- Synthesis of a Masked 2,3-Diaminoindole
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A three-step synthesis of masked 2,3-diaminoindole 1 from 2-iodo-3-nitro-1-(phenylsulfonyl)indole (2) has been developed. Treatment of 1 with trifluoroacetic acid generates the unstable 2,3-diamino-1-(phenylsulfonyl)indole (3), which can be trapped with α-dicarbonyl compounds to afford 5H-pyrazino[2,3-b]indoles 7-10.
- Mannes, Philip Z.,Onyango, Evans O.,Gribble, Gordon W.
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- Sulfur-mediated annulation of 1,2-phenylenediamines towards benzofuro- A nd benzothieno-quinoxalines
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We report a method for condensation between ortho-phenylenediamines and ortho-hydroxyacetophenones to afford benzofuroquinoxalines. The reactions proceeded in the presence of an elemental sulfur mediator, DABCO base, and DMSO solvent. Functionalities such as nitrile, ester, and halogen groups were compatible. The conditions could be applicable for the synthesis of benzothienoquinoxalines from ortho-chloroacetophenones.
- Ho, Tuan H.,Nguyen, Tung T.,Phan, Nam T. S.,Phan, Nhu T. A.,Tran, Loan T.
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- Synthesis and blue phosphorescent device performances of a new bipolar host material containing pyrazino[2,3-b]indole moiety
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A new bipolar host material (CzPhPz) consisting of 5H-pyrazino[2,3-b]indole unit was synthesized and its photophysical properties and device performances were investigated. It showed good electron transport properties with a high triplet energy of 2.83 eV. CzPhPz was effective as the host material for FIrpic-based blue PHOLED with a high quantum efficiency of 15.0%. This journal is
- Jang, Hong-Gu,Jeon, Sang Kyu,Lee, Jun Yeob,Hwang, Seok-Ho
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p. 57679 - 57682
(2015/02/02)
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- Synthesis of some diazino-fused tricyclic systems via Suzuki cross-coupling and regioselective nitrene insertion reactions
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Suzuki coupling of 5-chloro-2-methyl-6-phenylpyridazin-3(2H)-one, 6-chloro-1,3-dimethyluracil and 2-chloropyrazine with protected aminoaryl boronic acids resulted in the corresponding pivaloylaminophenyl diazines which were transformed to diazino-fused indole and cinnoline derivatives. Suzuki coupling of 5-amino-6-chloro-1,3-dimethyluracil with 2-formylphenyl boronic acid afforded a novel pyrimidoisoquinoline ring system in a one-pot reaction.
- Tapolcsányi, Pál,Krajsovszky, Gábor,Andó, Rómeó,Lipcsey, Péter,Horváth, Gyula,Mátyus, Péter,Riedl, Zsuzsanna,Hajós, Gy?rgy,Maes, Bert U. W.,Lemière, Guy L. F.
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p. 10137 - 10143
(2007/10/03)
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- A straightforward synthesis of pyridopyrazino[2,3-b]indoles and indolo [2,3-b]-quinoxaline
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1,2-Diamines (ethylenediamine, o-phenylenediamine, 2,3-diamino-pyridine, 3,4-diaminopyridine) were reacted with 1-acetyl-2-bromo-3-indolinone to afford 5H-pyrazino[2,3-b]indoles, indolo[2,3-b]quinoxaline and pyridopyrazino[2,3-b]indole in good yields. Alkylation of the indolic nitrogen atom of these indolic derivatives with 2-chloroethylmorpholine, 2-chloroethyl-dimethylamine and allyl bromide was carried out in order to obtain the corresponding N-alkylated derivatives.
- Alphonse, France-Aimée,Routier, Sylvain,Coudert, Gérard,Mérour, Jean-Yves
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p. 925 - 940
(2007/10/03)
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- Reactions of 3-([(trifiuoromethyl)sulfonyl]oxy)-1H-indole derivatives with diamines and carbon nucleophiles. Synthesis of 6H-indolo[2,3- b]quinoxaline derivatives
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Indolic triflate reacted with 1,2-diamines to afford pyrazino[2,3- b]indole or indolo[2,3-b] quinoxaline. Carbon nucleophiles such as malonate derivatives also reacted with indolic triflate in absence of palladium catalyst to afford 2-(3-oxo-2,3-dihydro-1
- Malapel-Andrieu, Beatrice,Merour, Jean-Yves
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p. 11095 - 11110
(2007/10/03)
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- Synthesis of 5H-pyrazino[2,3-b]indoles from indole-2,3-dione derivatives
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Reaction of N-acetylindol-2,3-diones with ethylenediamines gave the dihydropyrazinones 11, which could, after dehydrogenation and deacetylation, be transformed to the corresponding 5H-pyrazino[2,3-e]indoles 5. N,N-Dimethylaminoethylation of the anion of 5
- Bergman, Jan,Vallberg, Hans
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p. 742 - 752
(2007/10/03)
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- 3-Oxo 3H-Indole from Dioxygen Copper-Catalyzed Oxidation of Indole: One-Flask Synthesis of 2-Dialkylamino 3-Oxo 3H-Indoles.
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Cu(I)Cl-catalyzed oxidation of indole 1 by dioxygen in anhydrous acetonitrile leads to highly reactive 3-oxo 3H-indole 2, which provides directly 2-dialkylamino 3-oxo 3H-indoles 3 in presence of dialkylamines.Amidines 3, previously difficult to prepare, are potentially useful synthons in the field of heterocyclic chemistry. Key Words: Copper-catalyzed oxidation; dioxygen; indole; 2-dialkylamino 3-oxo 3H-indoles.
- Capdevielle, Patrice,Maumy, Michel
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p. 2953 - 2956
(2007/10/02)
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