Transition-metal-catalyzed intramolecular cyclization of amido(hetero)arylboronic acid aldehydes to isoquinolinones and derivatives

Marques, Carolina S.; Peixoto, Daniela; Burke, Anthony J.

doi:10.1039/c5ra00404g

Cited by 18 publications

(4 citation statements)

References 79 publications

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“…Alternatively, arylation addition reactions of organoboron reagents to aldehydes have become more prevalent using transition-metal catalysts such as Ni (0), − Pd(II), , Cu(I/II), − Fe(III), Ru(II), , Zn(II), Ir(I), Co(II), and Rh(I)/(II) complexes. − Among the catalysts, the most heavily studied and robust one was shown to be [Rh( COD )Cl 2 ] , as it does not require any additional resources and conditions, such as a microwave, glovebox, additional ligands, anhydrous solvents, and inert atmosphere. Therefore, it was decided to attempt this reaction using a modified Miyaura arylation via [Rh( COD )Cl 2 ], ,, involving the addition of an aromatic boronic acid to aldehyde 6 .…”

Section: Resultsmentioning

confidence: 99%

“…Fortunately, after optimization (Scheme and Table , entry 5), this procedure ultimately yielded the desired alcohol as a diastereomeric mixture 3.3:1 of anti and syn alcohols 5a and 5b in a good yield of 75%. This result was achieved under non-anhydrous conditions, a significant benefit over the formation of reactive organometallic species previously used for C–C bond-forming reactions used for benzodioxane-containing lignans. − This work also signified that Miyaura arylation using [Rh( COD )Cl 2 ] was also possible on more complex aldehydes that were used in the methodology development. − …”

Section: Resultsmentioning

confidence: 99%

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Total Synthesis of Linear Coumarniolignoids (+) and (−)-Sapiumin C, (−)-Moluccanin, and (−)-Hemidesminine

2023

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Coumarinolignoids (CLs) are a class of natural products isolated from a diverse range of plant species. Due to their unique structural scaffold, they exhibit a wide range of interesting biological activities including hepatoprotective, antitumor, antiinflammatory, and antioxidant activities among others. In this research, key intermediate 10 was used to stereoselectively synthesize CLs (7′S,8′S)-and (7′R,8′R)-sapiumin C 1 and 2, (7′S,8′S)-moluccanin 3, and (7′S,8′S) hemidesminine 4 for the first time, establishing a versatile synthetic method for the stereoselective synthesis of linear CLs. The developed method includes a Mitsunobu coupling, a modified Miyaura arylation via a rhodium catalyst, and an acid-catalyzed cyclization in key bondforming steps. The developed synthetic route allows the synthesis of both enantiomers of a given natural product from the same chiral pool reagent (S)-solketal while allowing easy variation of aromatic substitution and hydroxymethyl/allylhydroxymethyl moieties that are common in this class of natural products.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Total Synthesis of Linear Coumarniolignoids (+) and (−)-Sapiumin C, (−)-Moluccanin, and (−)-Hemidesminine

2023

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“…In an earlier report by our group [24], an innovative transitionmetal-catalysed intramolecular cyclization reaction of amido(hetero)arylboronic acid aldehydes to isoquinolin-1(2H)-one derivatives was developed. Starting from easily accessed acetal substrates, an efficient three-step synthetic approach was reported [24] (Scheme 1).…”

Section: Chemical Synthesismentioning

confidence: 99%

“…Starting from easily accessed acetal substrates, an efficient three-step synthetic approach was reported [24] (Scheme 1). A library of 16 isoquinolinone and azepanone derivatives (Schemes 1 and 2) were tested for cholinesterase inhibition.…”

Section: Chemical Synthesismentioning

confidence: 99%

New cholinesterase inhibitors for Alzheimer’s disease: Structure Activity Studies (SARs) and molecular docking of isoquinolone and azepanone derivatives

Bacalhau

Juan

Marques

et al. 2016

Bioorganic Chemistry

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a b s t r a c tA library of isoquinolinone and azepanone derivatives were screened for both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) activity. The strategy adopted included (a) in vitro biological assays, against eel AChE (EeAChE) and equine serum BuChE (EqBuChE) in order to determine the compounds IC 50 and their dose-response activity, consolidated by (b) molecular docking studies to evaluate the docking poses and interatomic interactions in the case of the hit compounds, validated by STD-NMR studies. Compound (1f) was identified as one of these hits with an IC 50 of 89.5 lM for EeAChE and 153.8 lM for EqBuChE, (2a) was identified as a second hit with an IC 50 of 108.4 lM (EeAChE) and 277.8 lM (EqBuChE). In order to gain insights into the binding mode and principle active site interactions of these molecules, (R)-(1f) along with 3 other analogues (also as the R-enantiomer) were docked into both RhAChE and hBuChE models. Galantamine was used as the benchmark. The docking study was validated by performing an STD-NMR study of (1f) with EeAChE using galantamine as the benchmark.

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Transition Metal Catalyst‐Free, Base‐Promoted 1,2‐Additions of Polyfluorophenylboronates to Aldehydes and Ketones

et al. 2021

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An ovel protocol for the transition metal-free 1,2addition of polyfluoroaryl boronate esters to aldehydes and ketones is reported, which provides secondary alcohols,tertiary alcohols,a nd ketones.C ontrol experiments and DFT calculations indicate that both the ortho-F substituents on the polyfluorophenyl boronates and the counterion K + in the carbonate base are critical. The distinguishing features of this procedure include the employment of commercially available starting materials and the broad scope of the reaction with aw ide variety of carbonyl compounds giving moderate to excellent yields.I ntriguing structural features involving O À H•••O and O À H•••N hydrogen bonding,a sw ell as areneperfluoroarene interactions,inthis series of racemic polyfluoroaryl carbinols have also been addressed.

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Transition-metal-catalyzed intramolecular cyclization of amido(hetero)arylboronic acid aldehydes to isoquinolinones and derivatives

Cited by 18 publications

References 79 publications

Total Synthesis of Linear Coumarniolignoids (+) and (−)-Sapiumin C, (−)-Moluccanin, and (−)-Hemidesminine

Total Synthesis of Linear Coumarniolignoids (+) and (−)-Sapiumin C, (−)-Moluccanin, and (−)-Hemidesminine

New cholinesterase inhibitors for Alzheimer’s disease: Structure Activity Studies (SARs) and molecular docking of isoquinolone and azepanone derivatives

Transition Metal Catalyst‐Free, Base‐Promoted 1,2‐Additions of Polyfluorophenylboronates to Aldehydes and Ketones

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