Exploring the reactivity of halogen-free aminopyridines in one-pot palladium-catalyzed C–N cross-coupling/C–H functionalization

Santos, A. Sofia; Martins, M. Margarida; Mortinho, Ana C.; Silva, Artur M. S.; Marques, M. Manuel B.

doi:10.1016/j.tetlet.2020.152303

Cited by 3 publications

(6 citation statements)

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“… [31] Furthermore, t BuOK has been reported as the sole additive in a novel radical condensation reaction [34] for the transamidation of primary and tertiary amides at room temperatures, giving access to secondary amides. [35] In continuation of our interest in developing synthetic methodologies to access N ‐heterocycles, such as azaindoles and indoles,[ 36 , 37 , 38 , 39 , 40 ] we envisaged to investigate the synthesis of BIMs.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Bis(3‐indolyl)methanes Mediated by Potassium tert‐Butoxide

et al. 2023

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The indole moiety is an important N-heterocycle found in natural products, and a key structural component of many value-added chemicals including pharmaceuticals. In particular, bis(3-indolyl)methanes (BIMs) are an important subgroup of indoles, composed of two indole units. Herein, we report the development of a simple method to access BIMs derivatives in yields of up to 77 % by exploiting a tBuOK-mediated coupling reaction of indoles and benzyl alcohols.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Bis(3‐indolyl)methanes Mediated by Potassium tert‐Butoxide

et al. 2023

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“…4 We have been particularly interested in metal-catalyzed methods to prepare N-heterocycles via imine formation. 5,6 Traditionally, imines are synthesized via condensation of an aldehyde or ketone with a primary amine in the presence of an acid catalyst. Recently, catalytic methods to prepare imines have emerged, [7][8][9] especially involving the use of Earth-abundant metals, such as manganese and nickel, for the dehydrogenation of alcohols and subsequent reaction with amine.…”

Section: Figure 1 Representative Examples Of Bioactive Indole Compoundsmentioning

confidence: 99%

Bimetallic Catalyzed Synthesis of 2-Arylindoles

et al. 2023

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A bimetallic synthesis of 2-arylindoles from alcohols and anilines is described. The dehydrogenation or oxidation of a secondary alcohol were performed by Ni- and Mn-catalyzed reactions, respectively. The formed ketone was converted into an imine intermediate that was later cyclized to the corresponding 2-arylindole by a Pd-catalyzed oxidative cyclization. A set of 2-arylindoles was prepared, without isolation of the intermediates generated. The compatibility of the catalysts was investigated, and the optimized protocol opens room for the integration of Earth abundant metals and palladium complexes to improve the sustainability of the synthesis of N-heterocycles.

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“…The results obtained demonstrate that this methodology exhibits a wide scope and compatibility with electron-withdrawing and electron-donating groups (Scheme 15). Marques and co-workers envisaged that halogen-free aminopyridines would provide straightforward access to azaindole derivatives via a C-H functionalization reaction [50]. Thus, the group developed a study consisting of the investigation of aminopyridine-based key synthetic intermediate (imine/enamine) generated via a Pdmediated reaction according to a previous report [45] under C-H functionalization conditions.…”

Section: Scheme 4 Synthesis Of Quinazolinones Via An Acceptorless Coupling Of O-aminobenzamidesmentioning

confidence: 99%

“…In this study, five different aminopyridines were tested to explore the influence of the position of the pyridine nitrogen and the methoxy group on the outcome of the reactions (Scheme 16). [50].…”

Section: Scheme 4 Synthesis Of Quinazolinones Via An Acceptorless Coupling Of O-aminobenzamidesmentioning

confidence: 99%

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Advances in Green Catalysis for the Synthesis of Medicinally Relevant N-Heterocycles

et al. 2021

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N-heterocycles, both saturated and unsaturated, are ubiquitous biologically active molecules that are extremely appealing scaffolds in drug discovery programs. Although classical synthetic methods have been developed to access many relevant N-heterocyclic scaffolds, representing well-established and reliable routes, some do not meet the needs of sustainability. In this context, several advances have been made towards the sustainable synthesis of N-heterocycles. This review focuses on the most recent examples from the last five years of catalytic synthesis of several heterocyclic compounds of medicinal relevance. Thus, the synthesis of isoindoloquinazolines, quinazolines and azaindoles, among others, are covered. The synthetic methods selected include the use of homogeneous and heterogeneous catalysts and the use of alternative and sustainable methods such as, for example, metal-catalyzed acceptorless coupling and one-pot reactions. The green aspects of the individual synthetic approaches are highlighted, and the scope of each methodology is described.

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Exploring the reactivity of halogen-free aminopyridines in one-pot palladium-catalyzed C–N cross-coupling/C–H functionalization

Cited by 3 publications

References 30 publications

Synthesis of Bis(3‐indolyl)methanes Mediated by Potassium tert‐Butoxide

Synthesis of Bis(3‐indolyl)methanes Mediated by Potassium tert‐Butoxide

Bimetallic Catalyzed Synthesis of 2-Arylindoles

Advances in Green Catalysis for the Synthesis of Medicinally Relevant N-Heterocycles

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