Route to benzo- and pyrido-fused 1,2,4-triazinyl radicals via N'-(het)aryl-N'-[2-nitro(het)aryl]hydrazides

The Journal of Organic Chemistry
Andrey A BerezinPanayiotis A Koutentis

Abstract

A two-step route to 1,3-disubstituted benzo- and pyrido-fused 1,2,4-triazinyl radicals is presented. The route involves the N'-(2-nitroarylation) of easily prepared N'-(het)arylhydrazides via nucleophilic aromatic substitution of 1-halo-2-nitroarenes, which in most cases gives N'-(het)aryl-N'-[2-nitro(het)aryl]hydrazides in good yields. Mild reduction of the nitro group followed by an acid-mediated cyclodehydration gives the fused triazines, which upon alkali treatment afford the desired radicals. Fifteen examples of radicals are presented bearing a range of substituents at N-1, C-3, and C-7, including the pyrid-2-yl and 8-aza analogues. This route to the N'-(het)aryl-N'-[2-nitro(het)aryl]hydrazides, which works well with benzo- and picolinohydrazides, required a modification for aceto- and trifluoroacetohydrazides that involved a multistep synthesis of asymmetrically 1,1-diaryl-substituted hydrazines.

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Citations

Feb 26, 2016·Organic Letters·Christos P ConstantinidesPiotr Kaszyński
Aug 6, 2015·Organic Letters·Christos P ConstantinidesPanayiotis A Koutentis
May 18, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Christos P ConstantinidesPanayiotis A Koutentis
Jul 21, 2016·Journal of the American Chemical Society·Marcin JasińskiPiotr Kaszyński
Jul 20, 2016·Journal of the American Chemical Society·Nolan M GallagherAndrzej Rajca
May 16, 2017·Nature Communications·Jacob A GrantAnnMarie C O'Donoghue
Jun 20, 2017·The Journal of Organic Chemistry·Anastasia C SavvaPanayiotis A Koutentis
Mar 8, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Lee-Ann J KeaneFawaz Aldabbagh
Dec 19, 2014·Organic & Biomolecular Chemistry·Ji-Quan ZhangAlbert S C Chan
Aug 12, 2016·Angewandte Chemie·Piotr KaszyńskiVictor G Young
Sep 12, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Rajendar NasaniSanjit Konar
Oct 2, 2020·Organic & Biomolecular Chemistry·Fergus J M RogersMichelle L Coote
Feb 6, 2017·Topics in Current Chemistry·Christian Friebe, Ulrich S Schubert
Jan 23, 2021·Physical Chemistry Chemical Physics : PCCP·Jessica ExnerArmido Studer
Aug 23, 2019·Organic Letters·Dominika PomikłoPiotr Kaszyński
Mar 1, 2019·Journal of the American Chemical Society·Nolan GallagherAndrzej Rajca
Aug 6, 2014·Journal of the American Chemical Society·Christos P ConstantinidesPanayiotis A Koutentis
Apr 25, 2020·Organic Letters·Paulina BartosPiotr Kaszyński
Mar 19, 2019·Nano Letters·Jonathan Z LowLatha Venkataraman
Jul 30, 2014·The Journal of Organic Chemistry·Agnieszka BodziochGreta Utecht
Dec 20, 2019·Organic Letters·Paulina BartosPiotr Kaszyński
Jun 27, 2018·The Journal of Organic Chemistry·Georgia A ZissimouPanayiotis A Koutentis
Jul 1, 2020·The Journal of Physical Chemistry. a·Fergus J M RogersMichelle L Coote
Sep 18, 2021·Organic Letters·Agnieszka BodziochPiotr Kaszyński

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