- Mono-selective β-C-H arylation of: N -methylated amino acids and peptides promoted by the 2-(methylthio)aniline directing group
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2-(Methylthio)aniline (MTA) directed C(sp3)-H functionalisations are efficient and straightforward protocols for the selective β-modification of N-methylated amino acids. The decreased reactivity of MTA in comparison with the 8-aminoquinoline (AQ) directing group allows for selective monoarylations in high yields without the formation of side products. The protocol is also suitable for the introduction of highly functionalised side chains onto the C-terminal alanines of dipeptides. The MTA directing group can easily be removed, providing free carboxylic acids as valuable building blocks.
- Kinsinger, Thorsten,Kazmaier, Uli
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p. 5595 - 5600
(2019/06/13)
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- SELECTIVE INHIBITORS OF CLINICALLY IMPORTANT MUTANTS OF THE EGFR TYROSINE KINASE
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The present invention provides compounds of Formula (I) or a subgeneric structure or species thereof, or a pharmaceutically acceptable salt, ester, solvate, and/or prodrug thereof, and methods and compositions for treating or ameliorating abnormal cell proliferative disorders, such as cancer, wherein A, R2, R3, R10, E1, E2, E3, Y, and Z are as defined herein.
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- Practical and efficient ipso-iodination of arylboronic acids via KF/I2 system
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A facile and effective iododeboronation of variously substituted aryl and heteroarylboronic acids through activation and subsequent ipso-introduction of iodine is presented. The use of KF and I2 at 80 °C in 1,4-dioxane furnishes iodinated compounds in high yields.
- Tramutola, Francesco,Chiummiento, Lucia,Funicello, Maria,Lupattelli, Paolo
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p. 1122 - 1123
(2015/02/19)
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- Convenient synthesis of bis(3-indolyl)-acetylene via Sonogashira coupling
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We describe the synthesis of bis(3-indolyl)acetylene 6 via a Pd-catalyzed cross-coupling reaction of iodoindole 8 and 3-indolylacetylene 9, followed by deprotection of 14 to furnish 6. Copyright Taylor & Francis Group, LLC.
- Roy, Sudipta,Gribble, Gordon W.
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p. 829 - 837
(2008/02/01)
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- A simple iodination protocol via in situ generated ICl using NaI/FeCl 3
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A novel iodination of silyl-enol ethers using hitherto unexplored NaI/FeCl3 system is reported. The procedure has been extended to the iodination of aromatic and hetero aromatic compounds.
- Mohanakrishnan, Arasambattu K.,Prakash, Chandran,Ramesh, Neelamegam
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p. 3242 - 3247
(2007/10/03)
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- Synthesis of indole analogs of 1-benzyl-3-(5'-hydroxymethy 1-2' -furyl) indazole (YC-1) as anti-platelet agents
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The present invention synthesizes a series of novel indole analogs of 1-benzyl-3-(5′-hydroxymethyl-2′-furyl)indazole (YC-1), and their anti-platelet activity.
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Page/Page column 3
(2010/11/30)
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- Facile and inexpensive entry to indeno[2,1-b]indol-6-one nucleus
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Starting from simple indole, a straightforward and inexpensive four-step synthetic approach to indeno[2,1-b]indol-6-one nucleus is described. Copyright Taylor & Francis, Inc.
- Abbiati, Giorgio,Canevari, Valentina,Rossi, Elisabetta,Ruggeri, Alberto
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p. 1845 - 1850
(2007/10/03)
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- Development of highly stereoselective asymmetric 6π- azaelectrocyclization of conformationally flexible linear 1-azatrienes. From determination of multifunctional chiral amines, 7-alkyl cis-1-amino-2-indanols, to application as a new synthetic strategy: Formal synthesis of 20-epiuleine
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The highly stereoselective asymmetric 6π-azaelectrocyclization was achieved as a general synthetic method based on the reaction between the (E)-3-carbonyl-2,4,6-trienal compounds and the (-)-7-alkyl-cis-l-amino-2-indanol derivatives which are effective chiral amines. The 7-alkyl-substituted 2-indanol moiety of the cyclized products was efficiently removed by the novel manganese dioxide oxidation under remarkably mild conditions, and the method was successfully applied to the formal synthesis of optically active 20-epiuleine.
