Synthesis and Characterization of 2‐(2‐Pyridinyl)pyrazine and 2,2′‐Bipyrazine Derivatives

KomReddy, Venugopal; Rillema, D. Paul; Nguyen, Huy; Kadel, Lava

doi:10.1002/jhet.3479

Title: Synthesis and Characterization of 2‐(2‐Pyridinyl)pyrazine and 2,2′‐Bipyrazine Derivatives

Journal Article · 28 January 2019 · Journal of Heterocyclic Chemistry

DOI: https://doi.org/10.1002/jhet.3479 · OSTI ID:1492900

KomReddy, Venugopal ^[1];

^[1]; Nguyen, Huy ^[1]; Kadel, Lava ^[1]

Department of Chemistry Wichita State University Wichita Kansas 67260 USA

A convenient and high yield preparation of derivatives of 2‐(2‐pyridinyl)pyrazine and derivatives of 2,2′‐bipyrazine compounds from their derivatives of bromopyrazine using Stille coupling is reported. X‐ray structures, elemental analyses, ¹ H, ¹³ C‐NMR, and mass spectral data of the compounds are given.

View Accepted Manuscript (Publisher)

Cite

Export

Save

Sponsoring Organization:: USDOE

OSTI ID:: 1492900

Journal Information:: Journal of Heterocyclic Chemistry, Journal Name: Journal of Heterocyclic Chemistry Journal Issue: 3 Vol. 56; ISSN 0022-152X

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: United States

Language:: English

References (35)

