cas 73568-35-1, 2-Chloro-6-bromoquinoline-3-carboxaldehyde

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Synthesis, crystal structure, anticancer and molecular docking studies of quinolinone-thiazolidinone hybrid molecules
A new series of quinolone-thiazolidinone hybrid molecules 8a-o were prepared. Quinoline compounds were synthesized by Meth-Cohn synthesis and were condensed with 2,3-disubstituted thiazolidinone. These molecules were screened for their anticancer activities against MDA-MB-231 and MCF-7 cell line using MTT assay. Potent compounds were tested for their cytotoxicity on normal HEK 293 cell lines and most potent compound was tested for its cell cycle analysis. Molecular docking and molecular dynamic studies were performed on human N-acetyl transferase (hNAT-1) protein using Schrodinger molecular docking toolkit. Compound 8n emerged as potent with IC50 8.16?μM against MDA-MB-231 cell line followed by 8e with IC50 17.68?μM. Compound 8n arrested cell cycle at G2/M phase and was non-toxic to human normal kidney cell line. The potent compound 8n binds well with human NAT-1 protein with remarkable hydrogen bonding and π–π interactions. Molecular dynamic studies of 8n further confirm the target for these molecules. Target quinolinone-thiazolidinones were found to be new class of compounds targeting hNAT-1 and can serve as new lead compounds in drug discovery.
Kumar, Vasantha,Rai, Vaishali M.,Udupi, Vishwanatha,Shivalingegowda, Naveen,Pai, Vinitha R.,Krishnappagowda, Lokanath Neratur,Poojary, Boja
p. 793 - 808
(2021/08/12)

The improvement of photovoltaic performance of quinoline-based dye-sensitized solar cells by modification of the auxiliary acceptors
Three new dyes containing diphenylamine as electron donor, benzene (BIM1), benzothiadiazole (BTD) (BIM2) and N-ethylhexylbenzotriazole (BTZ) (BIM3) as auxiliary electron acceptors, quinoline as π-bridge and cyanoacrylic acid as anchoring group were synthesized in D-A-π-A structure for use in dye-sensitized solar cells (DSSCs). The optical, electrochemical, theoretical and photovoltaic methods were performed to understand the auxiliary acceptor influence on the performance of these dyes. Compared to the other dyes, the DSSC with dye BIM3 slightly increases the open circuit voltage (Voc) owing to the retardation of charge recombination by BTZ. However, replacement of benzene or BTZ by BTD unit causes a large red shift of the absorption spectra, leading BIM2 cell to produce the highest short circuit current density (Jsc). Thus, among the three D-A-π-A dyes, BIM2 is determined to be the most efficient dye, which reached a Voc of 0.627 V and Jsc of 11.53 mA cm–2, corresponding to an overall power conversion efficiency of 5.21 % in the presence of chenodeoxycholic acid (CDCA) as the coadsorbent. These results suggest that the insertion of benzothiadiazole as auxiliary acceptor into quinoline-based D-A-π-A dyes can effectively improve photovoltaic performance of DSSCs.
?i?man, ?lkay,Arkan, Burcu,Arslan, Bar?? Se?kin,Avc?, Davut,Derin, Yavuz,Gezgin, Merve,Nebio?lu, Mehmet,Tutar, Ahmet
(2020/10/07)

Microwave assisted regioselective synthesis of quinoline appended triazoles as potent anti-tubercular and antifungal agents via copper (I) catalyzed cycloaddition
Quinolin-3-yl-methyl-1,2,3-triazolyl-1,2,4-triazol-3(4H)-ones 8j-v were synthesized by click chemistry as an ultimate tactic where [3 + 2] cycloaddition of azides with terminal alkynes has been evolved. Herein, we are inclined to divulge the implication and prevalence of CuSO4·5H2O and THF/water promoted [3 + 2] cycloaddition reactions. The foremost supremacy of this method are transitory reaction times, facile workup, excellent yields (88–92%) with exorbitant purity and regioselective single product formation both under conventional and microwave method. Docking studies illustrated strong binding interactions with enzyme InhA-D148G (PDB ID: 4DQU) by means of high C-score values. The anti-tubercular and antifungal screening of synthesized compounds proclaimed promising activity. The in vitro and in silico studies imply that these triazoles appended quinolines may acquire the ideal structural prerequisites for auxiliary expansion of novel therapeutic agents.
Nesaragi, Aravind R.,Kamble, Ravindra R.,Bayannavar, Praveen K.,Shaikh, Saba Kauser J.,Hoolageri, Swati R.,Kodasi, Barnabas,Joshi, Shrinivas D.,Kumbar, Vijay M.
supporting information

