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Journal articles on the topic 'Indole-2'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Elmakki, Mohammed A. E., Orbett Teboho Alexander, Gertruida J. S. Venter, Johan Andries Venter, and Andreas Roodt. "Structural Study of Model Rhodium(I) Carbonylation Catalysts Activated by Indole-2-/Indoline-2-Carboxylate Bidentate Ligands and Kinetics of Iodomethane Oxidative Addition." Inorganics 10, no. 12 (2022): 251. http://dx.doi.org/10.3390/inorganics10120251.

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The rigid-backbone bidentate ligands Indoline-2-carboxylic acid (IndoliH) and Indole-2-carboxylic acid (IndolH) were evaluated for rhodium(I). IndoliH formed [Rh(Indoli)(CO)(PPh3)] (A2), while IndolH yielded the novel dinuclear [Rh1(Indol’)(CO)(PPh3)Rh2(CO)(PPh3)2] (B2) complex (Indol’ = Indol2−), which were characterized by SCXRD. In B2, the Rh1(I) fragment [Rh1(Indol’)(CO)(PPh3)] (bidentate N,O-Indol) exhibits a square-planar geometry, while Rh2(I) shows a ‘Vaska’-type trans-[O-Rh2(PPh3)2(CO)] configuration (bridging the carboxylate ‘oxo’ O atom of Indol2−). The oxidative addition of MeI to

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2

Sharma, Upendra, Inder Kumar, and Rakesh Kumar. "Recent Advances in the Regioselective Synthesis of Indoles via C–H Activation/Functionalization." Synthesis 50, no. 14 (2018): 2655–77. http://dx.doi.org/10.1055/s-0037-1609733.

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Indole is an important heterocyclic motif that occurs ubiquitously in bioactive natural products and pharmaceuticals. Immense efforts have been devoted to the synthesis of indoles starting from the Fisher indole synthesis to the recently developed C–H activation/functionalization-based methods. Herein, we have reviewed the progress made on the regioselective synthesis of functionalized indoles, including 2-substituted, 3-substituted and 2,3-disusbstituted indoles, since the year 2010.1 Introduction2 Metal-Catalyzed Synthesis of 2-Substituted Indoles3 Metal-Catalyzed Synthesis of 3-Substituted

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3

Kumar, Anil, and Ganesh Shelke. "Sc(OTf)3-Catalyzed Oligomerization of Indole: One-Pot Synthesis of 2-[2,2-Bis(indol-3-yl)ethyl]anilines and 3-(Indolin-2-yl)indoles." Synthesis 49, no. 18 (2017): 4321–26. http://dx.doi.org/10.1055/s-0036-1588181.

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Oligomerization of substituted indoles and N-methylindoles was investigated in the presence of catalytic amounts of scandium triflate in dichloromethane. Two types of indole oligomer, 2-[2,2-bis(indol-3-yl)ethyl]anilines and 3-(indolin-2-yl)indoles were obtained based on the substituent on indole ring. This study constitutes the first example of Sc(OTf)3-catalyzed oligomerization of indoles and gave good yield of 2-[2,2-bis(indol-3-yl)ethyl]anilines and 3-(indolin-2-yl)indoles.

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4

CHAUBAN, Vishal, Sbivkanya FULORIA, Neeraj K. FULORIA, Syed R. HASHIM, and Sokindra KUMAR. "SYNTHESIS, CHARACTERIZATION AND COMPARATIVE SCREENING OF SOME NEWER 2-PHENYL INDOLE AND 5-CHLORO-2-PHENYL INDOLE DERIVATIVES." SOUTHERN BRAZILIAN JOURNAL OF CHEMISTRY 20, no. 20 (2012): 69–76. http://dx.doi.org/10.48141/sbjchem.v20.n20.2012.71_revista_2012a.pdf.

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Biologically active phenyl indole and chloro phenyl indole derivatives were efficiently synthesized. The reaction of 2-phenyl-1H-indole A and 5-chloro-2-phenyl-1H-indole B, with chloroacetylchloride yielded 2-chloro-1-(2-phenyl-1H-indol-1-yl)ethanone 1 and 2-chloro-1-(5-chloro-2-phenyl-1H-indol-1-yl)ethanone 4 respectively. Compound 1 and 4 on Friedal Crafts cyclization in presence of aluminium chloride and nitrobenzene yielded indolo[2,1 -alfa]isoquinolin-6(5H)-one 2 and 10-chloroindolo [2,1-alfa]isoquinolin-6(5H)-one 5 respectively, which upon hydrolysis afforded 2-(2-(1H-indol-2-yl)phenyl)a

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5

Aksenov, Alexander V., Nicolai A. Aksenov, Elena V. Aleksandrova, et al. "Direct Conversion of 3-(2-Nitroethyl)-1H-Indoles into 2-(1H-Indol-2-yl)Acetonitriles." Molecules 26, no. 20 (2021): 6132. http://dx.doi.org/10.3390/molecules26206132.

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The recently discovered [4+1]-spirocyclization of nitroalkenes to indoles provided a convenient new approach to 2-(1H-indol-2-yl)acetonitriles. However, this reaction was complicated by the formation of inert 3-(2-nitroethyl)-1H-indole byproducts. Herein, we offer a workaround this problem that allows for effective transformation of the unwanted byproducts into acetonitrile target molecules.

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6

Riar, G. K., D. Utreja, A. Kalia, and S. Kaur. "Synthesis and antipathogenic evaluation of isatin-indole Schiff bases as potent nematicidal and agrochemical agents." INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY 35, no. 02 (2025): 295. https://doi.org/10.59467/ijhc.2025.35.295.

