Synthesis of phenanthridine and its analogues via aerobic ligand-free domino Suzuki coupling–Michael addition reaction catalyzed by in situ generated palladium-nanoparticles in water

Ghosh, Munmun; Ahmed, Atiur; Dhara, Shubhendu; Ray, Jayanta K.

doi:10.1016/j.tetlet.2013.06.089

Cited by 28 publications

(14 citation statements)

References 37 publications

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“…Ghosh, Dhara et al also reported a synthesis of substituted phenanthridines based on palladium-mediated Suzuki coupling ( Scheme 14 ) [ 34 – 35 ]. Aerobic ligand-free domino Suzuki coupling–Michael addition reaction in the presence of Pd(OAc) 2 and K 3 PO 4 as a catalytic system in H 2 O was catalysed by palladium nanoparticles, that were generated in situ in water with the elimination of acetone.…”

Section: Reviewmentioning

confidence: 99%

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Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

Tumir¹,

Stojković²,

Piantanida³

2014

Beilstein J. Org. Chem.

133

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SummaryPhenanthridine derivatives are one of the most intensively studied families of biologically active compounds with efficient DNA binding capability. Attracting attention since DNA structure discovery (1960s), they were early recognized as a symbol of DNA intercalative binding, for many decades applied as gold-standard DNA- and RNA-fluorescent markers (ethidium bromide), probes for cell viability (propidium iodide), but also “ill-famed” for various toxic (genotoxic) and mutagenic effects. After two decades of low interest, the discovery of phenanthridine alkaloids and new studies of antiparasitic/antitumor properties of phenanthridine derivatives resulted in the strong increase of the scientific interest about the turn of this century. Here are summarized phenanthridine-related advances in the 21st century (2000-present period) with emphasis on the supramolecular interactions and bioorganic chemistry, as well as novel or improved synthetic approaches.

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Section: Reviewmentioning

confidence: 99%

“… Aerobic domino Suzuki coupling combined with Michael addition reaction in the presence of a Pd(OAc) 2 /K 3 PO 4 catalytic system in water [ 34 – 35 ]. …”

Section: Reviewmentioning

confidence: 99%

Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

Tumir¹,

Stojković²,

Piantanida³

2014

Beilstein J. Org. Chem.

133

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“…8‐Fluorophenanthridine (3d): 13 Compound 3d was prepared according to the general experimental procedure as above; Yield: 0.175 g (89 %); reddish brown sticky mass. 1 H NMR (500 MHz, CDCl 3 ): δ = 9.19 (s,1 H), 8.55 (dd, J = 8.9, 4.9 Hz, 1 H), 8.47 (d, J = 7.8 Hz, 1 H), 8.18 (d, J = 7.9 Hz, 1 H), 7.50–7.79 (m, 4 H) ppm.…”

Section: Methodsmentioning

confidence: 99%

“…Additionally, cascade approaches using easily achievable starting materials offer a more atom‐economical approach relative to other conventional reactions. In this regard, Pd‐mediated Ullmann cross‐coupling/reductive cyclization,12 Suzuki cross‐coupling/Michael addition reaction13 or condensation14 sequences are well‐known approaches for quinolines, isoquinolones, and phenanthridines. However, in the Pd‐mediated Ullmann cross‐coupling cascade approach, homocoupled side‐products are formed together with the desired product.…”

Section: Introductionmentioning

confidence: 99%

Cascade C–C and C–N Bond Formation: A Straightforward Synthesis of Phenanthridines and Fused Quinolines

Borah

Gogoi

2016

Eur J Org Chem

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A Pd‐catalyzed cascade process has been developed for the synthesis of quinoline and phenanthridine derivatives from various β‐chloro α,β‐unsaturated aldehydes and 2‐chloroaryl aldehydes, respectively, in good to high yields. The reaction proceeds through Pd‐catalyzed cascade carbon–carbon and carbon–nitrogen bond formation in a single reaction vessel. The requisite β‐chloro α,β‐unsaturated aldehydes were efficiently synthesized from their corresponding carbonyl compounds. The use of the ligand Sphos with Pd(OAc)2 is crucial for the successful implementation of the present cascade process. This synthetic protocol is also applied for the gram‐scale synthesis of a trispheridine alkaloid.

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“…In this regard, many studies have been focused on the development of efficient synthetic methodologies for the synthesis of such compounds. Reported synthetic strategies mainly rely on C–H functionalizations,, reductions, dehydrations, intermolecular annulations, intramolecular cyclizations and other methods . However, the applicability of those methods is often limited with regard to the preparative scope.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Benzoacridines and Benzophenanthridines by Regioselective Pd‐Catalyzed Cross‐Coupling Reactions Followed by Acid‐Mediated Cycloisomerizations

et al. 2019

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A convenient synthesis of various benzoacridines and benzophenanthridines from readily available dihalogenated quinolines is reported. The synthesis is based on regioselective Suzuki and Sonogashira reactions followed by Brønsted acid‐mediated cycloisomerization. The developed methodology is highly modular and allows the construction of various ring systems and substitution patterns in high yields. The optical and electrochemical properties of selected derivatives were investigated.

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Synthesis of phenanthridine and its analogues via aerobic ligand-free domino Suzuki coupling–Michael addition reaction catalyzed by in situ generated palladium-nanoparticles in water

Cited by 28 publications

References 37 publications

Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

Cascade C–C and C–N Bond Formation: A Straightforward Synthesis of Phenanthridines and Fused Quinolines

Synthesis of Benzoacridines and Benzophenanthridines by Regioselective Pd‐Catalyzed Cross‐Coupling Reactions Followed by Acid‐Mediated Cycloisomerizations

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Synthesis of phenanthridine and its analogues via aerobic ligand-free domino Suzuki coupling–Michael addition reaction catalyzed by in situ generated palladium-nanoparticles in water

Cited by 28 publications

References 37 publications

Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

Cascade C–C and C–N Bond Formation: A Straightforward Synthesis of Phenanthridines and Fused Quinol­ines

Synthesis of Benzoacridines and Benzophenanthridines by Regioselective Pd‐Catalyzed Cross‐Coupling Reactions Followed by Acid‐Mediated Cycloisomerizations

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Cascade C–C and C–N Bond Formation: A Straightforward Synthesis of Phenanthridines and Fused Quinolines