(2021/04/12)

Enantioselective synthesis of functionalized 1,4-dihydropyrazolo-[4′,3′:5,6]pyrano[2,3-: B] quinolines through ferrocenyl-phosphine-catalyzed annulation of modified MBH carbonates and pyrazolones
An enantioselective synthesis of highly functionalized 1,4-dihydropyrazolo[4′,3′:5,6]pyrano[2,3-b]quinolines from modified MBH carbonates and pyrazolones via a chiral phosphine-mediated alkylation/annulation sequence has been realized. The chiral dihydropyrano[2,3-c]pyrazoles bearing bio-active condensed heterocycles were facilely formed in good chemical yields and with high to excellent enantioselectivity by utilizing low catalyst loading.
Li, Jingyi,Ling, Fei,Lu, Yin-Jie,Shao, Bingxuan,Xiao, Xiao,Yang, Zehui,Zhong, Weihui
supporting information
p. 4690 - 4693
(2021/05/19)

Design, synthesis, and molecular docking study of novel quinoline-based bis-chalcones as potential antitumor agents
A novel series of quinoline-based symmetrical and unsymmetrical bis-chalcones was synthesized via a Claisen–Schmidt condensation reaction between 3-formyl-quinoline/quinolone derivatives with acetone or arylidene acetones, respectively, by using KOH/MeOH/H2O as a reaction medium. Twelve of the obtained compounds were evaluated for their in vitro cytotoxic activity against 60 different human cancer cell lines according to the National Cancer Institute protocol. Among the screened compounds, the symmetrical N-butyl bis-quinolinyl-chalcone 14g and the unsymmetrical quinolinyl-bis-chalcone 17o bearing a 7-chloro-substitution on the N-benzylquinoline moiety and 4-hydroxy-3-methoxy substituent on the phenyl ring, respectively, exhibited the highest overall cytotoxicity against the evaluated cell lines with a GI50 range of 0.16–5.45 μM, with HCT-116 (GI50 = 0.16) and HT29 (GI50 = 0.42 μM) (colon cancer) representing best-case scenarios. Notably, several GI50 values for these compounds were lower than those of the reference drugs doxorubicin and 5-FU. Docking studies performed on selected derivatives yielded very good binding energies in the active site of proteins that participate in key carcinogenic pathways.
Insuasty, Daniel,García, Stephanie,Abonia, Rodrigo,Insuasty, Braulio,Quiroga, Jairo,Nogueras, Manuel,Cobo, Justo,Borosky, Gabriela L.,Laali, Kenneth K.
(2021/06/01)

Synthesis of 2-methoxy-3-(thiophen-2-ylmethyl)quinoline containing amino carbinols as antitubercular agents
We have designed and synthesized 2-methoxy-3-(thiophen-2-ylmethyl)quinoline containing amino carbinols as possible anti-tubercular agents to combat the disease. These molecules were synthesized by tethering amino ether linkage with hydroxyl group to diarylquinoline skeleton; hydroxyl and amine chains were engrafted on diaryl ring. They were evaluated against strain (H37Ra) of Mycobacterium tuberculosis and most of compounds showed in vitro antitubercular activity. Two compounds having diaryl quinoline hydroxyl amino ether scaffold and three compounds having diaryl amino alkyl carbinol core showed activities at 6.25 μg/mL. This study explores diaryl carbinol prototype as inhibitor against Mycobacterium tuberculosis.
Karkara, Bidhu Bhusan,Mishra, Shashank Shekhar,Panda, Gautam,Singh, Bhupendra N.
(2020/03/30)