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N-alkylated Schiff bases of isatin-indole were synthesized through the reaction of isatin hydrazide with indole-3-carbaldehyde followed by N-alkylation. The synthesized isatin-indole Schiff bases were evaluated for their in vitro antimicrobial activity against the pathogenic bacteria Dickeya sp. and Streptomyces sp., as well as the fungi Fusarium oxysporum and Rhizoctonia solani. In addition, their nematicidal potential was assessed against the tomato parasite Meloidogyne incognita through egg hatch inhibition and J2 mortality assays. The compounds were further evaluated for their inhibitory a

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7

Golantsov, Nikita, Alexey Festa, Alexey Varlamov, and Leonid Voskressensky. "Revision of the Structure and Total Synthesis of Topsentin C." Synthesis 49, no. 11 (2017): 2562–74. http://dx.doi.org/10.1055/s-0036-1588731.

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An efficient synthetic approach to access (indol-3-yl)ethane-1,2-diamines with a protecting group at the indole N atom from readily available 3-(2-nitrovinyl)indoles is reported. This approach includes solvent-free conjugate addition of O-pivaloylhydroxylamines to 1-Boc-3-(2-nitrovinyl)indoles followed by mild reduction of the adducts. The obtained (indol-3-yl)ethane-1,2-diamines are convenient synthetic precursors for several classes of marine alkaloids. The first total synthesis of racemic topsentin C, a secondary metabolite from Hexadella sp., based on this approach is reported. The initial

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8

Xu, Xiaobing, Jianchao Liu, Lin Lu, Furong Wang, and Biaolin Yin. "Pd-catalyzed regioselective intramolecular direct arylation of 3-indolecarboxamides: access to spiro-indoline-3,3′-oxindoles and 5,11-dihydro-6H-indolo[3,2-c]quinolin-6-ones." Chemical Communications 53, no. 55 (2017): 7796–99. http://dx.doi.org/10.1039/c7cc02256e.

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We report regioselective intramolecular direct C-3 and C-2 arylations of the indole rings of 3-indolecarboxamides for diastereospecific production of spiro-indoline-3,3′-oxindoles and 5,11-dihydro-6H-indolo[3,2-c]quinolin-6-ones, respectively, under different reaction conditions.

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9

Padmaja, Pannala, Pedavenkatagari Narayana Reddy, and Bijaya Ketan Sahoo. "A Green Approach to the Synthesis of Novel Indole Substituted 2-Amino- 4,5-dihydro-3-furancarbonitriles in Water." Letters in Organic Chemistry 16, no. 3 (2019): 209–14. http://dx.doi.org/10.2174/1570178615666180917104820.

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2-Amino-4,5-dihydro-3-furancarbonitriles (ADFCs) have attracted much attention due to their utility as valuable synthetic intermediates for the preparation of a series of acyclic and cyclic organic compounds. On the other hand, indoles substituted with furans are highly interesting compounds displaying a wide range of biological and pharmaceutical activities. However, to the best of our knowledge, indole substituted 2-amino-4,5-dihydro-3-furancarbonitriles have not been previously reported. A new and efficient synthesis of indole substituted 2-amino-4,5-dihydro-3-furancarbonitriles has been de

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10

Short, Spencer, Steven Rhodes, Vishakha S. Bhave, Ryoga Hojo, and Mukund Jha. "Metal-Free Hydroamination of Alkynes: A Mild and Concise Synthesis of Thiazolo[3,2-a]indoles and their Cytotoxic Activity." Synthesis 51, no. 22 (2019): 4263–70. http://dx.doi.org/10.1055/s-0039-1690680.

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A metal-free, mild and efficient method for the synthesis of thiazolo[3,2-a]indoles has been developed starting from indoline-2-thiones. The reaction methodology involves first the formation of thermally labile 2-(prop-2-ynylthio)-1H-indole intermediates, which undergo base-mediated intramolecular hydroamination to produce the title compounds in excellent yields.

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11

Kunevičius, Arnas, Mikas Sadauskas, Julija Raudytė, Rolandas Meškys, and Aurelijus Burokas. "Unraveling the Dynamics of Host–Microbiota Indole Metabolism: An Investigation of Indole, Indolin-2-one, Isatin, and 3-Hydroxyindolin-2-one." Molecules 29, no. 5 (2024): 993. http://dx.doi.org/10.3390/molecules29050993.

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The gut microbiota produces a variety of bioactive molecules that facilitate host–microbiota interaction. Indole and its metabolites are focused as possible biomarkers for various diseases. However, data on indole metabolism and individual metabolites remain limited. Hence, we investigated the metabolism and distribution of indole, indolin-2-one, isatin, and 3-hydroxyindolin-2-one. First, we orally administered a high dose of indole into C57BL/6J mice and measured the concentrations of indole metabolites in the brain, liver, plasma, large and small intestines, and cecum at multiple time points

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12

Kaur, Jaskirat, Divya Utreja, N. K. Dhillon, and Shivali Sharma. "Synthesis of Indole Derivatives and Their Evaluation against Root Knot Nematode Meloidogyne incognita." Letters in Organic Chemistry 16, no. 9 (2019): 759–67. http://dx.doi.org/10.2174/1570178616666190219131042.

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Eight new 2-(1H-indol-3-yl)-N-(aryl)-2-oxoacetamide amine based indole derivatives were synthesized. Microanalytical data, 1HNMR, 13CNMR, FT-IR and XRD were used to characterize the synthesized derivatives. The indole derivatives had also been screened for their nematicidal activity against root-knot nematode Meloidogyne incognita. Chlorine substituted indole derivatives had shown significant nematicidal activity comparative to other indole derivatives.

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13

Ametsetor, Ebenezer, Spencer Farthing, and Richard A. Bunce. "Domino Aza-Michael-SNAr-Heteroaromatization Route to C5-Substituted 1-Alkyl-1H-Indole-3-Carboxylic Esters." Molecules 27, no. 20 (2022): 6998. http://dx.doi.org/10.3390/molecules27206998.

