22948-94-3Relevant articles and documents
Structure, electronic, spectroscopic and reactivity investigations of pharmacologically active compound 1–acetyl–3–indolecarboxaldehyde – An experimental and theoretical approach
Durgadevi,Arjunan,Thirunarayanan,Marchewka,Mohan
, p. 57 - 69 (2018)
The experimental and theoretical studies on the structure and vibrations of 1–acetyl–3–indolecarboxaldehyde (AIC) have been carried out by utilising FT–IR, FT–Raman, FT–NMR and quantum chemical density functional theory (DFT) method. The FT–IR and FT–Raman spectra are recorded in the region 4000–400 cm?1 and 4000–100 cm?1, respectively. The geometry of AIC is optimised by B3LYP method with 6–31G** 6–311++G** and cc–pVTZ basis sets. The more stable minimum energy conformer has been found by analyzing the potential energy profile. The fundamental vibrational frequencies, infrared intensities, Raman intensities and bonding features of this compound are determined. The HOMO and LUMO energy difference show that, the charge transfer occurs within the molecule. The electrostatic potential and thermodynamic properties of the compound at the different temperatures have been calculated. 1H and 13C NMR chemical shifts of the compound are determined by Gauge Invariant Atomic Orbital (GIAO) by using B3LYP/6–311++G** method. The electrostatic potential of AIC lie in the range +1.22e × 10?2 to ?1.22e × 10?2. The limits of total electron density of the complex is +4.906e × 10?2 to ?4.906e × 10?2.
Spirocyclization reactions and antiproliferative activity of indole phytoalexins 1-methoxybrassinin and its 1-substituted derivatives
Budovská, Mariana,Pilátová, Martina Bago,Tischlerová, Viera,Moj?i?, Ján
, p. 198 - 234 (2016)
The effect of the reaction temperature and the solvent on the diastereoselectivity of the spirocyclization of 1-methoxybrassinin leading to 1-methoxyspirobrassinol methyl ether was studied. 1-Acyl derivatives of 1-methoxyspirobrassinol and 1-methoxyspirobrassinol methyl ether were prepared by the bromine-mediated spirocyclization reactions of derivatives of brassinin bearing an acyl group on the indole nitrogen with water or methanol as nucleophilic agents. The cyclization of 1-acyl derivatives of brassinin afforded the trans-diastereoisomer as the major product, whereas using 1-methoxybrassinin afforded the cis- and trans-isomers in a ratio near to 1:1. Bromospirocyclization of brassinin and 1-methylbrassinin in the presence of methanol resulted in the formation of spirobrassinin and 1-methylspirobrassinin. The newly synthesized analogues of indole phytoalexins exhibited more significant antiproliferative activity against human leukemia cell lines than the natural phytoalexins.
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Savel'eva et al.
, (1973)
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Selective Synthesis of Acylated Cross-Benzoins from Acylals and Aldehydes via N-Heterocyclic Carbene Catalysis
Onodera, Kou,Suzuki, Yumiko,Takashima, Ryo
supporting information, p. 4197 - 4202 (2021/06/27)
The utility of acylals as building blocks for selective cross-benzoin synthesis was explored in this study. The synthesis of α-acetoxyketones (O-acyl cross-benzoins) was achieved via selective N-heterocyclic carbene-catalyzed cross-benzoin reactions using acylals as aldehyde equivalents. Thus, the combination of ortho-substituted phenyl acylals and aromatic/aliphatic aldehydes as coupling substrates using bicyclic triazolium salts as precatalysts and potassium carbonate as a base in THF at reflux temperature selectively yielded O-acyl cross-benzoins.