Coupling-Isomerization-Cycloisomerization Reaction (CICIR) – An Unexpected and Efficient Domino Approach to Luminescent 2-(Hydroxymethylene)indenones
A Pd/Cu-catalyzed base mediated domino process of ortho-halo (hetero)aryl carboxaldehydes and propargyl alcohols unexpectedly furnish 2-(hydroxymethylene)indenones in good to excellent yield as a result of a coupling-isomerization-cycloisomerization reaction (CICIR). In addition, the title compounds constitute an interesting class of luminophores with tunable emission solvatochromicity.
Ghazvini, Helya Janatian,Armaghan, Mahsa,Janiak, Christoph,Balalaie, Saeed,Müller, Thomas J. J.
supporting information
p. 7058 - 7062
(2019/11/11)

Synthesis, antibacterial activity and docking studies of substituted quinolone thiosemicarbazones
Fifteen 2-quinolone thiosemicarbazone derivatives of which eleven were new, were synthesized at room temperature. The key intermediate was the quinolone carbaldehyde, from which thiosemicarbazones were formed by the reaction of thiosemicarbazides with the aldehyde moiety. The structures of the synthesized compounds were elucidated by 1D and 2D-NMR spectroscopy and mass spectrometry. The synthesized compounds showed antibacterial activity with MBCs in the range 0.80 to 36.49 mM against Staphylococcus aureus, Staphylococcus aureus Rosenbach (MRSA), Pseudomonas aeruginosa, Klebsiella pneumoniae, Escherichia coli and Salmonella typhimurium. The best activity was seen when a larger halogen such as chlorine and bromine were substituted at C-6 on the quinolone scaffold and when a planar phenyl group was present on the thiosemicarbazone moiety. Activity was reduced when a smaller fluorine atom was present at C-6 or when a methyl group was attached to the thiosemicarbazone. This group of compounds showed a high negative binding affinity, which suggested promising antimcrobial activity. The 6-chloro derivative with a phenyl group on the thiosemicarbazone had the greatest negative binding affinity.
Govender, Hogantharanni,Mocktar, Chunderika,Kumalo, Hezekiel M.,Koorbanally, Neil A.
p. 1074 - 1081
(2019/06/10)

Discovery and optimization of thienopyridine derivatives as novel urea transporter inhibitors
Urea transporters (UTs) play an important role in the urine concentrating mechanism and are recognized as novel targets for developing small molecule inhibitors with salt-sparing diuretic activity. Thienoquinoline derivatives, a class of novel UT-B inhibitors identified by our group, play a significant diuresis in animal model. However, the poor solubility and low bioavailability limited its further development. To overcome these shortcomings, the structure modification of thienoquinoline was carried out in this study, which led to the discovery of novel thienopyridine derivatives as specific urea transporter inhibitors. Further optimization obtained the promising preclinical candidate 8n with not only excellent inhibition effect on urea transporters and diuretic activity on rat model, but also suitable water solubility and Log P value.
Zhao, Yan,Li, Min,Li, Bowen,Zhang, Shun,Su, Aoze,Xing, Yongning,Ge, Zemei,Li, Runtao,Yang, Baoxue
p. 131 - 142
(2019/04/08)

Tetrazolylmethyl quinolines: Design, docking studies, synthesis, anticancer and antifungal analyses
A new series of 2,5 and 1,5-regioisomers of the tetrazolyl group viz., 3-[(5-benzyl/benzylthio-2H-tetrazol-2-yl) methyl]-2-chloro-6-substituted quinoline 6h-q and 3-[(5-benzyl/benzylthio-1H-tetrazol-1-yl) methyl]-2-chloro-6-substituted quinolines 7h-q were synthesized. Docking studies of all these compounds with DNA as target using PDB: 1AU5 and 453D revealed that the compounds 6h and 6i act as covalent cross linker on the DNA helix of the former and intercalate the latter both with higher C score values. Another set of docking studies in the active pocket of dihydrofolate reductase and N-myristoyl transferase as targets to assess antifungal activity revealed that compounds 6k, 6l, 6p and 7q (with bromo and fluro substituents) showcases different binding modes and hydrogen bonding. Further, the compounds were screened for anticancer activity (primary cytotoxicity) against NCI-60 Human tumor cell line at a single high dose (10?5M) concentration assay. Among the tested compounds, 6h has shown 99.28% of GI against Melanoma (SK-MEL-5) and compound 6i has shown 97.56% of GI against Breast Cancer (T-47D). Further, in vitro antifungal assay against A. fumigatus and C. albicans for these compounds 6h-q and 7h-q revealed potential to moderate activities as compared to the standard.
Shaikh, Saba Kauser J.,Kamble, Ravindra R.,Somagond, Shilpa M.,Devarajegowda,Dixit, Sheshagiri R.,Joshi, Shrinivas D.
supporting information
p. 258 - 273
(2017/02/15)