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A new synthesis of C5-substituted 1-alkyl-1H-indole-3-carboxylic esters is reported. A series of methyl 2-arylacrylate aza-Michael acceptors were prepared with aromatic substitution to activate them towards SNAr reaction. Subsequent reaction with a series of primary amines generated the title compounds. Initially, the sequence was expected to produce indoline products, but oxidative heteroaromatization intervened to generate the indoles. The reaction proceeded under anhydrous conditions in DMF at 23–90 °C using equimolar quantities of the acrylate and the amine with 2 equiv. of K2CO3 to give 6

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14

Kerr, Jamie R., Laurent Trembleau, John M. D. Storey, James L. Wardell, and William T. A. Harrison. "Crystal structures of four indole derivatives with a phenyl substituent at the 2-position and a carbonyl group at the 3-position: theC(6) N—H...O chain remains the same, but the weak reinforcing interactions are different." Acta Crystallographica Section E Crystallographic Communications 72, no. 3 (2016): 363–69. http://dx.doi.org/10.1107/s2056989016002620.

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We describe the crystal structures of four indole derivatives with a phenyl ring at the 2-position and different carbonyl-linked substituents at the 3-position, namely 1-(2-phenyl-1H-indol-3-yl)ethanone, C16H13NO, (I), 2-cyclohexyl-1-(2-phenyl-1H-indol-3-yl)ethanone, C22H23NO, (II), 3,3-dimethyl-1-(2-phenyl-1H-indol-3-yl)butan-1-one, C20H21NO, (III), and 3-benzoyl-2-phenyl-1H-indole, C21H15NO, (IV). In each case, the carbonyl-group O atom lies close to the indole-ring plane and points towards the benzene ring. The dihedral angles between the indole ring system and 2-phenyl ring for these struc

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15

Kutschy, Peter, Mojmír Suchý, Milan Dzurilla, Mitsuo Takasugi, and Vladimír Kováčik. "A New Approach to Imidazo[1,5-a]indole Derivatives." Collection of Czechoslovak Chemical Communications 65, no. 7 (2000): 1163–72. http://dx.doi.org/10.1135/cccc20001163.

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Reaction of indole-2-carbonyl isothiocyanate (1) with sodium methanethiolate afforded 1-thioxo-1H-imidazo[1,5-a]indol-3(2H)-one (3). Its methylation with methyl iodide in the presence of lithium hydride in dimethylformamide, or potassium carbonate in acetone resulted in the formation of corresponding S- and N-methyl derivatives 4 and 5. N-(Indole-2-carbonyl)thiocarbamates and N-(indole-2-carbonyl)thioureas prepared by treatment of isothiocyanate 1 with corresponding nucleophilic reagents were S-methylated with methyl iodide in acetone in the presence of potassium carbonate. The obtained N-(ind

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16

Ashram, Muhammad, Ahmed Al-Mustafa, Wael A. Al-Zereini, Firas F. Awwadi, and Islam Ashram. "A convenient one-pot approach to the synthesis of novel pyrazino[1,2-a]indoles fused to heterocyclic systems and evaluation of their biological activity as acetylcholinesterase inhibitors." Zeitschrift für Naturforschung B 76, no. 5 (2021): 303–12. http://dx.doi.org/10.1515/znb-2020-0205.

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Abstract Pyrazino[1,2-a]indoles fused with various heterocycles, such as oxazolidine, oxazinane, imidazolidine, hexahydropyrimidine and benzimidazole, were synthesized transition metal-free by domino reactions which involved the condensation of 1-(2-bromoethyl)-3-chloro-1H-indole-2-carbaldehydes 28–31 with various nucleophilic amines, resulting in the formation of two new interesting fused heterocycles. The anticholinesterase, antioxidant and antibacterial activities of the compounds were evaluated. Acetylcholinesterase (AChE) inhibitory activities were tested by Ellman’s assay, antioxidant ac

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17

Dörnyei, Gábor, Mária Incze, Mária Kajtár-Peredy, and Csaba Szántay. "Intramolecular Mannich Reaction of 2-Oxotryptamine and Homologues with Oxo Reagents Yielding Spiro Compounds. Part II." Collection of Czechoslovak Chemical Communications 67, no. 11 (2002): 1669–80. http://dx.doi.org/10.1135/cccc20021669.

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2-Oxotryptamine and its homo derivative undergo intramolecular Mannich-type cyclization with acetone and other ketones to give spiro[indole-3,3'-pyrrolidin]-2-ones and spiro[indole-3,3'-piperidin]-2-ones. A similar reaction with the bis-homologue of 2-oxotryptamine to yield spiro[azepane-3,3'-indol]-2'-ones was unsuccessful.

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18

Morteza, Shiri, and Bozorgpour‑Savadjani Zahra. "Highly selective base-catalyzed ring closing Ugi-adducts from the reaction of 2-formylindole, 2-bromoacetic acid, amines and isocyanides." Journal of the Iranian Chemical Society 12, no. 3 (2014): 389–96. https://doi.org/10.1007/s13738-014-0495-6.

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The intermediate products of the Ugi reaction between indole-2-carboxaldehyde, 2bromoacetic acid, amines and isocyanides were treated with Cs2CO3 in DMF to form a series of novel cyclized 1,2-dihydropyrazino[1,2a]indol-3(4H)-ones (indole –NH cyclization) as major and piperazin-2-ones (amide –NH cyclization) as minor products.

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19

Karthikeyan, Iyyanar, Dhanarajan Arunprasath, and Govindasamy Sekar. "An efficient synthesis of pyrido[1,2-a]indoles through aza-Nazarov type cyclization." Chemical Communications 51, no. 9 (2015): 1701–4. http://dx.doi.org/10.1039/c4cc08783f.

