3-Onium derivatives of 1,4-benzodiazepin-2-ones with tertiary organic bases

KOVAC, T.; Kajfež, F.; Šunjić, Vitomir; Oklobdzija, M.

doi:10.1021/jm00253a028

Cited by 10 publications

(3 citation statements)

References 1 publication

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“…The synthesis of 3-acetoxy-1,4-benzodiazepines 7 and 8 by direct acetoxylation of 1,4-benzodiazepines 3 and 4 with lead(IV) acetate and potassium iodide in acetic acid is known from the literature . Despite the fact that this process proceeds cleanly and effectively, the use of lead-containing reagent is completely unacceptable for industrial production of APIs.…”

Section: Resultsmentioning

confidence: 99%

Efficient Synthesis of 3-Hydroxy-1,4-benzodiazepines Oxazepam and Lorazepam by New Acetoxylation Reaction of 3-Position of 1,4-Benzodiazepine Ring

Cepanec¹,

Litvić²,

Pogorelić³

2006

Org. Process Res. Dev.

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Simple, efficient, and scalable syntheses of 3-hydroxy-1,4benzodiazepines, oxazepam (1), and lorazepam (2) were developed. The syntheses are based on the new acetoxylation reaction of the 3-position of the 1,4-benzodiazepine ring. The reaction involves iodine (20-50 mol %)-catalyzed acetoxylation in the presence of potassium acetate (2 equiv) and potassium peroxydisulfate (1-2 equiv) as a stoichiometric oxidant affording the corresponding 3-acetoxy-1,4-benzodiazepines in good-to-high yields. The latter were converted by selective saponification to 3-hydroxy-1,4-benzodiazepines of very high purity (>99.8%) in an overall yield of 83% (oxazepam) and 64% (lorazepam).

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Section: Resultsmentioning

confidence: 99%

Efficient Synthesis of 3-Hydroxy-1,4-benzodiazepines Oxazepam and Lorazepam by New Acetoxylation Reaction of 3-Position of 1,4-Benzodiazepine Ring

Cepanec¹,

Litvić²,

Pogorelić³

2006

Org. Process Res. Dev.

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“…Alternatively, the crude residues were dissolved in the most polar solvent of the system indicated in Table I, and crystallization was induced in the chilled solution by addition of a less polar solvent. Characteristic data for compounds [7][8][9][10][11][12][13][14][15] are presented in Table I.…”

Section: Methodsmentioning

confidence: 99%

“…The slower moving zone gave 7.3 g of pure 19 (epimeric structure); an analytical sample was obtained as with compound 18: IR (KBr) 3240, 1750, 1715, 1690, 1612, 1480, 1225, 850 (aanomeric C-C), 735, 705 cm"1; NMR (CDClg) ~2.0 (s, 4 X COCH3), 3.7-5.2 (m, 11 H, including -anomeric C^H), 7.2-7.8 (m, 9 ), 10.4 (s, 1 H). Anal.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of some carbon-3 substituted 1,4-benzodiazepin-2-ones and their central effects

KOVAC¹,

Kajfež²,

Šunjić³

et al. 1979

J. Med. Chem.

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Starting from 3-hydroxy-1,4-benzodiazepin-2-ones 1--3, via 3-chloro derivatives 4--6, 13 new C(3)-substituted 1,4-benzodiazepin-2-ones were synthesized. Reaction of 4--6 with ethylene glycol yielded 3-(beta-hydroxyethyl) derivatives 7--9. Similar reaction with the isopropylidene derivative of glycerol afforded 10--12, which on hydrolysis of the isopropylidene group hielded glycerol derivatives 13--15. Reaction of trichloroacetyl chloride with oxazepam and temazepam yielded the corresponding trichloroacetyl esters 16 and 17. The beta-hydroxyethyl derivative 7 was conjugated with an acetylated glucopyranose derivative to give isomeric 18 and 19. Partition coefficients (log Poct) and central nervous system activities (in six stranded tests) were determined for 7--15 as well as several standard compounds. Most of the compounds exhibiting beneficial central nervous system activity had Poct values between 1.71 and 2.48. No correlation between lipophilicity and central nervous system activity could be discerned for these compounds.

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Dihydro‐1,4‐Benzodiazepinones and Thiones

Walser

Fryer

1991

Chemistry of Heterocyclic Compounds: A Series of Monographs

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3-Onium derivatives of 1,4-benzodiazepin-2-ones with tertiary organic bases

Cited by 10 publications

References 1 publication

Efficient Synthesis of 3-Hydroxy-1,4-benzodiazepines Oxazepam and Lorazepam by New Acetoxylation Reaction of 3-Position of 1,4-Benzodiazepine Ring

Efficient Synthesis of 3-Hydroxy-1,4-benzodiazepines Oxazepam and Lorazepam by New Acetoxylation Reaction of 3-Position of 1,4-Benzodiazepine Ring

Synthesis of some carbon-3 substituted 1,4-benzodiazepin-2-ones and their central effects

Dihydro‐1,4‐Benzodiazepinones and Thiones

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