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References (45)
-
Ioannis Kostas, C. Screttas (1997)
Synthesis and Applications of Tetrahydrofuran-Stable Substituted (3-Lithioxyalkyl)- and (4-Lithioxyalkyl)lithiums, Modified with Magnesium 2-EthoxyethoxideJournal of Organic Chemistry, 62
-
R. Vicente (2011)
Recent advances in indole syntheses: new routes for a classic target.Organic & biomolecular chemistry, 9 19
-
A. Stein, F. Bilheri, G. Zeni (2015)
Application of organoselenides in the Suzuki, Negishi, Sonogashira and Kumada cross-coupling reactions.Chemical communications, 51 85
-
L. Ackermann (2005)
General and efficient indole syntheses based on catalytic amination reactions.Organic letters, 7 3
-
Nirmalya Mukherjee, D. Kundu, B. Ranu (2017)
Copper‐Silver Dual Catalyzed Decyanative C–Se Cross‐CouplingAdvanced Synthesis & Catalysis, 359
-
S. Shefali, S. Srivastava, S. Husbands, J. Lewis (2005)
Extension of the Nenitzescu reaction to simple ketones provides an efficient route to 1'-alkyl-5'-hydroxynaltrindole analogues, potent and selective delta-opioid receptor antagonists.Journal of medicinal chemistry, 48 2
-
M. Shen, Guisheng Li, B. Lu, Azad Hossain, F. Roschangar, V. Farina, C. Senanayake (2004)
The first regioselective palladium-catalyzed indolization of 2-bromo- or 2-chloroanilines with internal alkynes: a new approach to 2,3-disubstituted indoles.Organic letters, 6 22
-
C. Radatz, Diego Alves, P. Schneider (2013)
Direct synthesis of 2-aryl-1,3-benzoselenazoles by reaction of bis(2-aminophenyl) diselenides with aryl aldehydes using sodium metabisulfiteTetrahedron, 69
-
Daniel Rampon, L. Wessjohann, P. Schneider (2013)
Palladium-catalyzed direct arylation of selenophene.The Journal of organic chemistry, 79 13
-
F. Settimo, F. Simorini, S. Taliani, C. Motta, A. Marini, S. Salerno, M. Bellandi, E. Novellino, G. Greco, B. Cosimelli, E. Pozzo, B. Costa, N. Simola, M. Morelli, C. Martini (2008)
Anxiolytic-like effects of N,N-dialkyl-2-phenylindol-3-ylglyoxylamides by modulation of translocator protein promoting neurosteroid biosynthesis.Journal of medicinal chemistry, 51 18
-
A. Rodriguez, Christopher Koradin, W. Dohle, P. Knochel (2000)
Versatile Indole Synthesis by a 5-endo-dig Cyclization Mediated by Potassium or Cesium Bases.ChemInform, 31
-
F. Manarin, J. Roehrs, R. Gay, R. Brandão, P. Menezes, C. Nogueira, G. Zeni (2009)
Electrophilic cyclization of 2-chalcogenealkynylanisoles: versatile access to 2-chalcogen-benzo[b]furans.The Journal of organic chemistry, 74 5
-
Douglas Horton, G. Bourne, M. Smythe (2003)
The combinatorial synthesis of bicyclic privileged structures or privileged substructures.Chemical reviews, 103 3
-
Dong‐Fen Luo, Ge Wu, Hang Yang, Miao-chang Liu, Wenxia Gao, Xiaobo Huang, Jiuxi Chen, Hua-yue Wu (2016)
Copper-Catalyzed Three-Component Reaction for Regioselective Aryl- and Heteroarylselenation of Indoles using Selenium Powder.The Journal of organic chemistry, 81 11
-
C. Radatz, Daniel Rampon, Renata Balaguez, Diego Alves, P. Schneider (2014)
Synthesis of 2‐Substituted 1,3‐Benzoselenazoles from Carboxylic Acids Promoted by TributylphosphineEuropean Journal of Organic Chemistry, 2014
-
F. Weinhold, C. Landis (2001)
