Stereoselective Synthesis of Quaternary Benzylic Carbons Using C2 Symmetric Imidazolines and Tetrahydrofuran as Electrophile

We describe the syntheses and properties of five semi-rigid donor−(σ-bridge)−acceptor (D−σ−A) compounds. These compounds, which are candidates for incorporation in materials, have aniline-type donors and (mixed) cyano-and alkoxycarbonyl-1,1-difunctionalized vinyl acceptors that are separated by a four-σ-bond bridge. Their electronic properties were studied by means of photoelectron spectroscopy in combination with ab initio MO calculations, cyclic voltammetry, UVVis absorption spectroscopy, (time-resolved) fluorescence spectroscopy, and time-resolved microwave conductivity (TRMC). We found that these D−σ−A compounds exhibit a

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“…1 H NMR: δ = 1.21 (s, 9 H), 3.56 and 3.61 (A 2 B 2 , J = 6.3 Hz, 4 H) ppm. 13 C NMR: δ = 27.4, 43.6, 62.4, 73.5 ppm (in accordance with ref 69…”

Section: Methodssupporting

confidence: 84%

Photoinduced Charge Separation in Cyclohexylidene‐Based Donor−(σ‐Bridge)−Acceptor Compounds − Building Blocks for Materials

et al. 2003

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“…Respective commercially available nitriles (R 1 CN) were treated with HCl gas and ethanol in diethylether to give the imidoester hydrochloride 1 a – 1 i (Scheme ), which reacted in ethanol with 1,2‐benzenediamine to form the 2‐substituted benzimidazoles 2 a – 2 i via cyclocondensation 12. The 4′‐[(1 H ‐benzo[ d ]imidazol‐1‐yl)methyl]biphenyl‐2‐carbonitriles 3 a – 3 i were generated by N‐alkylation of 2 a – 2 i with 4′‐(bromomethyl)biphenyl‐2‐carbonitrile in dry DMF and NaH.…”

Section: Resultsmentioning

confidence: 99%

Characterization of New PPARγ Agonists: Benzimidazole Derivatives – the Importance of Position 2

et al. 2009

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Probing SAR: The 1-(biphenyl-4-ylmethyl)-1H-benzo[d]imidazole moiety is known to be an essential structural component of telmisartan for PPARgamma activation. This study focused on the substituents at position 2 of the benzimidazole in an attempt to optimize PPARgamma activation. In particular, the elongation of the alkyl chain and the introduction of an aromatic ring system were studied (shown).The relevance of substituents at C-2 of the central benzimidazole of telmisartan for PPARgamma activation has recently been demonstrated, and the most active compound identified in our previous work, 4'-[(2-propyl-1H-benzo[d]imidazol-1-yl)methyl]biphenyl-2-carboxylic acid (4 a), is used as lead structure in the present study. Modifications at C-2 included butyl (4 b), iso-butyl (4 c), tert-butyl (4 d), phenyl (4 e), benzyl (4 f), phenethyl (4 g), 4-chlorobenzyl (4 h), 4-methoxyphenyl (4 i), and 4-hydroxyphenyl (4 j) moieties. The compounds were tested in a differentiation assay using 3T3-L1 preadipocytes and a luciferase assay with COS-7 cells, transiently transfected with pGal4-hPPARgammaDEF, pGal5-TK-pGL3 and pRL-CMV, as established models for the assessment of cellular PPARgamma activation. The activity in the luciferase assay increased in the alkyl series: propyl (4 a)

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“…29 Accordingly, 1,3-imidazolidine 2 was prepared in excellent yield (98%) by condensation of diamine 1 with aqueous formaldehyde following the general procedure reported by Coldham et al 30,31 (Scheme 1). An important observation for this reaction is that the use of formaldehyde (37% aq.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and conformational analysis of novel tertiary amides derived from N-[(S)-α-phenylethyl]-1,3-imidazolidine

Santacruz-Jurez¹,

Hpfl²,

Huelgas³

et al. 2017

Arkivoc

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Stereoselective Synthesis of Quaternary Benzylic Carbons Using C₂ Symmetric Imidazolines and Tetrahydrofuran as Electrophile

Cited by 59 publications

References 47 publications

Photoinduced Charge Separation in Cyclohexylidene‐Based Donor−(σ‐Bridge)−Acceptor Compounds − Building Blocks for Materials

Photoinduced Charge Separation in Cyclohexylidene‐Based Donor−(σ‐Bridge)−Acceptor Compounds − Building Blocks for Materials

Characterization of New PPARγ Agonists: Benzimidazole Derivatives – the Importance of Position 2

Synthesis and conformational analysis of novel tertiary amides derived from N-[(S)-α-phenylethyl]-1,3-imidazolidine

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