Silyl-Mediated Halogen/Halogen Displacement in Pyridines and Other Heterocycles Schlosser, Manfred; Cottet, Fabrice European Journal of Organic Chemistry, Vol. 2002, Issue 24 https://doi.org/10.1002/1099-0690(200212)2002:24<4181::AID-EJOC4181>3.0.CO;2-M	journal	December 2002
The Palladium-Catalyzed Cross-Coupling Reactions of Organotin Reagents with Organic Electrophiles [New Synthetic Methods(58)] Stille, John K. Angewandte Chemie International Edition in English, Vol. 25, Issue 6, p. 508-524 https://doi.org/10.1002/anie.198605081	journal	June 1986
Ueber die Ersetzung der Amidgruppe durch Chlor in den aromatischen Substanzen Sandmeyer, Traugott Berichte der deutschen chemischen Gesellschaft, Vol. 17, Issue 2 https://doi.org/10.1002/cber.18840170219	journal	July 1884
Aryl-aryl bonds formation in pyridine and diazine series. Diazines part 41 Boully, Ludovic; Turck, Alain; Plé, Nelly Journal of Heterocyclic Chemistry, Vol. 42, Issue 7 https://doi.org/10.1002/jhet.5570420726	journal	November 2005
Strategies for the synthesis of unsymmetrical quaterpyridines using palladium-catalyzed cross-coupling reactions A. Zolewicz, John; P. Cruskie, Michael Tetrahedron, Vol. 51, Issue 42 https://doi.org/10.1016/0040-4020(95)00699-9	journal	October 1995
Synthesis and crystal structure of the low-spin iron(II) complex [Fe(bpz)3](ClO4)2·H2O (bpz=2,2′-bipyrazine) Marilena Toma, Luminita; Eller, Chad; Paul Rillema, D. Inorganica Chimica Acta, Vol. 357, Issue 9 https://doi.org/10.1016/j.ica.2003.12.046	journal	July 2004
Palladium-Catalyzed Modular Synthesis of Substituted Piperazines and Related Nitrogen Heterocycles Montgomery, Thomas D.; Rawal, Viresh H. Organic Letters, Vol. 18, Issue 4 https://doi.org/10.1021/acs.orglett.5b03708	journal	January 2016
Synthesis and Characterization of a Novel Vinyl-2,2′-bipyridine Monomer and Its Homopolymeric/Copolymeric Metal Complexes Pefkianakis, Elefterios K.; Tzanetos, Nikolaos P.; Kallitsis, Joannis K. Chemistry of Materials, Vol. 20, Issue 19 https://doi.org/10.1021/cm800911y	journal	October 2008
Computational and Spectroscopic Studies of Re(I) Bipyridyl Complexes Containing 2,6-Dimethylphenylisocyanide (CNx) Ligand Stoyanov, Stanislav R.; Villegas, John M.; Cruz, Arvin J. Journal of Chemical Theory and Computation, Vol. 1, Issue 1 https://doi.org/10.1021/ct049956g	journal	October 2004
Photophysical properties of rhenium(I) tricarbonyl complexes containing alkyl- and aryl-substituted phenanthrolines as ligands Wallace, Lynne; Rillema, D. Paul Inorganic Chemistry, Vol. 32, Issue 18 https://doi.org/10.1021/ic00070a012	journal	September 1993
Complexes of ruthenium(II) with (2,2'-bipyrimidine)tricarbonylchlororhenium and {benzo[1,2-6:3,4-b':5,6-b"]tripyrazine}hexacarbonyldichloridirhenium as ligands: syntheses and redox and luminescence properties Sahai, Ram; Rillema, D. Paul; Shaver, Randy Inorganic Chemistry, Vol. 28, Issue 6 https://doi.org/10.1021/ic00305a008	journal	March 1989
Solar Energy Conversion by Dye-Sensitized Photovoltaic Cells Grätzel, Michael Inorganic Chemistry, Vol. 44, Issue 20 https://doi.org/10.1021/ic0508371	journal	October 2005
Synthesis, Characterization, Photophysical, and Computational Studies of Rhenium(I) Tricarbonyl Complexes Containing the Derivatives of Bipyrazine Kirgan, Robert; Simpson, Megan; Moore, Curtis Inorganic Chemistry, Vol. 46, Issue 16 https://doi.org/10.1021/ic700512j	journal	August 2007
2-Bromopyrazines, 2-Cyanopyrazines and their Derivatives Karmas, George; Spoerri, Paul E. Journal of the American Chemical Society, Vol. 78, Issue 10 https://doi.org/10.1021/ja01591a029	journal	May 1956
The Electron Diffraction Investigation of the Structure of Benzene, Pyridine, Pyrazine, Butadiene-1,3, Cyclopentadiene, Furan, Pyrrole, and Thiophene Schomaker, V.; Pauling, L. Journal of the American Chemical Society, Vol. 61, Issue 7 https://doi.org/10.1021/ja01876a038	journal	July 1939
Radical Cation Diels–Alder Cycloadditions by Visible Light Photocatalysis Lin, Shishi; Ischay, Michael A.; Fry, Charles G. Journal of the American Chemical Society, Vol. 133, Issue 48 https://doi.org/10.1021/ja2093579	journal	December 2011
Photosensitization of TiO ₂ by [Fe ^II (2,2‘-bipyridine-4,4‘-dicarboxylic acid) ₂ (CN) ₂ ]: Band Selective Electron Injection from Ultra-Short-Lived Excited States Ferrere, Suzanne; Gregg, Brian A. Journal of the American Chemical Society, Vol. 120, Issue 4 https://doi.org/10.1021/ja973504e	journal	February 1998
Lability and Basicity of Bipyridine-Carboxylate-Phosphonate Ligand Accelerate Single-Site Water Oxidation by Ruthenium-Based Molecular Catalysts Shaffer, David W.; Xie, Yan; Szalda, David J. Journal of the American Chemical Society, Vol. 139, Issue 43 https://doi.org/10.1021/jacs.7b06096	journal	October 2017