A Schmidt rearrangement-mediated synthesis of novel tetrahydro-benzo[1,4]diazepin-5-ones as potential anticancer and antiprotozoal agents
Novel tetrahydro-5H-benzo[e][1,4]diazepin-5-ones, several of them, containing the quinoline pharmacophore, were synthesized via a Schmidt rearrangement from their corresponding 1,2,3,4-tetrahydro-4-quinolones mediated by the NaN3/H2SO4 reaction conditions. Twelve of the obtained compounds were in vitro screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines, where compound 24a presented a remarkable activity against 58 of the 60 cancer cell lines, with the most important GI50 values ranging from 0.047 to 8.16 μM and LC50 values ranging from 9.4 to > 100 μM. Additionally, some of them were evaluated as antimalarial, antitrypanosomal and antileishmanial agents. The best antimalarial response was observed for compound 22g with an EC50 = 13.61 μg/mL for Plasmodium falciparum, while compound 24d exhibited high activity against Trypanosoma cruzi. and Leishmania (V) panamensis with EC50 = 2.78 μg/mL and 3.35 μg/mL respectively.
Insuasty, Daniel,Robledo, Sara M.,Vélez, Iván D.,Cuervo, Paola,Insuasty, Braulio,Quiroga, Jairo,Nogueras, Manuel,Cobo, Justo,Abonia, Rodrigo
p. 567 - 583
(2017/11/03)

Modified procedure for the synthesis of 2-chloroquinoline-3-carbaldehydes using phosphorus pentachloride
An alternative, convenient, and efficient procedure for the synthesis of 2-chloroquinoline-3-carbaldehyde was carried out by the action of Vilsmeiers reagent on acetanilides using phosphorus pentachloride as chlorinating agent in place of phosphoryl chloride, obtaining good yields for activated acetanilides. The optimal conditions for this reaction requires only 4.5 equivalents of phosphorus pentachloride, 3 equivalents of N,N-dimethylformamide, and 1 equivalent of the corresponding acetanilide at 100 °C for approximately 4 h.
Romero, Angel H.
supporting information
p. 287 - 291
(2016/03/09)

2,4,6-Trichloro-1,3,5-triazine and N,N′-dimethylformamide as an effective Vilsmeier-Haack reagent for the synthesis of 2-chloro-3-formyl quinolines from acetanilides
TCTA-DMF (2,4,6-trichloro-1,3,5-triazine/N,N′-dimethylformamide) adduct has been used as a Vilsmeier-Haack type reagent for effective synthesis of 2-chloro-3-formyl quinolines from acetanilides under conventional and ultrasonically assisted conditions. The reaction times under sonication are quite significantly shorter than conventional methods even though the yields obtained under sonication are comparable with those obtained under reflux conditions.
Venkanna,Rajanna,Satish Kumar,Bismillah Ansari, Mohd.,Moazzam Ali
supporting information
p. 5164 - 5167
(2015/08/19)

Design, synthesis of quinolinyl Schiff bases and azetidinones as enoyl ACP-reductase inhibitors
New series of quinoline derivatives were synthesized from 2-chloroquinoline-3-carbaldehydes. In the reaction sequence, substituted acetanilides were cyclized to give 2-chloroquinoline-3-carbaldehydes 2a-d, which were transformed to 6a-d, which were then c
Joshi, Shrinivas D.,More, Uttam A.,Parkale, Deepak,Aminabhavi, Tejraj M.,Gadad, Andanappa K.,Nadagouda, Mallikarjuna N.,Jawarkar, Rahul
p. 3892 - 3911
(2015/10/06)