NATURAL BOND ORBITALS AND EXTENSIONS OF LOCALIZED BONDING CONCEPTSChemistry Education Research and Practice, 2
-
W. Lim, Y. Rhee (2013)
A Flexible Metal‐Catalyzed Synthesis of Highly Substituted Aryl Phenanthrenyl SelenidesEuropean Journal of Organic Chemistry, 2013
-
I. Choi, Hyunho Chung, Jang Park, Y. Chung (2016)
Active and Recyclable Catalytic Synthesis of Indoles by Reductive Cyclization of 2-(2-Nitroaryl)acetonitriles in the Presence of Co-Rh Heterobimetallic Nanoparticles with Atmospheric Hydrogen under Mild Conditions.Organic letters, 18 21
-
Tiago Frizon, Daniel Rampon, H. Gallardo, A. Merlo, P. Schneider, O. Rodrigues, A. Braga (2012)
Selenides and diselenides containing oxadiazoles: a new class of functionalised materialsLiquid Crystals, 39
-
M. Tiecco, L. Testaferri, A. Temperini, L. Bagnoli, F. Marini, C. Santi, Raffaella Terlizzi (2004)
Synthesis of Substituted Se‐Phenyl Selenocarboxylates from Terminal AlkynesEuropean Journal of Organic Chemistry, 2004
-
D.‐Y. Yang, Xian Huang* (1997)
Stereoselective synthesis of conjugated alkadienes via the palladium-catalyzed coupling reaction of (Z)- or (E)-alkenylboranes with (Z)- or (E)-2-halo-1-(alkylseleno)ethenesJournal of Organometallic Chemistry, 543
-
Norio Sakai, Kimiyoshi Annaka, T. Konakahara (2004)
Palladium-catalyzed coupling reaction of terminal alkynes with aryl iodides in the presence of indium tribromide and its application to a one-pot synthesis of 2-phenylindole.Organic letters, 6 10
-
M. Al-Hassan (2001)
HYDROALUMINATION AND BROMINATION OF 1-(PHENYL-SELENYL)-1-ALKYNESSynthetic Communications, 31
-
Adriane Sperança, Benhur Godoi, P. Menezes, G. Zeni (2013)
Application of FeCl3/Diorganyl Diselenides to Cyclization of o-Alkynyl Anilines: Synthesis of 3-Organoselenyl-(N-methyl)indolesSynlett, 24
-
Everton Zimmermann, S. Thurow, Camilo Freitas, Samuel Mendes, G. Perin, Diego Alves, R. Jacob, E. Lenardão (2013)
A Selenium-Based Ionic Liquid as a Recyclable Solvent for the Catalyst-Free Synthesis of 3-SelenylindolesMolecules, 18
-
G. Zeni, C. Nogueira, Jesus Pena, C. Pilissão, P. Menezes, A. Braga, J. Rocha (2003)
Stereospecific Synthesis of Chalcogenoenynes by Palladium-Catalyzed Cross-Coupling ReactionSynlett, 2003
-
C. Breneman, K. Wiberg (1990)
Determining atom‐centered monopoles from molecular electrostatic potentials. The need for high sampling density in formamide conformational analysisJournal of Computational Chemistry, 11
-
J. Azeredo, M. Godoi, Guilherme Martins, C. Silveira, A. Braga (2014)
A solvent- and metal-free synthesis of 3-chacogenyl-indoles employing DMSO/I2 as an eco-friendly catalytic oxidation system.The Journal of organic chemistry, 79 9
-
Alain Rodriguez, Christopher Koradin, W. Dohle, P. Knochel (2000)
Vielseitige Indolsynthese durch eine Kalium‐ oder Caesiumbasen‐vermittelte 5‐endo‐dig‐CyclisierungAngewandte Chemie, 112
-
G. Humphrey, J. Kuethe (2006)
Practical methodologies for the synthesis of indoles.Chemical reviews, 106 7
-
C. Silveira, A. Braga, A. Vieira, G. Zeni (2003)
Stereoselective synthesis of enynes by nickel-catalyzed cross-coupling of divinylic chalcogenides with alkynes.The Journal of organic chemistry, 68 2
-
