56366-31-5Relevant academic research and scientific papers
Ready access to 7,8-dihydroindolo[2,3-d][1]benzazepine-6(5H)-one scaffold and analogues via early-stage Fischer ring-closure reaction
Arion, Vladimir B.,Bacher, Felix,Chuang, Hsiang-Yu,Kuznetcova, Irina,Vegh, Daniel
, p. 143 - 151 (2022/02/05)
Paullone isomers are known as inhibitors of tubulin polymerase and cyclin dependent kinases (Cdks), which are potential targets for cancer chemotherapy. Herein we report an efficient and clean pathway to the fourth isomer, which remained elusive so far, namely 7,8-dihydroindolo[2,3-d][1]benzazepin-6(5H)-one. Moreover, we demonstrate the generality of our pathway by synthesizing two closely related analogues, one containing a bromo substituent and the other one incorporating an 8-membered instead of a 7-mem-bered ring. The key transformation in this four-step synthesis, with an overall yield of 29%, is the Fischer indole reaction of 2-nitro-phenylacetyl acetoacetate with 1-benzyl-1-phenylhydrazine in acetic acid that delivers methyl 2-(1-benzyl-3-(2-nitrophenyl)-1H-indol-2-yl)acetate in 55% yield.
CONDENSED CYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
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Paragraph 0425; 0427, (2020/02/29)
A condensed cyclic compound and an organic light-emitting device including the same, the condensed cyclic compound being represented by the following Formula 1:
ORGANIC ELECTROLUMINESCENCE DEVICE AND CONDENSED CYCLIC COMPOUND FOR ORGANIC ELECTROLUMINESCENCE DEVICE
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Paragraph 0115-0117, (2019/12/25)
An organic electroluminescence device of an embodiment includes a first electrode and a second electrode facing each other, and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one organic layer in
Iodine-Mediated Intramolecular Dehydrogenative Coupling: Synthesis of N-Alkylindolo[3,2-c]- and -[2,3-c]quinoline Iodides
Volvoikar, Prajesh S.,Tilve, Santosh G.
supporting information, p. 892 - 895 (2016/03/15)
An I2/TBHP-mediated intramolecular dehydrogenative coupling reaction is developed for the synthesis of a library of medicinally important 5,11-dialkylindolo[3,2-c]quinoline salts and 5,7-dimethylindolo[2,3-c]quinoline salts. The annulation reaction is followed by aromatization to yield tetracycles in good yield. This protocol is also demonstrated for the synthesis of the naturally occurring isocryptolepine in salt form.
NITROGENATED AROMATIC COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL, AND ORGANIC ELECTRONIC DEVICE
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Paragraph 0130; 0132; 0142; 0143, (2013/07/31)
Provided are a nitrogen-containing aromatic heterocyclic compound useful as an organic semiconductor material and an organic electronic device using this compound. The nitrogen-containing aromatic heterocyclic compound has a fused indole skeleton represented by the following formula (1), the organic semiconductor material contains the said compound, and the organic electronic device uses the said organic semiconductor material. In general formula (1), X is N-A', O, S, or Se; A is an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group exclusive of a fused heterocycle consisting of 4 rings or more; and R is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group exclusive of a fused heterocycle consisting of 4 rings or more.
NITROGENATED AROMATIC COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL, AND ORGANIC ELECTRONIC DEVICE
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Paragraph 0149, (2013/09/11)
Provided are a novel nitrogen-containing aromatic heterocyclic compound and an organic electronic device using the compound. This nitrogen-containing aromatic compound is represented by the general formula (1). Further, the present invention relates to or
New route to the synthesis of the isocryptolepine alkaloid and its related skeletons using a modified Pictet-Spengler reaction
Agarwal, Piyush K.,Sawant, Devesh,Sharma, Sunil,Kundu, Bijoy
experimental part, p. 292 - 303 (2009/06/21)
A new route to the synthesis of the isocryptolepine alkaloid with antimalarial activity using a modified Pictet-Spengler reaction has been devised. The strategy was then used to generate libraries based on three structural variants of the alkaloid. Compounds based on these three variants in general were accessed in three steps through a modified Pictet-Spengler cyclization reaction as the key step. The C-2-, C-3-, or N-1-linked (aminoaryl)indoles (8, 12, 13) required for cyclization were obtained by treating the corresponding indoles with o-halonitrobenzene using either nucleophilic re-placement or Pd-based chemistry (Heck/Suzuki reaction) followed by reduction of the nitroaryl functionality. The substrates 8, 12, and 13 were then subjected to the Pictet-Spengler reaction to furnish polycyclic structures, indolo-quinolines 4 and 19 and indolo-quinoxalines 20 with three-point diversity in high yields and purities. One of the indolo-quinolines 4a after treatment with CH3I furnished the isocryptolepine alkaloid in excellent yield. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
Baylis-Hillman reaction of 1-formyl-β-carboline: One-step synthesis of the canthin-6-one framework by an unprecedented cascade cyclization reaction
Singh, Virender,Hutait, Samiran,Batra, Sanjay
scheme or table, p. 6211 - 6216 (2010/03/24)
A one-step access to the canthin-6-one architecture by the Baylis-Hillman reaction of methyl l-formyl-9H-β-carboline3-carboxylate or 1-formyl-9H-β-carboline involving an unprecedented cascade cyclization reaction is reported. Wiley-VCH Verlag GmbH & Co. K