Synthesis of new 3-(2-Chloroquinolin-3-yl)-5-phenylisoxazole derivatives via click chemistry approach
Herein, we report the synthesis of new substituted 3-(2-chloroquinolin-3- yl)-5-phenylisoxazole (3a-j) by click chemistry in good to moderate yields. This approach is based on the regioselective copper(I)-catalyzed cycloaddition between different nitrile oxides derived from 2-chloroquinoline- 3-carbaldehyde (2a-j) and phenylacetylene. Finally these derivatives were screened for their antibacterial evaluation in vitro against three Gram-negative clinical bacteria: Escherichia coli, Pseudomonas aeruginosa and Acinetobacter baumannii using standard methods.
Ferna?ndez-Galleguillos, Carlos,Saavedra, Luis A.,Gutierrez, Margarita
p. 365 - 371
(2014/02/14)

Efficient synthesis of novel pyranoquinoline derivatives from simple acetanilide derivatives: Experimental and theoretical study of their physicochemical properties using DFT calculations
A convenient reaction of 2-chloroquinoline-3-carbaldehyde derivatives and dimedone in the presence of KF-Al2O3 for the synthesis of useful pyranoquinolines is described. Reasonable yields (41-50percent), easily available starting materials and less expensive efficient catalyst are the key features of the present method. A mechanism was proposed for the reaction course. Attribution of the chemical shifts was made with the help of the density functional theory (DFT) calculations. The computed nuclear magnetic resonance (NMR) chemical shifts are in good agreement with available experimental data. The nucleus-independent chemical shift (NICS) values were used as quantitative measures for the relative aromatic character in pyranoquinolines. The calculated NICS values obtained for the phenyl group of pyranoquinoline compounds are smaller than that of benzene. ?2014 Sociedade Brasileira de Qui?mica.
Mirjafary, Zohreh,Saidian, Hamid,Sahandi, Morteza,Shojaei, Leila
p. 1253 - 1260
(2014/08/05)

Synthesis and 3D-QSAR analysis of 2-chloroquinoline derivatives as H 37 RV MTB inhibitors
Frequency of tuberculosis is progressively increasing worldwide. New emerging strains of bacilli that are emerging are resistant to the currently available drugs which make this issue more alarming. In this regard, a series of substituted quinolinyl chalcones, quinolinyl pyrimidines, and pyridines were synthesized and evaluated for their antitubercular activity in vitro against Mycobacterium tuberculosis H37RV. To establish the role of the 2-chloroquinoline nucleus as a pharmacophoric group and study its influence on the antimycobacterial activity, a 3D-QSAR study based on CoMFA and CoMSIA was undertaken on this set of 2-chloroquinoline derivatives. Statistically significant models that are able to well correlate the antimycobacterial activity with the chemical structures of the 2-chloroquinolines have been developed. The contour maps resulting from the best CoMFA and CoMSIA models were used to identify the structural features relevant to the biological activity in this series of analogs. Further analysis of these interaction-field contour maps also showed a high level of internal consistency. The information obtained from the field 3-D contour maps may be fruitfully utilized in the design of more potent 2-chloroquinoline-based analogs as potential antitubercular candidates. A series of 1 chloroquinoline bearing pyridine and pyrimidine ring system and fluoro/bromo at C-3 and C-6 of the quinoline ring were synthesized and evaluated for their antimycobacterial activity. The MIC data of antitubercular activity was performed for 3D QSAR analysis.
Khunt, Ranjan C.,Khedkar, Vijay M.,Coutinho, Evans C.
p. 669 - 684
(2014/01/06)

Synthesis, characterization and antimicrobial activity of imidazole derivatives
A series of oxazole and their imidazole derivatives were prepared from 6-bromo-2-chloro-3-formylquinoline. The structures of all the synthesized compounds were elucidated by elemental, IR, 1H NMR, 13C NMR spectra. They were assayed in vitro for their anti
Parab,Dixit,Desai
experimental part
p. 2725 - 2728
(2012/01/13)