Preparation of 5-Brominated and 5,5‘-Dibrominated 2,2‘-Bipyridines and 2,2‘-Bipyrimidines Schwab, Peter F. H.; Fleischer, Frank; Michl, Josef The Journal of Organic Chemistry, Vol. 67, Issue 2 https://doi.org/10.1021/jo010707j	journal	January 2002
The preparation and properties of certain pyridylpyrimidines and bidiazines as potential chelating agents for iron(II) Lafferty, John J.; Case, Francis H. The Journal of Organic Chemistry, Vol. 32, Issue 5 https://doi.org/10.1021/jo01280a064	journal	May 1967
Photoredox Catalysts: Synthesis of the Bipyrazine Ligand Graaf, Matthew D.; Moeller, Kevin D. The Journal of Organic Chemistry, Vol. 80, Issue 3 https://doi.org/10.1021/jo502925u	journal	January 2015
A stable quasi-solid-state dye-sensitized solar cell with an amphiphilic ruthenium sensitizer and polymer gel electrolyte Wang, Peng; Zakeeruddin, Shaik M.; Moser, Jacques E. Nature Materials, Vol. 2, Issue 6 https://doi.org/10.1038/nmat904	journal	May 2003
Structural, electrochemical and photophysical properties of an exocyclic di-ruthenium complex and its application as a photosensitizer Salpage, Sahan R.; Paul, Avishek; Som, Bozumeh Dalton Transactions, Vol. 45, Issue 23 https://doi.org/10.1039/C6DT01377E	journal	January 2016
Electron and energy transfer in donor–acceptor systems with conjugated molecular bridges Albinsson, Bo; Eng, Mattias P.; Pettersson, Karin Physical Chemistry Chemical Physics, Vol. 9, Issue 44 https://doi.org/10.1039/b706122f	journal	January 2007
Long-range proton-coupled electron transfer in phenol–Ru(2,2′-bipyrazine)32+ dyads Bronner, Catherine; Wenger, Oliver S. Physical Chemistry Chemical Physics, Vol. 16, Issue 8 https://doi.org/10.1039/c3cp55071k	journal	January 2014
A voyage into the synthesis and photophysics of homo- and heterobinuclear ensembles of phthalocyanines and porphyrins de la Torre, Gema; Bottari, Giovanni; Sekita, Michael Chemical Society Reviews, Vol. 42, Issue 20 https://doi.org/10.1039/c3cs60140d	journal	January 2013
OLEX2 : a complete structure solution, refinement and analysis program Dolomanov, Oleg V.; Bourhis, Luc J.; Gildea, Richard J. Journal of Applied Crystallography, Vol. 42, Issue 2 https://doi.org/10.1107/S0021889808042726	journal	January 2009
Crystal structure refinement with SHELXL Sheldrick, George M. Acta Crystallographica Section C Structural Chemistry, Vol. 71, Issue 1, p. 3-8 https://doi.org/10.1107/S2053229614024218	journal	January 2015
Diethyl 2,2′-bipyridine-4,4′-dicarboxylate Rillema, D. Paul; Moore, Curtis; KomReddy, Venugopal IUCrData, Vol. 1, Issue 10 https://doi.org/10.1107/S2414314616015479	journal	October 2016
Methyl 5-methylpyrazine-2-carboxylate Rillema, D. Paul; KomReddy, Venugopal; Senaratne, Nilmini K. IUCrData, Vol. 2, Issue 7 https://doi.org/10.1107/S241431461700997X	journal	July 2017
5-Methylpyrazine-2-carboxamide Rillema, D. Paul; Senaratne, Nilmini K.; Moore, Curtis IUCrData, Vol. 2, Issue 7 https://doi.org/10.1107/S2414314617010902	journal	July 2017
Tryptophan-Accelerated Electron Flow Through Proteins Shih, C.; Museth, A. K.; Abrahamsson, M. Science, Vol. 320, Issue 5884 https://doi.org/10.1126/science.1158241	journal	June 2008
Pyrazine derivatives: a patent review (June 2012 – present) Dolezal, Martin; Zitko, Jan Expert Opinion on Therapeutic Patents, Vol. 25, Issue 1 https://doi.org/10.1517/13543776.2014.982533	journal	December 2014
Two Organic Cation Salts Containing Tetra(isothiocyanate)cobaltate(II): Synthesis, Crystal Structures, Spectroscopic, Optical and Magnetic Properties Zhang, Zheng; Xu, Junwei; Yan, Sisi Crystals, Vol. 7, Issue 3 https://doi.org/10.3390/cryst7030092	journal	March 2017
An improved procedure for the preparation of Ru(bpz) ₃ (PF ₆ ) ₂ via a high-yielding synthesis of 2,2’-bipyrazine Schultz, Danielle M.; Sawicki, James W.; Yoon, Tehshik P. Beilstein Journal of Organic Chemistry, Vol. 11 https://doi.org/10.3762/bjoc.11.9	journal	January 2015

Similar Records

Spectroelectrochemical properties of ruthenium(II) tris chelate complexes 2,2'-bipyrimidine and 2,2'-bipyrazine

Journal Article · 1987 · Inorg. Chem.; (United States) · OSTI ID:5522182

Tait, C D; Donohoe, R J; DeArmond, M K; +1 more

Synthesis and antitumor activity evaluation of different 2,5-dialkyloxazolopyrano[3,2-c]quinolinone derivatives

Journal Article · 2019 · Medicinal Chemistry Research (Print) · OSTI ID:22936219

Hassanin, Hany M.; Abd Elmoneam, Wafaa R.

Synthesis and characterization of monometallic and bimetallic mixed-ligand complexes of iron(II) containing 2,2'-bipyrimidine or 2,3-bis(2-pyridyl)pyrazine

Journal Article · 1987 · Inorg. Chem.; (United States) · OSTI ID:5794984

Brewer, K J; Murphy, Jr, W R; Petersen, J D

Title: Synthesis and Characterization of 2‐(2‐Pyridinyl)pyrazine and 2,2′‐Bipyrazine Derivatives

Citation Formats

References (35)

Similar Records

Related Subjects