- One-pot synthesis of pyrrolo[2,1-a]isoquinolines via tandem reactions of vinylselenonium salt, 2-bromoethanones, and isoquinoline
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An convenient and one-pot synthesis of pyrrolo[2,1-a]isoquinolines via the tandem reaction of methyl(phenyl)vinylselenonium salt with isoquinoline and 2-bromoethanones has been developed, which features very mild conditions, available substrates, simple experimental procedures, moderate to good yields, and wide functional group tolerance.
- Li, Yunxia,Liao, Minghong,Liu, Shanshan,Mao, Deshou,Sun, Qi,Tang, E.,Zhao, Yan
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p. 1563 - 1574
(2020/01/28)
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- MACROCYCLIC MCL-1 INHIBITORS AND METHODS OF USE
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The present disclosure provides for compounds of Formula (I) wherein A2, A3, A4, A6, A7, A8, A15, RA, R5, R9, R10A, R10B, R11, R12, R13, R14, R16, W, X, and Y have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions, including cancer. Also provided are pharmaceutical compositions comprising compounds of Formula (I).
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Paragraph 00676; 00679
(2019/03/05)
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- MACROCYCLIC MCL-1 INHIBITORS AND METHODS OF USE
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The present disclosure provides for compounds of formula (I), wherein A2, A3, A4, A6, A7, A8, A15, RA, R5, R9, R10A, R10B, R11, R12, R13, R14, R16, W, X, and Y have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions, including cancer. Also provided are pharmaceutical compositions comprising compounds of formula (I).
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Paragraph 00228
(2019/03/05)
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- Synthesis of vinyl thioethers and bis-thioethenes from calcium carbide and disulfides
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Bis-thioethenes and vinyl thioethers were obtained from the reaction of disulfides and calcium carbide in good to high yields using a simple synthetic procedure and common laboratory setup. The tolerance of the reaction was investigated by the examples of aliphatic, aromatic, heteroaromatic and sesquiterpenic substrates.
- Rodygin, Konstantin S.,Gyrdymova, Yuliya V.,Zarubaev, Vladimir V.
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p. 476 - 478
(2017/10/05)
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- Enantioselective Synthesis of Quaternary α-Amino Acids Enabled by the Versatility of the Phenylselenonyl Group
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A novel Cinchona alkaloid-catalyzed enantioselective conjugate addition of α-alkyl substituted α-nitroacetates to phenyl vinyl selenone was developed. The resulting enantio-enriched α,α-dialkyl substituted α-nitroacetates were subsequently converted to various cyclic and acyclic quaternary α-amino acids, taking advantage of the rich functionalities of the resulting Michael adducts. Novel protocols allowing chemoselective reduction of phenyl selenone to phenyl selenide and reduction of alkyl phenyl selenones to alkanes are also reported.
- Clemenceau, Antonin,Wang, Qian,Zhu, Jieping
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p. 18368 - 18372
(2016/12/16)
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- Catalytic asymmetric formal: γ -allylation of deconjugated butenolides
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A formal γ-allylation of deconjugated butenolides is reported based on a two-step sequence consisting of a catalytic diastereo- and enantioselective vinylogous nucleophilic addition to vinyl sulfones and Julia-Kocienski olefination. This highly modular approach delivers densely functionalized butenolides containing a quaternary stereogenic centre in excellent yield with high enantioselectivity.
- Simlandy, Amit K.,Mukherjee, Santanu
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supporting information
p. 5659 - 5664
(2016/07/06)
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- An efficient metal-free pathway to vinyl thioesters with calcium carbide as the acetylene source
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Chemical reactions involving high-pressure acetylene are not easily performed in a standard laboratory setup. The risk of explosion and technical difficulties drastically complicate the equipment and greatly increase the cost. In this study, we propose th
- Rodygin, Konstantin S.,Ananikov, Valentine P.
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supporting information
p. 482 - 486
(2016/01/30)
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- Synthesis of enantiopure 1,4-dioxanes, morpholines, and piperazines from the reaction of chiral 1,2-diols, amino alcohols, and diamines with vinyl selenones
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The reactions of readily available vinyl selenones with enantiopure 1,2-diols, N-protected-1,2-aminoalcohols, and diamines gave substituted enantiopure 1,4-dioxanes, morpholines, and piperazines, respectively, in good to excellent yields. The same procedu
- Bagnoli, Luana,Scarponi, Catalina,Rossi, Maria Giovanna,Testaferri, Lorenzo,Tiecco, Marcello
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scheme or table
p. 993 - 999
(2011/03/20)
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- Al2O3-Supported Cu-catalyzed electrophilic substitution by PhSeBr in organoboranes, organosilanes, and organostannanes. A protocol for the synthesis of unsymmetrical diaryl and alkyl aryl selenides
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(Figure Presented) Alumina-supported copper sulfate efficiently catalyzes electrophilic substitution in organoborane, organosilanes, and organostannanes by phenylselenium bromide providing a novel and efficient route to the synthesis of unsymmetrical diaryl and alkyl aryl selenides. A series of aryl, alkyl, and heteroaryl phenyl selenides were obtained in high yields. The catalyst is inexpensive, eco- and user-friendly, and recyclable. The mechanism involving Cu-assisted nucleophilic displacement of Br in PhSeBr by mild nucleophiles is described.