From fragment screening to in vivo efficacy: Optimization of a series of 2-aminoquinolines as potent inhibitors of beta-site amyloid precursor protein cleaving enzyme 1 (bace1)
Using fragment-based screening of a focused fragment library, 2-aminoquinoline 1 was identified as an initial hit for BACE1. Further SAR development was supported by X-ray structures of BACE1 cocrystallized with various ligands and molecular modeling studies to expedite the discovery of potent compounds. These strategies enabled us to integrate the C-3 side chain on 2-aminoquinoline 1 extending deep into the P2′ binding pocket of BACE1 and enhancing the ligand's potency. We were able to improve the BACE1 potency to subnanomolar range, over 106-fold more potent than the initial hit (900 μM). Further elaboration of the physical properties of the lead compounds to those more consistent with good blood-brain barrier permeability led to inhibitors with greatly improved cellular activity and permeability. Compound 59 showed an IC50 value of 11 nM on BACE1 and cellular activity of 80 nM. This compound was advanced into rat pharmacokinetic and pharmacodynamic studies and demonstrated significant reduction of Aβ levels in cerebrospinal fluid (CSF).
Cheng, Yuan,Judd, Ted C.,Bartberger, Michael D.,Brown, James,Chen, Kui,Fremeau Jr., Robert T.,Hickman, Dean,Hitchcock, Stephen A.,Jordan, Brad,Li, Vivian,Lopez, Patricia,Louie, Steven W.,Luo, Yi,Michelsen, Klaus,Nixey, Thomas,Powers, Timothy S.,Rattan, Claire,Sickmier, E. Allen,St. Jean Jr., David J.,Wahl, Robert C.,Wen, Paul H.,Wood, Stephen
experimental part
p. 5836 - 5857
(2011/10/09)

AMINO HETEROARYL COMPOUNDS AS BETA-SECRETASE MODULATORS AND METHODS OF USE
The present invention comprises a new class of compounds useful for the modulation of Beta-secretase enzyme activity and for the treatment of Beta-secretase mediated diseases, including Alzheimer?s disease (AD) and related conditions. In one embodiment, the compounds have a general Formula I wherein ring A, B1, B2, B3, L, R1, R4, R5 and m of Formula I are defined herein. The invention also includes use of these compounds in pharmaceutical compositions for treatment, prophylactic or therapeutic, of disorders and conditions related to the activity of beta-secretase protein. Such disorders include, for example, Alzheimer?s Disease (AD), cognitive deficits, cognitive impairment, schizophrenia and other central nervous system conditions related to and/or caused by the formation and/or deposition of plaque on the brain. The invention also comprises further embodiments of Formula I, intermediates and processes useful for the preparation of compounds of Formula I
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Page/Page column 35

(2011/06/19)

AMINO HETEROARYL COMPOUNDS AS BETA-SECRETASE MODULATORS AND METHODS OF USE
The present invention comprises a new class of compounds useful for the modulation of Beta-secretase enzyme activity and for the treatment of Beta-secretase mediated diseases, including Alzheimer's disease (AD) and related conditions. In one embodiment, t
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Page/Page column 46-47

(2011/06/19)

Synthesis and antimicrobial activity of pyrazolo [3,4-b] quinolines containing pyrimidine moiety
Various 2-chloroquinoline-3-carbaldehyde-3-(6-p-anisyl-5-cyano-3-N-methyl- 3,4-dihydro pyrimidin-4-one-2-yl) hydrazones4(a-d) have been synthesized by condensation of 6-p-anisyl-5-cyano-2-hydrazino-3-N-methyl-3,4-dihydropyrimidine- 4-one with different 2-chloroquinoline-3-carbaldehydes. The hydrazones on cyclization with DMF/KOH furnished 1-(6-p-anisyl-5-cyano-3-N-methyl-3,4- dihydropyrimidin-4-one-2-yl) pyrazolo [3,4-b] quinolines 5(a-d). All the synthesized compounds were characterized on the basis of IR, 1H NMR and mass spectral data and screened for their antimicrobial activity.
Joshi,Hallikeri,More, Uttam A.,Basavaraj,Kulkarni
p. 69 - 72
(2013/09/24)

