Synthesis of Pyridazine Dicarboxamides via Highly Selective Palladium‐catalyzed Aminocarbonylation

Szőke, Gyöngyi; Takács, Attila; Kollár, László

doi:10.1002/jhet.2523

Cited by 5 publications

(3 citation statements)

References 25 publications

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“…The Pd-catalyzed aminocarbonylation of 3,6-diiodopyridazine with several primary and secondary amines (including amino acid esters) resulted in 3,6-diamides in moderate to high yield in chemoselective reactions. The lack of double carbonylation product was explained by the close proximity of the aromatic ring nitrogen to the iodo substituent (Figure 6) [44]. The reactions of iodobenzene and iodoalkenes such as 1-iodocyclohexene, 4-tertbutyl-1-iodocyclohexene, α-iodostyrene, and 17-iodoandrost-16-ene with the free radical 4-amino-TEMPO afforded amides and ketoamides for iodobenzene and selectively amides for all the other cases.…”

Section: Reactions In Conventional Solventsmentioning

confidence: 99%

27 Years of Catalytic Carbonylative Coupling Reactions in Hungary (1994–2021)

2022

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Palladium-catalyzed carbonylation reactions, in the presence of nucleophiles, serve as very potent tools for the conversion of aryl and alkenyl halides or halide equivalents to carboxylic acid derivatives or to other carbonyl compounds. There are a vast number of applications for the synthesis of simple building blocks as well as for the functionalization of biologically important skeletons. This review covers the history of carbonylative coupling reactions in Hungary between the years 1994 and 2021.

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Section: Reactions In Conventional Solventsmentioning

confidence: 99%

27 Years of Catalytic Carbonylative Coupling Reactions in Hungary (1994–2021)

2022

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“…Several α,β-unsaturated carboxamides and aryl carboxamides, using palladium-catalyzed aminocarbonylation as a key reaction, were recently synthesized in our laboratory [ 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 ]. Just to illustrate the most recent developments, the functionalization of aromatic N -heterocycles in aminocarbonylation should be mentioned [ 46 , 47 , 48 , 49 ].…”

Section: Introductionmentioning

confidence: 99%

Selective Synthesis of N-Acylnortropane Derivatives in Palladium-Catalysed Aminocarbonylation

et al. 2021

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The aminocarbonylation of various alkenyl and (hetero)aryl iodides was carried out using tropane-based amines of biological importance, such as 8-azabicyclo[3.2.1]octan-3-one (nortropinone) and 3α-hydroxy-8-azabicyclo[3.2.1]octane (nortropine) as N-nucleophile. Using iodoalkenes, the two nucleophiles were selectively converted to the corresponding amide in the presence of Pd(OAc)2/2 PPh3 catalysts. In the presence of several iodo(hetero)arenes, the application of the bidentate Xantphos was necessary to produce the target compounds selectively. The new carboxamides of varied structure, formed in palladium-catalyzed aminocarbonylation reactions, were isolated and fully characterized. In this way, a novel synthetic method has been developed for the producing of N-acylnortropane derivatives of biological importance.

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“…In our research group, several iodoheteroaromatic model substrates have been successfully used in palladium-catalyzed aminocarbonylation to introduce an amide motif into their heteroaryl core, justifying the effectiveness of this homogeneous synthetic method [ 59 , 60 , 61 , 62 , 63 , 64 , 65 ]. As a part of our ongoing research, we were interested in the use of the homogeneous catalytic aminocarbonylation of 6-iodoquinoline substrate with various amines in order to design a library of new 6-functionalized quinoline derivatives, keeping in mind our main goal to access to scarce quinoline-6-glyoxylamides that could be the object of future biological investigations.…”

Section: Introductionmentioning

confidence: 99%

Highly Selective Synthesis of 6-Glyoxylamidoquinoline Derivatives via Palladium-Catalyzed Aminocarbonylation

et al. 2021

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The aminocarbonylation of 6-iodoquinoline has been investigated in the presence of large series of amine nucleophiles, providing an efficient synthetic route for producing various quinoline-6-carboxamide and quinoline-6-glyoxylamide derivatives. It was shown, after detailed optimization study, that the formation of amides and ketoamides is strongly influenced by the reaction conditions. Performing the reactions at 40 bar of carbon monoxide pressure in the presence of Pd(OAc)2/2 PPh3, the corresponding 2-ketocarboxamides were formed as major products (up to 63%). When the monodentate triphenylphosphine was replaced by the bidentate XantPhos, the quinoline-6-carboxamide derivatives were synthesized almost exclusively under atmospheric conditions (up to 98%). The isolation and characterization of the new carbonylated products of various structures were also accomplished. Furthermore, the structure of three new mono- and double-carbonylated compounds were unambiguously established by using a single-crystal XRD study.

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Synthesis of Pyridazine Dicarboxamides via Highly Selective Palladium‐catalyzed Aminocarbonylation

Cited by 5 publications

References 25 publications

27 Years of Catalytic Carbonylative Coupling Reactions in Hungary (1994–2021)

27 Years of Catalytic Carbonylative Coupling Reactions in Hungary (1994–2021)

Selective Synthesis of N-Acylnortropane Derivatives in Palladium-Catalysed Aminocarbonylation

Highly Selective Synthesis of 6-Glyoxylamidoquinoline Derivatives via Palladium-Catalyzed Aminocarbonylation

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