One-Step Hydroxy Substitution of 4,4’-Dimethoxybenzhydrol with Amides, Lactams, Carbamates, Ureas and Anilines

Henneuse, Catherine; Boxus, Thierry; Tesolin, Lorenzo; Pantano, Guiseppe; Marchand‐Brynaert, Jacqueline

doi:10.1055/s-1996-4230

Cited by 25 publications

(18 citation statements)

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“…Subsequent Pinnick–Lindgren oxidation of the resultant imine afforded amide ( S )‐[ 18 F] 6 in 46 % RCC over three steps, all carried out in one pot, with a slightly decreased ee value of 83 %. Alternatively, the treatment of ( S )‐[ 18 F] 2 a with NH 2 CH( p ‐OMePh) 2 25 followed by Pinnick oxidation (30 min) then addition of trifluoroacetic acid (TFA; 10 min) afforded the primary α‐fluoroamide ( S )‐[ 18 F] 5 in 49 % RCC19 and 88 % ee . Finally, the formation of the chiral β‐fluoroamine ( S )‐[ 18 F] 7 was also possible from ( S )‐[ 18 F] 2 a by imine formation in dichloroethane (DCE) followed by reduction with sodium triacetoxyborohydride 26.…”

Section: Methodsmentioning

confidence: 99%

Organomediated Enantioselective ¹⁸F Fluorination for PET Applications

et al. 2015

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The first organomediated asymmetric (18)F fluorination has been accomplished using a chiral imidazolidinone and [(18)F]N-fluorobenzenesulfonimide. The method provides access to enantioenriched (18)F-labeled α-fluoroaldehydes (>90% ee), which are versatile chiral (18)F synthons for the synthesis of radiotracers. The utility of this process is demonstrated with the synthesis of the PET (positron emission tomography) tracer (2S,4S)-4-[(18)F]fluoroglutamic acid.

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Section: Methodsmentioning

confidence: 99%

Organomediated Enantioselective ¹⁸F Fluorination for PET Applications

et al. 2015

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“…Next, we successfully developed the oxidative amidation [24] of (S)-[ 18 Alternatively,t he treatment of (S)-[ 18 F]2a with NH 2 CH(p-OMePh) 2 [25] followed by Pinnick oxidation (30 min) then addition of trifluoroacetic acid (TFA; 10 min) afforded the primary a-fluoroamide (S)-[ 18 F]5 in 49 %RCC [19] and 88 % ee. Next, we successfully developed the oxidative amidation [24] of (S)-[ 18 Alternatively,t he treatment of (S)-[ 18 F]2a with NH 2 CH(p-OMePh) 2 [25] followed by Pinnick oxidation (30 min) then addition of trifluoroacetic acid (TFA; 10 min) afforded the primary a-fluoroamide (S)-[ 18 F]5 in 49 %RCC [19] and 88 % ee.…”

Section: Methodsmentioning

confidence: 99%

Organomediated Enantioselective ¹⁸F Fluorination for PET Applications

et al. 2015

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The first organomediated asymmetric 18 Ffluorination has been accomplished using ac hiral imidazolidinone and [ 18 F]N-fluorobenzenesulfonimide.The method provides access to enantioenriched 18 F-labeled a-fluoroaldehydes (> 90 %e e), whicha re versatile chiral 18 Fsynthons for the synthesis of radiotracers.T he utility of this process is demonstrated with the synthesis of the PET (positron emission tomography) tracer (2S,4S)-4-[ 18 F]fluoroglutamic acid.

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“…Disproportionation of benzhydrols in acidic media is well known [38] and has been studied in the case of 13 in particular. [39,40] In fact, heating of 13 in benzene solution containing catalytic amounts of para-toluenesulfonic acid, but in the absence of 8, yields benzophenone 11 and diveratrylmethane (12) in significant amounts (Scheme 4), along with condensation products.…”

Section: Synthesis Of 23671011-hexamethoxytribenzotriquinacene (3)mentioning

confidence: 99%

2,3,6,7,10,11‐Hexamethoxytribenzotriquinacene: Synthesis, Solid‐State Structure, and Functionalization of a Rigid Analogue of Cyclotriveratrylene

et al. 2004

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The syntheses of several tribenzotriquinacenes bearing six methoxy groups at the outer peripheral positions of the aromatic rings are reported. The centro‐methyl derivative is accessible in surprisingly good yield through two‐fold cyclodehydration in the final step of a synthesis route which requires special care in the preparation of some electron‐rich key intermediates, such as 5,6‐dimethoxy‐2‐methylindane‐1,3‐dione and bis(3,4‐dimethoxyphenyl)methanol. X‐ray single‐crystal structure analysis of the centro‐methyl derivative confirms its C3v‐symmetrical molecular structure but, at variance from the parent centro‐methyltribenzotriquinacene and the similarly shaped cyclotriveratrylene, the hexamethoxytribenzotriquinacene analog does not form columnar stacks in the solid state. Functionalization of the three benzhydrylic bridgehead positions leads to the tetramethyl analog and the bridgehead triol in good yields. In contrast, attempts to functionalize the ortho positions by nitration or bromination mainly give rise to ring cleavage through electrophilic ipso attack, which parallels the behavior of cyclotribenzylenes and cyclotriveratrylenes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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One-Step Hydroxy Substitution of 4,4’-Dimethoxybenzhydrol with Amides, Lactams, Carbamates, Ureas and Anilines

Cited by 25 publications

References 0 publications

Organomediated Enantioselective ¹⁸F Fluorination for PET Applications

Organomediated Enantioselective ¹⁸F Fluorination for PET Applications

Organomediated Enantioselective ¹⁸F Fluorination for PET Applications

2,3,6,7,10,11‐Hexamethoxytribenzotriquinacene: Synthesis, Solid‐State Structure, and Functionalization of a Rigid Analogue of Cyclotriveratrylene

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One-Step Hydroxy Substitution of 4,4’-Dimethoxybenzhydrol with Amides, Lactams, Carbamates, Ureas and Anilines

Cited by 25 publications

References 0 publications

Organomediated Enantioselective 18F Fluorination for PET Applications

Organomediated Enantioselective 18F Fluorination for PET Applications

Organomediated Enantioselective 18F Fluorination for PET Applications

2,3,6,7,10,11‐Hexamethoxytribenzotriquinacene: Synthesis, Solid‐State Structure, and Functionalization of a Rigid Analogue of Cyclotriveratrylene

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Organomediated Enantioselective ¹⁸F Fluorination for PET Applications

Organomediated Enantioselective ¹⁸F Fluorination for PET Applications

Organomediated Enantioselective ¹⁸F Fluorination for PET Applications