3. Polycyclic aromatic hydrocarbons. Part XXI

Badger, G. M.; Cook, J. W.; Goulden, F.

doi:10.1039/jr9400000016

Cited by 7 publications

(6 citation statements)

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“…Furthermore, the purified product probably was contaminated with a trace of the more sparingly soluble 1-acenaphthoic acid, for the melting point was not quite as high as that of (5) Arndt and Eistert .5rr , 68, 203 (1935). Two routes were explored for the conversion of this ketone into 1-acenaphthylacetic acid (VII), the first being via the acid chloride and diazo ketone by the Arndt-Eistert p r~c e d u r e .~ While the over-all yield of 50% is adequate, the process is time-consuming and not well adapted to the preparation of a quantity of the acetic acid derivative.…”

Section: -Cholanthroic Acidmentioning

confidence: 99%

7-Cholanthroic Acid

Fieser¹,

Kilmer²

1940

J. Am. Chem. Soc.

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Section: -Cholanthroic Acidmentioning

confidence: 99%

7-Cholanthroic Acid

Fieser¹,

Kilmer²

1940

J. Am. Chem. Soc.

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“…The starting compound for the preparation of 3-(2,3dimethylphenyl)butan-2-one (7) was commercially available 2,3-dimethylphenyl bromide (11), which could also be obtained from 2,3-dimethylaniline (13). 19 2-(1-Bromoethyl)-2-methyl-1,3-dioxolane (14) was synthesized according to the standard procedure, 20 which included the reaction of 3-bromo-2butanone (15) with ethylene glycol in the presence of catalytic amounts of para-toluene sulfonic acid monohydrate and simultaneous azeotropic removal of water formed during the reaction. The Grignard reagent 10 was obtained by the direct reaction of 2,3-dimethylbromobenzene (11) with magnesium metal in dry tetrahydrofuran (THF) keeping the temperature below 50 °C (optimally 48−50 °C).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Commercially Viable Synthesis of Medetomidine Using a Classical Approach to the Imidazole Ring Formation

Orekhov¹

2022

Org. Process Res. Dev.

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A commercially viable and efficient method for the synthesis of medetomidine hydrochloride (1) was developed combining two reliable synthetic approaches: the modern method for C–C bond formation through the sp2–sp3 Kumada cross-coupling and the classical method for the imidazole ring formation based on the Weidenhagen reaction. The latter was earlier limited by the high toxicity of hydrogen sulfide used to recover imidazoles from the copper complexes and difficulties in working up the reaction mixture. We achieved a remarkable advance in the Weidenhagen reaction through the use of nonhazardous complexons providing less than a 10 ppm residual level of metals in the final product. In the developed method, 3-(2,3-dimethylphenyl)butan-2-one (7) is synthesized in a one-step and one-pot manner by the cross-coupling of 2-(1-bromoethyl)-2-methyl-1,3-dioxolane (14) and 2,3-dimethylphenyl magnesium bromide (10), followed by one-pot deprotection of the resulting ethylene ketal 8, and several intermediates at the next steps can be used without additional purification; these benefits enable medetomidine hydrochloride (1) to potentially be produced on a multikilogram scale.

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“…d Since the ICso of the other diastereomer was >100 µ , we suppose that the absolute configuration of the carbon atom in position 9b is OR).e The mixtures of diastereomers were separated by RP HPLC. 39 [al^p = +261.1°( CHClg). t The mixtures of diastereomers were separated by chromatography on cellulose triacetate.…”

Section: Chemistrymentioning

confidence: 99%

Selective non-nucleoside HIV-1 reverse transcriptase inhibitors. New 2,3-dihydrothiazolo[2,3-a]isoindol-5(9bH)-ones and related compounds with anti-HIV-1 activity

Mertens¹,

Zilch²,

König³

et al. 1993

J. Med. Chem.

200

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A series of substituted 2,3-dihydrothiazolo[2,3-a]isoindol-5(9bH)-ones and related compounds 1-73 were synthesized and evaluated for their ability to inhibit reverse transcriptase (RT) of the human immune deficiency virus 1 (HIV-1) and replication of HIV-1 in MT2 cells. The antiviral activity of these compounds depends on the stereoselective configuration of the substituent in position 9b. Structure-activity studies were done within these series of compounds to determine the optimum substituents for antiviral activity. The most potent inhibitors were found in the class of 2,3-dihydrothiazolo[2,3-a]isoindol-5(9bH)-ones bearing a phenyl ring system in position 9b optionally substituted with one or two methyl groups or a chlorine atom in position 8. The most active analogues (R)-(+)-1, (R)-(+)-6, (R)-(+)-13, (R)-(+)-26, and (R)-(+)-53 inhibit the HIV-1 RT with an IC50 between 16 and 300 nM and an IC50 between 10 and 392 nM in MT2 cells, respectively.

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3. Polycyclic aromatic hydrocarbons. Part XXI

Cited by 7 publications

References 0 publications

7-Cholanthroic Acid

7-Cholanthroic Acid

Commercially Viable Synthesis of Medetomidine Using a Classical Approach to the Imidazole Ring Formation

Selective non-nucleoside HIV-1 reverse transcriptase inhibitors. New 2,3-dihydrothiazolo[2,3-a]isoindol-5(9bH)-ones and related compounds with anti-HIV-1 activity

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