- Lithiation of 1-alkoxyindole derivatives
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Lithiation of 1-alkoxyindoles, 3-dimethylaminomethyl- and 3-dimethylaminoethyl-1-methoxyindole occurred regioselectively at the 2-position. The introduction of a sterically bulky group into the 2-position of 3-dimethylaminomethyl-1-methoxyindoles directed the lithiation to the 4-position.
- Nakagawa, Kyoko,Kobayashi, Tetsuya,Kawasaki, Toshiya,Somei, Masanori
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p. 968 - 997
(2019/04/26)
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- Synthesis of free NH 2-(aminomethyl)indoles through copper-catalyzed reaction of 3-(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols with amines and palladium/copper- cocatalyzed domino three-component Sonogashira cross-coupling/cyclization/substitu
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Free NH 2-(aminomethyl)indoles have been prepared via copper-catalyzed cyclization of 3-(ortho-trifluoroacetamidophenyl)-1-propargylic alcohols in the presence of primary or secondary amines. The synthesis has been developed into a simple and very efficie
- Cacchi, Sandro,Fabrizi, Giancarlo,Iazzetti, Antonia,Molinaro, Carmela,Verdiglione, Rosanna,Goggiamani, Antonella
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supporting information
p. 1053 - 1059
(2015/03/30)
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- Palladium-catalyzed synthesis of 2-(aminomethyl)indoles from 3-(o -trifluoroacetamidoaryl)-1-propargylic alcohols and amines
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A novel palladium-catalyzed approach to 2-(aminomethyl)indoles from 3-(o-trifluoroacetamidoaryl)-1-propargylic alcohols and amines has been developed.
- Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella,Molinaro, Carmela,Verdiglione, Rosanna
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p. 401 - 407
(2014/01/17)
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- Synthesis of indoles: Tetrahydropyrazino[1,2-a]indole-1,4-dione and pyrazino[1,2-a]indole-6,13-diones from piperazine-2,5-diones
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The readily available piperazine-2,5-dione has been used to prepare both 1:1 (1-3), with stereotopic methylene protons; and 2:1 (4-6) arylmethylenepiperazine-2,5-diones in above average yields. The halo-derivatives, 1, 4 and 5 were cyclized to pyrazino[1,2-a]indoles, 7-9, using copper bronze. Indole compounds 7 and 9 were further treated, separately, with lithium aluminium hydride, sodium borohydride, lithium hydroxide monohydrate and butyl lithium to yield 2-substituted indoles 10-13.
- Akeng'a,Read
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- Palladium-catalyzed heteroannulation with acetylenic carbinols as synthons-synthesis of quinolines and 2,3-dihydro-4(1H)-quinolones
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o-Iodoanilides 4 reacted with terminal acetylenic carbinols 5 under palladium-catalyzed conditions to yield o-substituted anilides 6. Most of the anilides 6 could be cyclized with NaOEt/EtOH to 2-arylquinolines 2. o-Iodoanilines 7 reacted with carbinols 5 leading to 8 which on palladium(II) assisted cyclisation afforded substituted quinolines 2. An excellent synthesis of the alkaloid dubamine (2n) is reported. Also, the anilides 6 on acid-catalyzed rearrangement, deprotection and cyclisation led to the 2-aryl-2, 3-dihydro-4(1H)-quinolones 16.
- Mahanty, Jyan S.,De, Mahuya,Das, Palas,Kundu, Nitya G.
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p. 13397 - 13418
(2007/10/03)
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- Synthesis of Quinolines and 2,3-Dihydro-4(1H)-quinolones. Palladium Catalysed Reaction of o-Iodoanilides with Acetylenic Carbinols
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A facile and general synthesis of quinolines and 2,3-dihydro-4(1H)-quinolones was accomplished through palladium catalysed reaction of o-iodoanilides with acetylenic carbinols.Key Words: quinolines; 2,3-dihydro-4(1H)-quinolones; palladium catalysis; o-iodoanilines; acetylenic carbinols.
- Kundu, Nitya G.,Mahanty, Jyan S.,Das, Palas,Das, Biswajit
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p. 1625 - 1628
(2007/10/02)
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- A REGIOSELECTIVE LITHIATION OF 1-METHOXYMETHOXYINDOLE AT THE 2-POSITION AND ITS APPLICATION FOR THE SYNTHESIS OF 2-SUBSTITUTED INDOLES
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A regioselective lithiation of 1-methoxymethoxyindole at the 2-position was achieved with n-BuLi at 0 deg C.Subsequent treatment with electrophiles afforded 2-substituted 1-methoxymethoxyindoles, which were readily converted to 2-substituted indoles.
- Somei, Masanori,Kobayashi, Tetsuya
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p. 1295 - 1298
(2007/10/02)
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- PREPARATION OF 1-HYDROXYINDOLE DERIVATIVES AND A NEW ROUTE TO 2-SUBSTITUTED INDOLES
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An easy handling method of 1-hydroxyindole is developed.Based on the method, preparation and reaction of 1-hydroxyindole derivatives are investigated.A new regioselective lithiation of 1-methoxyindole and its application for the synthesis of 2-substituted indoles are also reported.
- Kawasaki, Toshiya,Kodama, Atsushi,Nishida, Tokiko,Shimizu, Kazuhisa,Somei, Masanori
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p. 221 - 227
(2007/10/02)
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