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Transition metal free Brønsted acid mediated synthesis of pyrido[1,2-a]indole scaffolds has been developed through aza-Nazarov type cyclization of readily available diaryl(2-pyridyl)methanol using formic acid for the synthesis of biologically and medicinally important pyrido[1,2-a]indole, indolo[1,2-a]quinoline and pyrimido[1,2-a]indole derivatives.

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20

Dzurilla, Milan, Martin Ružinský, Peter Kutschy, Jalpa P. Tewari, and Vladimír Kováčik. "Application of 2-Substituted Ethyl Isothiocyanates and 2-Aminothiols in the Synthesis of the Analogs of Indole Phytoalexin Camalexin." Collection of Czechoslovak Chemical Communications 64, no. 9 (1999): 1448–56. http://dx.doi.org/10.1135/cccc19991448.

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Treatment of (indol-1-yl)magnesium bromide or iodide with 2-bromoethyl isothiocyanate afforded 1-(4,5-dihydrothiazol-2-yl)indole (6). Analogous reaction with 2,2-dimethoxyethyl isothiocyanate led to corresponding 1-thiocarbamoylindole derivative (7), which was cyclized to 1-(5-methoxy-4,5-dihydrothiazol-2-yl)indole (8) by treatment with boron trifluoride etherate. New analogs of camalexin, namely 4',5'-dihydrocamalexin (12) and benzocamalexin (14) were prepared by cyclocondensation reaction of 1-(tert-butoxycarbonyl)indole-3-carbaldehyde with cysteamine and 2-aminobenzenethiol. Antifungal acti

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21

Shakoori, Alireza, John B. Bremner, Mohammed K. Abdel-Hamid, Anthony C. Willis, Rachada Haritakun, and Paul A. Keller. "Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo." Beilstein Journal of Organic Chemistry 11 (April 15, 2015): 481–92. http://dx.doi.org/10.3762/bjoc.11.54.

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Diversity-directed synthesis based on the cascade allylation chemistry of indigo, with its embedded 2,2’-diindolic core, has resulted in rapid access to new examples of the hydroxy-8a,13-dihydroazepino[1,2-a:3,4-b']diindol-14(8H)-one skeleton in up to 51% yield. Additionally a derivative of the novel bridged heterocycle 7,8-dihydro-6H-6,8a-epoxyazepino[1,2-a:3,4-b']diindol-14(13H)-one was produced when the olefin of the allylic substrate was terminally disubstituted. Further optimisation also produced viable one-pot syntheses of derivatives of the spiro(indoline-2,9'-pyrido[1,2-a]indol)-3-one

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22

Kreher, Richard P., та Gerald Dyker. "Struktur und Reaktivität von isoanellierten heterocyclischen Systemen mit Anπ- und (4n+2)π-Elektronen, XII [1]. 2-tert-Butyl-4-methyl-2,4-dihydropyrrolo[3,4-b]indole: Tricyclische Hetarene mit isoanellierten Pyrrolringen / Structure and Reactivity of Isoannelated Heterocyclic Systems with 4nπ- and (4n+2)π-Electrons, XII [1] 2-terr-Butyl-4-methyl-2,4-dihydropyrrolo[3,4-b]indoles: Tricyclic Hetarenes with Isoannelated Pyrrole Rings". Zeitschrift für Naturforschung B 42, № 4 (1987): 473–77. http://dx.doi.org/10.1515/znb-1987-0414.

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2-tert-Butyl-4-methyl-2,4-dihydropyrrolo[3,4-b]indole (4a) has been prepared via selective reduction of 2-rm-butyl-4-methyl-2,4-dihydropyrrolo[3,4-b]indol-l(2H)-one or -3(2H)-one 5 and 6 with diisobutylaluminiumhydride. The same precursors 5 and 6 can be transformed into 2-tert-butyl-4-methyl-2,4-dihydropyrrolo[3,4-b]indoles (4b) and (4c) bearing a methoxy group in 1- or 3-position via a two step procedure consisting in O-alkylation and CH-deprotonation. NMR Investigations afford an insight into the structure of the stable tricyclic hetarenes.

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23

Nishio, Takehiko, Norikazu Okuda, and Choji Kashima. "Reduction of Indolin-2-ones and Desulfurization of Indoline-2-thiones to Indoline and Indole Derivatives." Helvetica Chimica Acta 73, no. 6 (1990): 1719–23. http://dx.doi.org/10.1002/hlca.19900730616.

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24

Boraei, Ahmed T. A., Ahmed A. M. Sarhan, Sammer Yousuf, and Assem Barakat. "Synthesis of a New Series of Nitrogen/Sulfur Heterocycles by Linking Four Rings: Indole; 1,2,4-Triazole; Pyridazine; and Quinoxaline." Molecules 25, no. 3 (2020): 450. http://dx.doi.org/10.3390/molecules25030450.

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A new series of nitrogen and sulfur heterocyclic systems were efficiently synthesized by linking the following four rings: indole; 1,2,4-triazole; pyridazine; and quinoxaline hybrids. The strength of the acid that catalyzes the condensation of 4-amino-5-(1H-indol-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 1 with aromatic aldehydes controlled the final product. Reflux in glacial acetic acid yielded Schiff bases 2–6, whereas concentrated HCl in ethanol resulted in a cyclization product at C-3 of the indole ring to create indolo-triazolo-pyridazinethiones 7–16. This fascinating cyclization appr

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25

Kerr, Jamie R., Laurent Trembleau, John M. D. Storey, James L. Wardell, and William T. A. Harrison. "Crystal structures of four indole derivatives as possible cannabinoid allosteric antagonists." Acta Crystallographica Section E Crystallographic Communications 71, no. 6 (2015): 654–59. http://dx.doi.org/10.1107/s2056989015008476.

