Palladium-Catalyzed Intermolecular Carbene Insertion Prior to Intramolecular Heck Cyclization: Synthesis of 2-Arylidene-3-aryl-1-indanones

Arunprasath, Dhanarajan; Muthupandi, Pandi; Sekar, Govindasamy

doi:10.1021/acs.orglett.5b02803

Cited by 35 publications

(18 citation statements)

References 62 publications

(14 reference statements)

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“…[46] One of the most common metals for the synthesis of 5-membered carbocycles via ATC processes is palladium. [47] Garbriele et al recently used a palladium ATC method for the synthesis of substituted indanes 71 (Scheme 16). [48] Palladium-catalysed reaction of phenylacetylenes 67 with amines 68 in the presence of carbon monoxide lead to a carbamoylation reaction that afforded propargyl-amides 69. syn-Carbocyclisation of alkynes 69 via intramolecular attack of palladium stabilised enolates 70 afforded, after proto-depalladation, (E)- [49] In a report analogous to that of Barluenga et al outlined above (cf.…”

Section: -Membered Carbocyclesmentioning

confidence: 99%

Auto‐Tandem Catalysis: Activation of Multiple, Mechanistically Distinct Process by a Single Catalyst

Camp

2016

Eur J Org Chem

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Auto‐tandem catalysis (ATC) is a powerful method for the synthesis of heterocycles and carbocycles as well as acyclic compounds. The process is defined as a single reagent catalysing multiple, mechanistically distinct processes of a chemical reaction. In this review recent advances in ATC using transition metal catalysts is described. In particular, the use of different catalytic systems for the controlled synthesis of the desired product, enantioselective synthesises in which multiple bonds are formed and mechanistic investigations are illustrated with applications to the synthesis of heterocycles and carbocycles as well as acyclic compounds. New approaches that use earth abundant catalysts, greener solvents or increased catalyst efficiency are highlighted. Examples of ATC reaction development are also included. In addition, ATC processes are used as key steps in the synthesis of natural products as well as biologically active compounds.

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Section: -Membered Carbocyclesmentioning

confidence: 99%

Auto‐Tandem Catalysis: Activation of Multiple, Mechanistically Distinct Process by a Single Catalyst

Camp

2016

Eur J Org Chem

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“…This compound was obtained as white solid, yield 96%; mp 205–208°C (Lit. mp 204–206°C); ir (KBr): 513, 700, 748, 822, 964, 1097, 1255, 1292, 1255, 1292, 1321, 1481, 1587, 1614 (C═C str. ), 1691 (C═O str.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Indane‐Based 1,5‐Benzothiazepines Derived from 3‐Phenyl‐2,3‐dihydro‐1H‐inden‐1‐one and Antimicrobial Studies Thereof

Mor

Nagoria

Sindhu

et al. 2017

Journal of Heterocyclic Chem

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In the present study, a series of 20 indane‐based 1,5‐benzothiazepines (5a–t) has been prepared derived from 3‐phenyl‐2,3‐dihydro‐1H‐inden‐1‐one (1). All the synthesized 1,5‐benzothiazepines (5a–t) were screened for their in vitro antimicrobial activities against four bacteria [Bacillus subtilis (MTCC 441), Staphylococcus epidermidis (MTCC 6880), Escherichia coli (MTCC 1652), and Pseudomonas aeruginosa (MTCC 424)] and two fungi [Candida albicans (MTCC 227) and Aspergillus niger (MTCC 8189)]. Among all the tested derivatives, 5n and 5o against E. coli displayed more inhibitory activity than that of the reference drug, ciprofloxacin, while the derivatives 5c, 5m–o, 5s, and 5t against C. albicans, and 5d, 5e, 5n, 5o, 5s, and 5t against A. niger were found to be more potent than the standard drug, that is, fluconazole.

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“…High resolution mass spectra (HRMS) were recorded on Waters‐Q‐Tof Micro mass spectrometer. Diaryl disulfides and N ‐tosylhydrazones were synthesized using a reported literature procedure.…”

Section: Methodsmentioning

confidence: 99%

A Transition‐Metal‐Free and Base‐Mediated Carbene Insertion into Sulfur‐Sulfur and Selenium‐Selenium Bonds: An Easy Access to Thio‐ and Selenoacetals

Arunprasath

Sekar

2016

Adv Synth Catal

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A transition-metal-free and base-mediated carbene insertion across sulfur-sulfur and selenium-selenium bonds has been developed by employing N-tosylhydrazone as a stable and safe carbene precursor. The ylide formation from carbene followed by Stevens rearrangement are considered to be the key steps. This thiol and selenolfree protocol delivers thioacetals and selenoacetals in good to excellent yields in short reaction time with good functional group tolerance. A one-pot synthesis involving in situ generation of tosylhydrazone has also been demonstrated.

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Palladium-Catalyzed Intermolecular Carbene Insertion Prior to Intramolecular Heck Cyclization: Synthesis of 2-Arylidene-3-aryl-1-indanones

Cited by 35 publications

References 62 publications

Auto‐Tandem Catalysis: Activation of Multiple, Mechanistically Distinct Process by a Single Catalyst

Auto‐Tandem Catalysis: Activation of Multiple, Mechanistically Distinct Process by a Single Catalyst

Synthesis of Indane‐Based 1,5‐Benzothiazepines Derived from 3‐Phenyl‐2,3‐dihydro‐1H‐inden‐1‐one and Antimicrobial Studies Thereof

A Transition‐Metal‐Free and Base‐Mediated Carbene Insertion into Sulfur‐Sulfur and Selenium‐Selenium Bonds: An Easy Access to Thio‐ and Selenoacetals

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