- Bhadra, Sukalyan,Saha, Amit,Ranu, Brindaban C.
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experimental part
p. 4864 - 4867
(2010/10/18)
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- Bisannelation with vinylselenoxide: Synthesis of tricyclo[3.2.1.0(2,7)]octane-6-one and its Congeners
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Reaction of kinetic enolate of α'-substituted cyclohexenone derivatives with vinylselenoxides provided tricyclo[3.2.1.0(2,7)]octane-6-one derivatives via domino Michael-Michael-substitution protocol. (C) 2000 Elsevier Science Ltd.
- Hagiwara, Hisahiro,Sakai, Hitoshi,Kirita, Miki,Hoshi, Takashi,Suzuki, Toshio,Ando, Masayoshi
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p. 1445 - 1449
(2007/10/03)
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- Hydrozirconation of acetylenic chalcogenides. Synthesis and reactions of zirconated vinyl chalcogenide intermediates
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Acetylenic tellurides react with Cp2Zr(H)Cl in THF at room temperature to give the α-zirconated vinyl telluride intermediates 39, which react with a wide range of electrophiles to give several types of trisubstituted olefins, such as α-halo vin
- Dabdoub, Miguel J.,Begnini, Mauro L.,Guerrero Jr., Palimecio G.
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p. 2371 - 2400
(2007/10/03)
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- THE REACTIONS OF LITHIOBISPHENYLSELENOMETHANE WITH CHLOROMETHYLTRIMETHYLSILANE AND IODOMETHYLTRIMETHYLSTANNANE: NOVEL 1,1 -AND 1,2-ELIMINATION REACTIONS IN ORGANOSELENIUM/ORGANOTIN CHEMISTRY
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Anomalous and unprecedented 1,1- and 1,2-elimination reactions are reported in the alkylation of lithiobisphenylselenomethane 4 with chloromethyltrimethylsilane and iodomethyltrimethylstannane.
- Sarkar, Tarun K.,Satapathi, Tushar K.
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p. 3333 - 3334
(2007/10/02)
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- Vinyl Selenides and Selenoxides: Preparation, Conversion to Lithium Reagents, Diels-Alder Reactivity, and Some Comparisons with Sulfur Analogues
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A variety of aryl vinyl selenides are prepared by reaction of vinyl Grignard reagents with aryl selenyl bromides or by reductive elimination of the adducts of lithiums with carbonyl compounds.Deprotonation of phenyl vinyl selenide is achieved with LDA at -78 deg C in THF.Vinyl selenides with β-alkyl groups require LiTMP and warmer temperatures (-50 deg C) for complete deprotonation.Allylic lithium reagents were obtained from 1-propenyl and 2-methyl-1-propenyl selenides whereas 1-butenyl or 3-methyl-1-butenyl selenides gave vinyl lithium reagents.Reaction with electrophiles proceeds in good to excellent yield.Primary halides require HMPA to react well.Unhindered carbonyl compounds react without enolization.Deprotonation with LDA is shown to be reversible, and during competitive deprotonation studies with LDA, aryl vinyl sulfides are found to be thermodynamically less acidic than aryl vinyl selenides (KS/Se=0.21 for phenyl vinyl and 0.3 for m-(trifluoromethyl)phenyl vinyl).Deprotonation with LiTMP is shown to be irreversible, and competitive deprotonation studies showed vinyl selenide to be kinetically more acidic as well S/Se=0.37 (phenyl vinyl),0.42 (m-(trifluoromethyl)phenyl vinyl)>.Most studies have shown sulfur compounds to be more acidic. m-(Trifluoromethyl)phenyl allyl sulfide as expected, is more acidic than selenium compound (kS/Se=3.8).Vinyl selenoxides can be prepared with m-chloroperbenzoic acid.They are not thermally stable enough to serve as acetylene equivalents in Diels-Alder reactions.Phenyl vinyl selenide gives a Diels-Alder addition product with 1,4-diphenylisobenzofuran but failed to give cycloaddition products with less reactive dienes.Phenyl vinyl selenoxide does not give a useful yield of lithium reagent upon reaction with amide bases.
- Reich, Hans J.,Willis, William W.,Clark, Peter D.
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p. 2775 - 2784
(2007/10/02)
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