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The crystal structures of four indole derivatives with various substituents at the 2-, 3- and 5-positions of the ring system are described, namely, ethyl 3-(5-chloro-2-phenyl-1H-indol-3-yl)-3-phenylpropanoate, C25H22ClNO2, (I), 2-bromo-3-(2-nitro-1-phenylethyl)-1H-indole, C16H13BrN2O2, (II), 5-methoxy-3-(2-nitro-1-phenylethyl)-2-phenyl-1H-indole, C23H20N2O3, (III), and 5-chloro-3-(2-nitro-1-phenylethyl)-2-phenyl-1H-indole, C22H17ClN2O2, (IV). The dominant intermolecular interaction in each case is an N—H...O hydrogen bond, which generates either chains or inversion dimers. Weak C—H...O, C—H...

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26

Clark, Christopher I., David P. Kelly, Roger F. Martin, Jonathan M. White, and Pavel Lobachevsky. "Synthesis and Binding Studies of a New DNA Minor Groove Binder." Australian Journal of Chemistry 51, no. 3 (1998): 243. http://dx.doi.org/10.1071/c97115.

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2-[2′-(4′′-Ethoxyphenyl)-1H-indol-6′-yl]-5-(4′′′-methylpiperazin-1′′′-yl)-1H-benzimidazole (1) has been synthesized from 2-(4′-ethoxyphenyl)-1H-indole-6-carbaldehyde (4b) and 4-(4′-methylpiperazin-1′-yl)benzene-1,2-diamine (3b). The aldehyde (4b) was prepared in five steps by using a modified Leimgruber–Batcho indole synthesis. Evaluation of (1) as a DNA ligand is described.

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27

Król, Marek, Grzegorz Ślifirski, Jerzy Kleps, et al. "The Synthesis and Absolute Configuration of Enantiomeric Pure (R)- and (S)-3-(piperidin-3-yl)-1H-Indole Derivatives." International Journal of Molecular Sciences 24, no. 1 (2022): 517. http://dx.doi.org/10.3390/ijms24010517.

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This article describes the synthesis of new chiral 3-(piperidin-3-yl)-1H-indole derivatives (R)-10a-c and (S)-11a-c from the corresponding diastereomers: (3R, 2R) and (3S, 2R)-2-[3-(1H-indol-3-yl)-1-piperidyl]-2-phenyl-acetamides (3R, 2R)-4a, (3R, 2R)-6b, (3R, 2R)-8c and (3S, 2R)-5a, (3S, 2R)-7b, (3S, 2R)-9c. Diastereomers were obtained by N-alkylation of derivatives of racemic 3-(piperidin-3-yl)-1H-indoles 1a-c using (S)-2-(4-toluenesulfonyloxy)-phenylacetic amide (S)–II. The same method was applied to obtain (3R, 2S)-methyl-2-[3-(1H-indole-3-yl)-1-piperidyl]-2-phenylacetate (3R, 2S)-2a and (

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28

Chakraborty, Amrita, Ankita, Nisha Kumari, and Ratnesh Kumar. "Synthesis of azepinoindolone derivative using Larock’s heteroannulation as key step." RESEARCH REVIEW International Journal of Multidisciplinary 8, no. 3 (2023): 52–64. http://dx.doi.org/10.31305/rrijm.2023.v08.n03.008.

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 Synthesis of tetrahydroazepino[4,5-b] indol-2(1H)-one derivative was achieved via intramolecular lactamization of the corresponding amine prepared from suitably designed 2,3-disubstituted indole. Larock’s heteroannulation was employed to get 2,3-disubstituted indole from tosyl protected 2-iodoaniline and internal alkyne which was prepared according to the methodology reported by Greg Fu.

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29

Katritzky, Alan R., Jianqing Li, and Christian V. Stevens. "Facile Synthesis of 2-Substituted Indoles and Indolo[3,2-b]carbazoles from 2-(Benzotriazol-1-ylmethyl)indole." Journal of Organic Chemistry 60, no. 11 (1995): 3401–4. http://dx.doi.org/10.1021/jo00116a026.

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30

Lajšic, Stevan, Gordana Cetkovic, Mirjana Popsavin, Velimir Popsavin, and Dušan Miljković. "Fischer Indole Synthesis with Selected 2,3-Dideoxy-D-glycero-aldopentose Derivatives. Conversion of D-Xylose to (2S)-3-(Indol-3-yl)propane-1,2-diol." Collection of Czechoslovak Chemical Communications 61, no. 2 (1996): 298–304. http://dx.doi.org/10.1135/cccc19960298.

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Two independent routes towards (2S)-3-(indol-3-yl)propane-1,2-diol (11) were achieved starting from 3,5-di-O-acetyl-1,2-O-cyclohexylidene-α-D-xylofuranose (1). Ethanethiolysis of 1 afforded acyclic diethyl dithioacetal 2 which was further O-deacetylated to give 3. Selective benzoylation of 3 gave 5-O-benzoyl derivative 4. Treatment of 4 with N-bromosuccinimide in methanol gave methyl furanoside 5 which was further desulfurized over Raney nickel to afford 6. An acid hydrolysis of 6 gave hemiacetal 7 which upon treatment with phenylhydrazine, according to standard Fischer indolization procedure,

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31

Aroca, P., F. Solano, J. C. Garcia-Borrón, and J. A. Lozano. "Specificity of dopachrome tautomerase and inhibition by carboxylated indoles. Considerations on the enzyme active site." Biochemical Journal 277, no. 2 (1991): 393–97. http://dx.doi.org/10.1042/bj2770393.