- Tanaka, Katsunori,Kobayashi, Toyoharu,Mori, Hajime,Katsumura, Shigeo
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p. 5906 - 5925
(2007/10/03)
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- Rapid route to 3,4-substituted indoles via a directed ortho metalation-retro-Mannich sequence.
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[reaction: see text] In the presence of NXS (X = Br, I, Cl), gramine derivatives 1, derived by combined directed ortho metalation (DoM)-cross-coupling sequences, rapidly undergo retro-Mannich fragmentation (2) to afford 3-halo indoles 3 in 37-88% yields.
- Chauder, Brian,Larkin, Andrew,Snieckus, Victor
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p. 815 - 817
(2007/10/03)
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- Bis-Suzuki reactions of 2,3-dihaloindoles. A convenient synthesis of 2,3-diarylindoles
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A convenient, one-pot synthesis of 2,3-diarylindoles 4 is described via a bis-Suzuki palladium-catalyzed cross coupling of 2,3-dihalo-1-(phenylsulfonyl)indoles 1 with arylboronic acids 2, followed by cleavage of the N-protecting group to give 4. The anti-inflammatory drug indoxole (4c) is prepared in high yield. (C) 2000 Elsevier Science Ltd.
- Liu,Gribble
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p. 8717 - 8721
(2007/10/03)
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- A mild and effective iodination method using iodine in the presence of bis-(trifluoroacetoxy)iodobenzene
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Herein is described a mild and effective iodination method using bis(trifluoroacetoxy)iodobenzene iodine as reagent to be applied to electron deficient heterocyclic systems (protected indoles coumarin...). Moreover, sensitive protecting groups such as acetyl and tert butyldimethylsilyl were found to be stable under the new iodination reaction conditions.
- Benhida, Rachid,Blanchard, Pierre,Fourrey, Jean-Louis
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p. 6849 - 6852
(2007/10/03)
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- Synthetic use of 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one: Iodination of aromatic rings
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Treatment of various aromatic compounds with 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one 1A and iodine gave the corresponding iodinated compounds in good yields. Similarly, chlorination and bromination proceeded effectively. As compared with other trivalent iodine compounds, the iodinane 1A showed the best reactivity as a halogenation reagent.
- Muraki, Takahito,Togo, Hideo,Yokoyama, Masataka
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p. 286 - 288
(2007/10/03)
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- Preparation and palladium-catalysed arylation of indolylzinc halides
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Indolylzinc halides are prepared by two methods: transmetallation of indolyllithiums with zinc chloride and oxidative addition of active zinc to iodoindoles. The palladium-catalysed reaction of the indolylzinc halides provides a practical method for synthesizing arylindoles.
- Sakamoto, Takao,Kondo, Yoshinori,Takazawa, Nobuo,Yamanaka, Hiroshi
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p. 1927 - 1934
(2007/10/03)
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- APPROACHES TO THE GENERATION OF 2,3-INDOLYNE
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Several unsuccessful attempts to generate and trap 1-phenylsulfonyl2,3-indolyne (4) from lithio-3-bromo-1-phenylsulfonylindole (9) and 2-lithio-3-iodo-1-phenylsulfonylindole (12), generated by different methods, are described.The remarkable stability of 9
- Conway, Samuel C.,Gribble, Gordon W.
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p. 2095 - 2108
(2007/10/02)
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- A NEW CARBON-CARBON BOND FORMING REACTION IN INDOLE CHEMISTRY. C3-ARYLATION AND ALKYLATION WITH PHENYL (β-INDOLYL)IODONIUM TRIFLUOROACETATE
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Phenyl(β-indolyl)iodonium trifuoroacetate was reacted with various alkyl and aryllithiums (CH3, n-C4H9, C3H5, C6H5) in BF3Et2O/THF to yield C3-alkylation and arylation of the indole nucleus with reductive elimination of iodobenzene.
- Moriarty, Robert M.,Ku, Y. Y.,Sultana, M.,Tuncay, Atilla
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p. 3071 - 3074
(2007/10/02)
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- Generation and Reactions of 3-Lithio-1-(phenylsulfonyl)indole
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Treatment of 1-(phenylsulfonyl)-3-iodoindole (6) with 2 equiv of tert-butyllithium (-100 deg C THF) generates essentially quantitatively 3-lithio-1-(phenylsulfonyl)indole (1).Quenching 1 with various electrophiles gives 3-substituted indoles in good yield
- Saulnier, Mark G.,Gribble, Gordon W.
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p. 757 - 761
(2007/10/02)
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