enantioselective catalytic system with a broad functional group tolerance was developed.
- Ponath, Sebastian,Menger, Martina,Grothues, Lydia,Weber, Manuela,Lentz, Dieter,Strohmann, Carsten,Christmann, Mathias
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supporting information
p. 11683 - 11687
(2018/09/10)
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- COMPOUNDS AND RELATED METHODS OF USE
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Described herein are compounds of formula (I), related compositions, and their use, for example in the formation of α-amino acids or a precursor thereof such as an α-aminonitrile.
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Paragraph 0325; 0326
(2013/03/28)
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- Tropylium ion mediated α-cyanation of amines
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Tropylium ion mediated α-cyanation of amines is described. Even in the presence of KCN, tropylium ion is capable of oxidizing various amine substrates, and the resulting iminium ions undergo salt metathesis with cyanide ion to produce aminonitriles. The byproducts of this transformation are simply cycloheptatriene, a volatile hydrocarbon, and water-soluble potassium tetrafluoroborate. Thirteen total substrates are shown for the α-cyanation procedure, including a gram scale synthesis of 17β-cyanosparteine. In addition, a tropylium ion mediated oxidative aza-Cope rearrangement is demonstrated.
- Allen, Julia M.,Lambert, Tristan H.
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supporting information; experimental part
p. 1260 - 1262
(2011/04/15)
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- Practical and efficient method for amino acid derivatives containing β-quaternary center: application toward synthesis of hepatitis C virus NS3 serine protease inhibitors
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A practical and efficient route toward synthesis of amino acid derivatives containing β-quaternary center has been developed using diastereoselective Strecker reaction. The method was employed for preparation of >100 g of β-methylcyclohexyl glycine deriva
- Arasappan, Ashok,Venkatraman, Srikanth,Padilla, Angela I.,Wu, Wanli,Meng, Tao,Jin, Yan,Wong, Jesse,Prongay, Andrew,Girijavallabhan, Viyyoor,George Njoroge
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p. 6343 - 6347
(2008/02/10)
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- HCV NS3 protease inhibitors
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The present invention relates to macrocyclic compounds of formula (I) that are useful as inhibitors of the hepatitis C virus (HCV) NS3 protease, their synthesis, and their use for treating or preventing HCV infections.
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Page/Page column 97
(2008/06/13)
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- The tris(trimethylsilyl)silane/thiol reducing system: A tool for measuring rate constants for reactions of carbon-centered radicals with thiols
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An extension of the well-known 'free-radical-clock' methodology is described that allows one to determine the rate constants of carbon-centered radicals with a variety of thiols by using the tris(trime-thylsilyl)silane/thiol couple as a reducing system. A
- Chatgilialoglu, Chryssostomos
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p. 2387 - 2398
(2007/10/03)
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- NOVEL KETOAMIDES WITH CYCLIC P4'S AS INHIBITORS OF NS3 SERINE PROTEASE OF HEPATITIS C VIRUS
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The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.
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Page/Page column 77
(2008/06/13)
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- NOVEL COMPOUNDS AS INHIBITORS OF HEPATITIS C VIRUS NS3 SERINE PROTEASE
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The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.
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Page/Page column 77
(2008/06/13)
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- CYCLOBUTENEDIONE GROUPS-CONTAINING COMPOUNDS AS INHIBITORS OF HEPATITIS C VIRUS NS3 SERINE PROTEASE
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The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.
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Page/Page column 78-79
(2010/02/14)
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- NOVEL COMPOUNDS AS INHIBITORS OF HEPATITIS C VIRUS NS3 SERINE PROTEASE
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The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.
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Page/Page column 76
(2010/02/14)
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- Synthesis of dibenzofuran-1,4-diones using the D?tz benzannulation
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The chromium Fischer carbene complexes of benzofuran and benzothiophene have been prepared and can be used in D?tz benzannulations with alkynes for the regioselective and converg ent synthesis of dibenzofuran-1,4-dione heterocycles. The use of alkynylboronates led to model systems of the tricyclic ring system of popolohuanone E after oxidation. It would appear that the combination of alkynyl boronates with furan type Fischer carbene complexes leads to substantial amounts (~50%) of protodeboronated products.
- Anderson, James C.,Denton, Ross M.,Hickin, H. Gwen,Wilson, Claire
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p. 2327 - 2335
(2007/10/03)
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- Novel peptides as NS3-serine protease inhibitors of hepatitis C virus
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The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.
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- Rate Constants for the Reaction of Acyl Radicals with Bu3SnH and (TMS)3SiH
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The rate constants for the hydrogen abstraction from Bu3SnH and (TMS)3SiH by acyl radicals have been measured by using competing decarbonylation reactions as timing devices.
- Chatgilialoglu, Chryssostomos,Lucarini, Marco
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p. 1299 - 1302
(2007/10/02)
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- Studies on the chemistry of diols and cyclic ethers-53. Dehydration of 1,1-bishydroxymethylcycloalkanes: A quest for a 1,3-hydride shift
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A study of the sulphuric acid-catalysed dehydrations of 1,1-bishydroxymethyl-cyclopropane, - cyclobutane, - cyclopentane and -cyclohexane (1a-1d) revealed that the product distributions are determined by the relative stabilities of carbenium ions and der kinetic control furnished evidence of a 1,3-hydride shift.
- Molnar, Arpad,Bucsi, Imre,Bartok, Mihaly
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p. 4929 - 4936
(2007/10/02)
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- DIRECT AND CHEMOSELECTIVE CONVERSION OF CARBOXYLIC ACIDS INTO ALDEHYDES
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A new method for the direct conversion of carboxylic acids to aldehydes using N,N-dimethylchloromethyleniminium chloride and tri-t-butoxyaluminum hydride was established.This method provides a convenient way for the chemoselective reduction of carboxylic acids even with such a functional group as halide, ester, nitrile, olefin and ketone.
- Fujisawa, Tamotsu,Mori, Toshiki,Tsuge, Shoichi,Sato, Toshio
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p. 1543 - 1546
(2007/10/02)
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