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Dopachrome tautomerase (EC 5.3.2.3) catalyses the tautomerization of dopachrome to 5,6-dihydroxyindole-2-carboxylic acid (DHICA) within the melanin-formation pathway. We have analysed a series of substrate analogues and related compounds as possible substrates and inhibitors of tautomerization. The enzyme appears to be highly specific since D-dopachrome, alpha-methyldopachrome, dopaminochrome, adrenochrome methyl ether and deoxyadrenochrome are not substrates. Conversely, dopachrome tautomerase catalyses the tautomerization of dopachrome methyl ester, suggesting that a carboxy group, either fr

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32

KRISHNA, C. JOSHI, N. PATHAK VIJAI, and CHAND POORAN. "Mass Spectral Studies on Heterocyclic Compounds. Part -I. Fragmentation of some Fluorine containing Indole Derivatives under Electron Impact." Journal of Indian Chemical Society Vol. 64, Feb 1987 (1987): 111–13. https://doi.org/10.5281/zenodo.6217752.

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Department of Chemistry, University of Rajasthan, Jaipur-302 004 <em>Manuscript received 21 August 1980, accepted 22 January 1987</em> The fragmentation pathways of 5-)6-fluoro-2-(4'-fluorophenyl)indoles, 5-fluoro-2- (4' -fluorophenyI)-3- <em>(N,N-</em>dimethy Iglyoxy lamido)indol e, 5-fluoro -2- (4'-fluorophenyl)-3-(β- morpholinoethyl) indole and 5-fluoro-3-(4'-fluorophenylimino)-1-piperidino-methylindo1-2- one have been studied. Structural assignments have been made for the major fragments, and the pathways leading to their formation have been postulated by the recogniti

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33

Chen, Xiao Yun, Yaonan Tang, Xinran Xiang, et al. "Green One-Pot Syntheses of 2-Sulfoximidoyl-3,6-Dibromo Indoles Using N-Br Sulfoximines as Both Brominating and Sulfoximinating Reagents." Molecules 28, no. 8 (2023): 3380. http://dx.doi.org/10.3390/molecules28083380.

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A green one-pot 2,3,6-trifunctionalization of N-alkyl/aryl indoles was achieved by adding three equivalents of N-Br sulfoximine to the indole solution. A variety of 2-sulfoximidoyl-3,6-dibromo indoles were prepared with 38–94% yields using N-Br sulfoximines as both brominating and sulfoximinating reagents. Based on the results of controlled experiments, we propose that a radical substitution involving 3,6-dibromination and 2-sulfoximination occurs in the reaction process. This is first time that 2,3,6-trifunctionalization of indole in one pot has been achieved.

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34

Zeng, Ming, Jiaqi Chen, Fengye Li, et al. "Ruthenium-Catalyzed Oxidative Synthesis of N-(2-triazine)indoles by C-H Activation." Molecules 28, no. 9 (2023): 3676. http://dx.doi.org/10.3390/molecules28093676.

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1,3,5 triazines, especially indole functionalized triazine derivatives, exhibit excellent activities, such as anti-tumor, antibacterial, and anti-inflammatory activities. Traditional methods for the synthesis of N-(2-triazine) indoles suffer from unstable materials and tedious operations. Transition-metal-catalyzed C-C/C-N coupling provides a powerful protocol for the synthesis of indoles by the C-H activation strategy. Here, we report the efficient ruthenium-catalyzed oxidative synthesis of N-(2-triazine) indoles by C-H activation from alkynes and various substituted triazine derivatives in a

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35

Connon, Robert, Laura Carroll, and Patrick J. Guiry. "A Base-Promoted One-Pot Asymmetric Friedel–Crafts Alkylation/Michael Addition of 4-Substituted Indoles." Synthesis 52, no. 08 (2019): 1215–22. http://dx.doi.org/10.1055/s-0039-1690241.

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Herein, we report a base-promoted Zn(II)–bis(oxazoline)-catalyzed one-pot Friedel–Crafts alkylation/Michael addition of 3-(indol-4-yl)acrylonitrile derivatives with trans-β-nitrostyrenes to yield the tricyclic core of the ergoline skeleton in up to 71% yield and 85% ee. During the purification of 3-(indol-4-yl)acrylonitrile, the key substrate for catalytic studies, a novel trans-cis-trans-cyclobutane derivative, thought to be formed via a [2+2] light-promoted cycloaddition, was identified by X-ray crystallographic analysis. Finally, a novel class of 4-substituted bis(indole)methane derivatives

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36

Padrtová, Tereza, Pavlína Marvanová, Renáta Kubínová, et al. "Indol-2-Carboxylic Acid Esters Containing N-Phenylpiperazine Moiety - Preparation and Cholinesterase-inhibiting Activity." Current Organic Synthesis 17, no. 7 (2020): 576–87. http://dx.doi.org/10.2174/1570179417666200619132218.

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Background: The indole derivatives and the N-phenylpiperazine fragment represent interesting molecular moieties suitable for the research of new potentially biologically active compounds. This study was undertaken to identify if indol-2-carboxylic acid esters containing N-phenylpiperazine moiety possess acetylcholinesterase and butyrylcholinesterase inhibitory activity. Materials and Methods: The study dealt with the synthesis of a novel series of analogs of 1H-indole-2- carboxylic acid and 3-methyl-1H-indole-2-carboxylic acid. The structure of the derivatives was represented by the indolylcar

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37

Rahman, Md Lutfor, Ajaykumar D. Kulkarni, Mashitah Mohd. Yusoff, Huey Chong Kwong, and Ching Kheng Quah. "Crystal structure of 3-{5-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-1H-pyrazol-1-yl}indolin-2-one ethanol monosolvate." Acta Crystallographica Section E Crystallographic Communications 72, no. 3 (2016): 283–86. http://dx.doi.org/10.1107/s2056989016001614.