Synthesis and antimicrobial activity of some 5-substituted-3-phenyl-N β-(substituted-2-oxo-2H-pyrano[2,3-b]quinoline-3-carbonyl) -1H-indole-2-carboxyhydrazide
Ethyl 3-oxo-3-{2-[(5-substituted-3-phenyl-1H-indol-2-yl)carbonyl] hydrazinyl}propanoates 5a-b were synthesized according to the literature method. These on further reaction with substituted-2-hydroxy-3-formylquinolines 3a-e yielded 5-substituted-Nβ-(2-oxo-2H-pyrano[2,3-b]quinoline-3- carbonyl)-3-phenyl-1H-indole-2-carbohydrazides 6a-j. Structures of the all the newly synthesized compounds were confirmed by spectral data. All these compounds have been screened for their antibacterial activity against Staphylococcus aureus, Escherichia coli and Bacillus subtilus, antifungal activity against Aspergillus niger and Candida albicans and antituberculosis activity against Mycobacterium tuberculosis (H37Rv).
Mathada, Basavarajaiah Suliphal Devara,Mathada, Mruthyunjayaswamy Bennikallu Hire
experimental part
p. 557 - 560
(2009/12/25)

Vilsmeier-Haack reagent: A facile synthesis of 2-chloro-3-formylquinolines from N-arylacetamides and transformation into different functionalities
A simple and regioselective synthesis of 2-chloro-3-formylquinolines through Vilsmeier-Haack cyclisation of N-arylacetamides has been reported. The cyclisation is facilitated by N-arylacetamides bearing electron donating groups at m-position. However, yields of quinolines having electron donating groups are good in all cases. Further, the nucleophilic substitution reaction of the quinolines is also investigated. Similarly, the formyl group in the quinolines is subjected to further transformation into cyano (CAN-NH3) and alkoxycarbonyl (NIS-K2CO3/alcohols) groups to afford corresponding 3-cyano and 3-alkoxycarbonylquinolines, respectively.
Srivastava, Ambika,Singh
p. 1868 - 1875
(2007/10/03)

Ultrasonically accelerated vilsmeier haack cyclisation and formylation reactions
Ultrasonically irradiated Vilsmeier Haack (VH) reaction with acetanilides, hydrocarbons and acetophenones exhibited dramatic rate enhancements with excellent yields. The VH reaction with acetanilides afforded 2-chloro-3-formyl quino-line derivatives, hydrocarbons underwent formylation while hydroxy acetophenones yielded 3-formyl chromones.
Moazzam Ali, Mir,Sana, Sariah,Tasneem,Rajanna,Saiprakash
p. 1351 - 1356
(2007/10/03)

An efficient and facile synthesis of 2-chloro-3-formyl quinolines from acetanilides in micellar media by Vilsmeier-Haack cyclisation
Acetanilides efficiently undergo Vilsmeier Haack cyclisation in micellar media to afford 2-chloro-3-formyl quinoline derivatives in good yields. This procedure works efficiently in CTAB (cetyl trimethyl ammonium bromide), SDS (sodium dodecyl sulphate) and TX (Triton-X-100) media under reflux conditions particularly from deactivated acetanilides in good yields.
Ali,Tasneem,Rajanna,Sai Prakash
p. 251 - 253
(2007/10/03)

Studies on Vilsmeier-Haack reaction. A new route to 2-chloroquinoline-3-carboxyaldehydes an a furoquinoline derivative
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Pawar,Bajare,Mundade
p. 685 - 686
(2007/10/02)

STUDIES ON THE VILSMEIER-HAACK REACTION. REACTION OF SUBSTITUTED ACETOPHENONE OXIMES
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Pawar, Ramrao A.
p. 568
(2007/10/02)

A Versatile New Synthesis of Quinolines and Related Fused Pyridines. Part 5. The Synthesis of 2-Chloroquinoline-3-carbaldehydes
Acetanilides are converted into 2-chloroquinoline-3-carbaldehydes in good yield by the action of Vilsmeier's reagent in phosphoryl chloride solution.The reaction is shown to involve successive conversion of the acetanilide into an imidoyl chloride and then an N-(α-chlorovinyl)aniline.The latter enamine is diformylated at its β-position and subsequently cyclised to the chloroquinolinecarbaldehyde.The diformylated intermediates may be isolated in several cases and separately cyclised with polyphosphoric acid.
Meth-Cohn, Otto,Narine, Bramha,Tarnowski, Brian
p. 1520 - 1530
(2007/10/02)