- Efficient synthesis of some new antiproliferative N-fused indoles and isoquinolines via 1,3-dipolar cycloaddition reaction in an ionic liquid
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Syntheses of some new pyrrolo-fused pyrrolo[1,2-a] indole derivatives have been achieved by combining N-allyl-indole-2-carbaldehyde with a variety of N-alkyl-glycine esters as well as tetrahydroisoquinolines in an ionic liquid, triethylammonium acetate (TEAA), a recyclable reaction medium, via intramolecular [3+2] cycloaddition reaction. This new method is highly efficient, and the ionic liquid employed is recyclable. The stereochemistry of all the compounds was confirmed by 2D NMR NOESY and in some cases single crystal X-ray diffraction data. The in vitro screening of all new candidates against various bacterial strains and representative human solid tumor cell lines, A549 (lung), HeLa (cervix), SW1573 (lung), T-47D (breast) and WiDr (colon), revealed that many of them have good antibacterial, antifungal and antitubercular and antiproliferative activities.
- Sutariya, Tushar R.,Labana, Balvantsingh M.,Parmar, Narsidas J.,Kant, Rajni,Gupta, Vivek K.,Plata, Gabriela B.,Padrón, José M.
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- One-pot synthesis of heterocyclic β-chlorovinyl aldehydes using vilsmeier reagent
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3-Chloro-1H-indole-2-carboxaldehydes are obtained in moderate yields by the one-pot reaction of various substituted 2-[(carboxymethyl)amino]benzoic acids (1a-d) using Vilsmeier reagent (DMF/ POCl3). The benzfused acyclic diacide analogous to 1a in which nitrogen was replaced by oxygen and sulfur also underwent the reaction smoothly. 3-Chloro-1H-pyrrole-2,4-dicarboxaldehyde was obtained as the only product by the reaction of N-carboxymethyl β-alanine.
- Majo, Vattoly J.,Perumal, Paramasivan T.
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- Synthesis of some heterocyclic compounds derived from indole as antimicrobial agents
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Recently, indoles are considered interesting heterocyclic compounds due to their wide range of biological activities such as antimicrobial activity. Herein, some new indole derivatives containing heterocyclic moieties were synthesized using 3-chloro-1H-Indole-2-carbaldehyde (1) as a starting material, then allowed to react with compounds containing active methylene under Knoevenagel condensation and afforded the corresponding compounds (2, 3, 9). Also, the compound (1) when allowed to react with hydrazine derivatives gave the corresponding thiosemiccarbazone, semicarbazone, and hydrazone derivatives (4, 5, 6). Reaction of thiosemicarbazone derivatives with α-halognated carbonyl compounds gave the thiazolyl indole derivatives (10, 12a–b). Cyclic chalcones (11a–c) were obtained when compound (10) reacted with different aromatic aldehydes. The structures of all new synthesized compounds were confirmed on the basis of spectral analysis, IR, 1H NMR, 13C NMR, and MS spectroscopy. All synthesized compounds were evaluated for their antimicrobial activity. Compounds (2, 5, 7, 8, 11a, 12a) showed high antibacterial activity and compounds (3, 6, 9, 10, 11a, 12a) showed high antifungal activity.
- Sayed, Mostafa,Kamal El-Dean, Adel M.,Ahmed, Mostafa,Hassanien, Reda
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- An Efficient Ugi-Azide Four-Component Approach for the Preparation of Novel 1-(1H-tetrazol-5-yl)-10-chloro-1,2,3,4-tetrahydropyrazino[1,2-a] Indoles
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The synthesis of novel 1-(1H-tetrazol-5-yl)-10-chloro-1,2,3,4-tetrahydropyrazino[1,2-a] indole derivatives starting from the initially prepared 1-(2-bromoethyl)-3-chloro-1H-indole-2-carbaldehyde is described. A variety of likely biologically relevant pyrazino[1,2-a] indole-based 1,5-disubstituted tetrazoles was obtained in moderate to high yields via an Ugi-azide reaction. These reactions presumably proceed by the imine formation, intramolecular cyclization to iminium ion, and nucleophilic addition tandem reactions, respectively.
- Salahi, Saleh,Ghandi, Mehdi,Abbasi, Alireza
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- Efficient preparation method of 3-substitued-benzo five-membered heterocycle-2-carbonyl compound
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The invention discloses an efficient compounding method of a 3-substitued-benzo five-membered heterocycle-2-carbonyl compound. According to the method, a 3-substitued-benzo five-membered heterocycle-2-alcohol compound is subjected to a halogenated oxidation reaction by a halogenating reagent to generate the corresponding 3-substitued-benzo five-membered heterocycle-2-carbonyl compound. The efficient compounding method has the advantages that raw materials are easy to get, reaction conditions are mild, and reaction selectively and yield are high.
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Paragraph 0059-0061
(2017/08/30)
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- Facile Synthesis of 3-Halobenzo-heterocyclic-2-carbonyl Compounds via in situ Halogenation-Oxidation
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A facile method to synthesize 3-halobenzo-heterocyclic-2-carbonyl compounds is described. Mechanistic studies suggested that a halo-cyclization process, which generated the unstable spiro-acetal transition state and readily convertible to the corresponding carbonyl compound might be involved. Diverse 3-halobenzo-heterocyclic-2-carbonyl compounds could be synthesized with up to 95 % yield in mild conditions with inexpensive starting materials. (Figure presented.).
- Jiang, Xiaojian,Yang, Junjie,Zhang, Feng,Yu, Pei,Yi, Peng,Sun, Yewei,Wang, Yuqiang
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supporting information
p. 2678 - 2683
(2016/09/03)
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- INTRODUCTION OF ACYL SUBSTITUTENTS AT POSITION 2 OF THE INDOLINONE RING
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The acylation of 1-acetyl-3-indolinone at position 2 of the heterocycle was realized by the action of acetic and propionic anhydride in the presence of sulfuric acid.It was shown that the reaction takes place with a high yield through an O-acylation and a Fries rearrangement stage.The Fries rearrangement was used to convert the 1-acetyl-3-hydroxybenzoylindole into 1-acetyl-2-benzoyl-3-indolinone.The same β-diketone and also 1-acetyl-2-(p-chlorobenzoyl)-3-indolinone were obtained by the action of a mixture of acetic anhydride and sulfuric acid on the respective 1-acetyl-2-arylidene- 3-indolinones. 1-Acetyl-3-formyl-3-chloroindole was obtained by the reaction of 1-acetyl-3-indolinone with the Vilsmeier complex obtained from DMFA and phosphorus oxychloride.It was deacylated to 2-formyl-3-chloroindole.
- Velezheva, V. S.,Smushkevich, V. Yu.,Romanova, O. B.,Kurkovskaya, L. N.,Suvorov, N. N.
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p. 2186 - 2193
(2007/10/02)
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