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The title indolin-2-one compound, C28H23FN4O·C2H6O, crystallizes as a 1:1 ethanol solvate. The ethanol molecule is disordered over two positions with refined site occupancies of 0.560 (14) and 0.440 (14). The pyrazole ring makes dihedral angles of 84.16 (10) and 85.33 (9)° with the indolin-2-one and indole rings, respectively, whereas the dihedral angle between indolin-2-one and indole rings is 57.30 (7)°. In the crystal, the components are linked by N—H...O and O—H...O hydrogen bonds, forming an inversion molecule–solvate 2:2 dimer withR44(12) ring motifs. The crystal structure is consolidate

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38

Mao, Peng-Fei, Li-Jin Zhou, An-Qi Zheng, Chun-Bao Miao, and Hai-Tao Yang. "Cu(OAc)2-Triggered Cascade Reaction of Malonate-Tethered Acyl Oximes with Indoles, Indole-2-alcohols, and Indole-2-carboxamides." Organic Letters 21, no. 9 (2019): 3153–57. http://dx.doi.org/10.1021/acs.orglett.9b00849.

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39

El-Sawy, Eslam, Fatma Bassyouni, Sherifa Abu-Bakr, Hanaa Rady, and Mohamed Abdlla. "Synthesis and biological activity of some new 1-benzyl and 1-benzoyl-3-heterocyclic indole derivatives." Acta Pharmaceutica 60, no. 1 (2010): 55–71. http://dx.doi.org/10.2478/v10007-010-0004-0.

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Synthesis and biological activity of some new 1-benzyl and 1-benzoyl-3-heterocyclic indole derivativesStarting from 1-benzyl- (2a) and 1-benzoyl-3-bromoacetyl indoles (2b) new heterocyclic, 2-thioxoimidazolidine (4a, b), imidazolidine-2,4-dione (5a, b), pyrano(2,3-d)imida-zole (8a, band9a, b), 2-substituted quinoxaline (11a, b-17a, b) and triazolo(4,3-a)quinoxaline derivatives (18a, band19a, b) were synthesized and evaluated for their antimicrobial and anticancer activities. Antimicrobial activity screening performed with concentrations of 0.88, 0.44 and 0.22 μg mm-2showed that 3-(1-substitute

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40

Uruvakili, Anasuyamma, and K. C. Kumara Swamy. "Gold catalysed transformation of 2-arylindoles to terphenyl amines via 3-dienyl indoles and Brønsted acid promoted formation of 2-carboxyindoles to 3-indenylindoles via 3-allenylindoles." Organic & Biomolecular Chemistry 17, no. 12 (2019): 3275–84. http://dx.doi.org/10.1039/c9ob00232d.

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41

Carvalho, Paulo, Edward B. Furr III, and Christopher McCurdy. "(E)-Methyl 2-[(2S,3S,12bR)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyacrylate ethanol solvate." Acta Crystallographica Section E Structure Reports Online 65, no. 6 (2009): o1441—o1442. http://dx.doi.org/10.1107/s1600536809017309.

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In the title compound, C23H30N2O4·C2H6O, the indole derivative has four fused rings, forming an indolo[2-3a]quinolizine system, in which one six-membered ring is directly connected to the indole unit and has a distorted chair conformation. The fourth ring is also a six-membered ring, depicting a regular chair conformation. In the crystal, the molecules are linked by N—H...O and O—H...N interactions, forming aC(7) chain.

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42

Kadam, Hari K., and Santosh G. Tilve. "6H-Indolo[2,3-b]Quinoline: A Recent Synthetic Comprehension." Mini-Reviews in Organic Chemistry 16, no. 1 (2018): 35–42. http://dx.doi.org/10.2174/1570193x15666180528103548.

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The present review provides a comprehensive overview of the synthetic methods developed recently for 6H-Indolo[2,3-b]quinoline. The review is classified into the following: 1) inheriting indole skeleton and constructing quinoline ring; 2) inheriting quinoline skeleton and constructing indole ring, and 3) convergent strategies constructing both rings simultaneously or step by step. This review discusses the scope of multifunctional reactivity of indole and quinoline skeleton for constructing the desired indoloquinolines as explored in various research strategies.

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43

Salama, Eid E., Saad Alrashdi, Ahmed T. A. Boraei, et al. "Utilizing Some Indole Derivatives to Control Mild Steel Corrosion in Acidic Environments: Electrochemical and Theoretical Methods." Molecules 30, no. 6 (2025): 1235. https://doi.org/10.3390/molecules30061235.

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Ethyl 3-formyl-1H-indol-2-carboxylate (FIC) and 2-(4-methoxyphenyl)-2,4-dihydropyrrolo [3,4-b]indol-3-ol (MPI) were synthesized as indole derivatives. The chemical structures of FIC and MPI were established through analytical and spectroscopic techniques. The inhibitory impacts of FIC and MPI on mild steel (MS) in an acidic environment (0.5 M H2SO4) were investigated by employing methodologies including open circuit potential (OCP), electrochemical impedance spectroscopy (EIS), and potentiodynamic polarization (PDP). As the studied indole derivatives adsorbed on the surface of MS, they created

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44

Ryabova, Svetlana Yu, Nina A. Rastorgueva, Eduard J. Sonneveld, et al. "Structural characterization of [1,4]diazepino[6,5-b]indoles by powder diffraction." Acta Crystallographica Section B Structural Science 61, no. 2 (2005): 192–99. http://dx.doi.org/10.1107/s0108768105006075.