Daniel Rampon, F. Rodembusch, P. Gonçalves, R. Lourega, A. Merlo, P. Schneider (2010)
An evaluation of the chalcogen atom effect on the mesomorphic and electronic properties in a new homologous series of chalcogeno estersJournal of the Brazilian Chemical Society, 21
-
J. Tomasi, B. Mennucci, R. Cammi (2005)
Quantum mechanical continuum solvation models.Chemical reviews, 105 8
-
A. Krief, J. Bousbaa (1997)
ω-Alkenyl-α-Methoxy-Benzyllithiums : Original Synthesis and ReactivityTetrahedron Letters, 38
-
M. Sevrin, D. Ende, A. Krief (1976)
Reduction or alkylative reduction of the carbonyl groupTetrahedron Letters, 17
-
A. Arcadi, S. Cacchi*, G. Fabrizi, F. Marinelli, Luca Parisi (2005)
Palladium-catalyzed reaction of o-alkynyltrifluoroacetanilides with 1-bromoalkynes. An approach to 2-substituted 3-alkynylindoles and 2-substituted 3-acylindoles.The Journal of organic chemistry, 70 16
-
Nicholas McGrath, Matthew Brichacek, J. Njardarson (2010)
A Graphical Journey of Innovative Organic Architectures That Have Improved Our LivesJournal of Chemical Education, 87
-
A. Arcadi, E. Pietropaolo, A. Alvino, V. Michelet (2013)
One-pot gold-catalyzed aminofluorination of unprotected 2-alkynylanilines.Organic letters, 15 11
-
Xiaodan Zhao, Zhengkun Yu, Tongyu Xu, Ping Wu, Hai-feng Yu (2007)
Novel Brønsted acid catalyzed three-component alkylations of indoles with N-phenylselenophthalimide and styrenes.Organic letters, 9 25
-
Jin-Hyung Lee, T. Wood, Jintae Lee (2015)
Roles of indole as an interspecies and interkingdom signaling molecule.Trends in microbiology, 23 11
-
Bart Esseveldt, F. Delft, J. Smits, R. Gelder, H. Schoemaker, F. Rutjes (2004)
Transition metal-catalyzed synthesis of novel biologically relevant tryptophan analoguesAdvanced Synthesis & Catalysis, 346
-
G. Gribble (2010)
Recent developments in indole ring synthesis—methodology and applicationsContemporary Organic Synthesis, 1
-
Takeshi Yanai, D. Tew, N. Handy (2004)
A new hybrid exchange–correlation functional using the Coulomb-attenuating method (CAM-B3LYP)Chemical Physics Letters, 393
-
A. Martynov, V. Potapov, S. Amosova, N. Makhaeva, I. Beletskaya, L. Hevesi (2003)
Cross-coupling of (Z)-1,2-bis(ethylseleno)ethene with the Grignard reagentsJournal of Organometallic Chemistry, 674
-
J. Comasseto, P. Menezes, H. Stefani, G. Zeni, A. Braga (1996)
ADDITION OF HYDROGEN HALIDES TO ACETYLENIC SELENIDES. SYNTHESIS OF 1-HALO-1-SELENOALKENESTetrahedron, 52
- Publisher
- Wiley
- Copyright
- © 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
- ISSN
- 0947-6539
- eISSN
- 1521-3765
- DOI
- 10.1002/chem.201901667
- Publisher site
- See Article on Publisher Site
Abstract
In this work, a series of 2‐chalcogenylindoles was synthesized by an efficient methodology, starting from chalcogenoalkynes, including a previously unreported tellurium indole derivative. For the first time, these 2‐substituted chalcogenylindoles were obtained in the absence of metal catalyst or base, under thermal conditions only. In addition, the results described herein represent a methodology with inverse regioselectivity for the chalcogen functionalization of indoles.
Journal
Chemistry - A European Journal – Wiley
Published: Jun 18, 2020
Keywords: ; ; ; ;