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As part of a systematic structural study of potentially pharmacologically active [1,4]diazepino[6,5-b]indoles, the crystal structures of nine compounds have been determined from laboratory powder diffraction data. The investigated compounds are: 2-oxo-1-(4-nitrophenyl)-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole-4-oxide, C17H12N4O4 (1a); 2-oxo-1-phenyl-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole-4-oxide, C17H13N3O2 (1b); 2-oxo-1-(4-ethoxyphenyl)-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole-4-oxide, C19H17N3O3 (1c); 2-oxo-1-(4-chlorophenyl)-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole-4-o

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45

Macha, Lingamurthy, Deepak Singh, Hyong-Jin Rhee, and Hyun-Joon Ha. "Lewis acid-mediated synthesis of mono- and tris-indole adducts from chiral aziridines." Organic & Biomolecular Chemistry 18, no. 46 (2020): 9473–82. http://dx.doi.org/10.1039/d0ob01865a.

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46

Liu, Xiang-Hong, Feng-Ping Miao, Xiao-Dong Li, Xiu-Li Yin, and Nai-Yun Ji. "A New Sesquiterpene from an Endophytic Aspergillus versicolor Strain." Natural Product Communications 7, no. 7 (2012): 1934578X1200700. http://dx.doi.org/10.1177/1934578x1200700702.

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A new sesquiterpene, albican-11,14-diol (1), and seven known compounds, including sterigmatocystin (2), 3-hydroxy-5-(hydroxymethyl)-4-(4′-hydroxyphenoxy) pyrrolidin-2-one (3), (1 H-indol-3-yl) oxoacetamide (4), indole-3-carboxylic acid (5), indole-3-acetic acid (6), indole-3-carboxaldehyde (7), and volemolide (8), were isolated from the cultures of Aspergillus versicolor, an endophytic fungus isolated from the marine green alga Codium fragile. The structure of 1 was elucidated by 1D, 2D NMR and mass spectroscopic techniques. The bioassay results showed that 1 possessed potent activity against

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47

Mir, Abid Ali, and Vinata V. Mulwad. "Synthesis and anti-bacterial screening of ethyl 6-oxo-3-phenyl-1,6-dihydropyrano[3,2-e]indole-2-carboxylate and 7-phenyl-5H-pyrano [3′,2′:4,5]indolo[1,2-a]quinoxaline-6,10-dione." Journal of Chemical Research 2009, no. 5 (2009): 290–92. http://dx.doi.org/10.3184/030823409x447691.

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Ethyl 6-oxo-3-phenyl-1,6-dihydropyrano[3,2- e]indole-2-carboxylate 3a-c were synthesised from ethyl 2-[(2-oxo-2 H-1-benzopyran-6-yl)-hydrazono]-3-phenylpropanoate 2a-c. Compounds 2a-c was in turn prepared by reacting diasotised solution of 6-aminocoumarin and ethyl-2-benzylacetoacetate. N-nitroarylation of ethyl 6-oxo-3-phenyl-1,6-dihydropyrano[3,2- e]indole-2-carboxylate 3a-c was carried out with 2-chloronitrobenzene to give ethyl 1-(2-nitrophenyl)-6-oxo-3-phenyl-1,6-dihydropyrano[3,2- e]indole-2-carboxylate 4a-c, which on catalytic reductive cyclisation with H2/Ni affords 7-phenyl-5 H-pyrano

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48

Liu, Yun-Lin, Xiang-Yu Mao, Xiao-Tong Lin, and Guo-Shu Chen. "A Zn(OTf)2 catalyzed Ugi-type reaction of 3-(2-isocyanoethyl)indoles with indole-derived ketimines: rapid access to hexacyclic spiroindolines." Organic Chemistry Frontiers 5, no. 15 (2018): 2303–7. http://dx.doi.org/10.1039/c8qo00382c.

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A Zn(OTf)<sub>2</sub> catalyzed Ugi-type reaction of 3-(2-isocyanoethyl)indoles and indole-derived ketimines was developed for the synthesis of hexacyclic spiroindolines featuring three stereocenters including two quaternary stereocenters.

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Ye, Zhi-Shi, Jin-Chen Li, and Gang Wang. "Transition-Metal-Catalyzed Enantioselective Synthesis of Indoles from 2-Alkynylanilines." Synthesis 54, no. 09 (2022): 2133–47. http://dx.doi.org/10.1055/a-1729-9572.

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AbstractOptically active indole derivatives are ubiquitous in natural products and are widely recognized as privileged components in pharmacologically relevant compounds. Therefore, developing catalytic asymmetric approaches for constructing indole derivatives is highly desirable. In this short review, we summarize methods for the transition-metal-catalyzed enantioselective synthesis of indoles from 2-alkynylanilines.1 Introduction2 Aminometalation-Triggered Asymmetric Cross-Coupling Reactions/Insertion2.1 Asymmetric Cross-Coupling Reactions2.2 Asymmetric Insertion of C=O, C=C and C≡N Bonds3

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S., Guru, Yadav R., Srivastava Soumya, K. Srivastava S., and D. Srivastava S. "Synthesis of some new N1-[(2-oxo-3-chloro-4-aryl-azitidin)-(acetyl amino)]-indole derivatives and their pharmacological activity." Journal of Indian Chemical Society Vol. 83, Dec 2006 (2006): 1236–124. https://doi.org/10.5281/zenodo.5834026.

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Synthetic Organic Chemistry Laboratory, Department of Chemistry, Dr. H. S. Gour University, Sagar-470 003, Madhya Pradesh, India <em>E-mail </em>: professorsks@rediffmail.com <em>Manuscript received 17 March 2006, revised 25 July 2006, accepted 7 September 2006</em> Indole on reaction with chloroacetyl chloride afforded N<sup>1</sup>-(1-chloro acetyl)-indole which was renuxed with hydrazine hydrate to give <em>N</em><sup>1</sup>-[(1-hydrazino)acetyl]-indole. The hydrazino derivative of indole was further treated with various substituted aromatic carbonyls to get <em>N</em><sup>1</sup>-[(benzyl

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