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Pregled bibliografske jedinice broj: 314283

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


Cepanec, Ivica; Litvić, Mladen; Pogorelić, Ivan
Efficient Synthesis of 3-Hydroxy-1, 4-benzodiazepines Oxazepam and Lorazepam by New Acetoxylation Reaction of 3-Position of 1, 4-Benzodiazepine Ring // Organic Process Research & Development, 10 (2006), 6; 1192-1198 doi:10.1021/op068009u (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 314283 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

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

Autori
Cepanec, Ivica ; Litvić, Mladen ; Pogorelić, Ivan

Izvornik
Organic Process Research & Development (1083-6160) 10 (2006), 6; 1192-1198

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
oxazepam; lorazepam; acetoxylation

Sažetak
Simple, efficient, and scalable syntheses of 3-hydroxy-1, 4- benzodiazepines, 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).

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Avatar Url Mladen Litvić (autor)

Avatar Url Ivica Cepanec (autor)

Citiraj ovu publikaciju

Cepanec, Ivica; Litvić, Mladen; Pogorelić, Ivan
Efficient Synthesis of 3-Hydroxy-1, 4-benzodiazepines Oxazepam and Lorazepam by New Acetoxylation Reaction of 3-Position of 1, 4-Benzodiazepine Ring // Organic Process Research & Development, 10 (2006), 6; 1192-1198 doi:10.1021/op068009u (međunarodna recenzija, članak, znanstveni)
Cepanec, I., Litvić, M. & Pogorelić, I. (2006) Efficient Synthesis of 3-Hydroxy-1, 4-benzodiazepines Oxazepam and Lorazepam by New Acetoxylation Reaction of 3-Position of 1, 4-Benzodiazepine Ring. Organic Process Research & Development, 10 (6), 1192-1198 doi:10.1021/op068009u.
@article{article, year = {2006}, pages = {1192-1198}, DOI = {10.1021/op068009u}, keywords = {oxazepam, lorazepam, acetoxylation}, journal = {Organic Process Research and Development}, doi = {10.1021/op068009u}, volume = {10}, number = {6}, issn = {1083-6160}, title = {Efficient Synthesis of 3-Hydroxy-1, 4-benzodiazepines Oxazepam and Lorazepam by New Acetoxylation Reaction of 3-Position of 1, 4-Benzodiazepine Ring}, keyword = {oxazepam, lorazepam, acetoxylation} }
@article{article, year = {2006}, pages = {1192-1198}, DOI = {10.1021/op068009u}, keywords = {oxazepam, lorazepam, acetoxylation}, journal = {Organic Process Research and Development}, doi = {10.1021/op068009u}, volume = {10}, number = {6}, issn = {1083-6160}, title = {Efficient Synthesis of 3-Hydroxy-1, 4-benzodiazepines Oxazepam and Lorazepam by New Acetoxylation Reaction of 3-Position of 1, 4-Benzodiazepine Ring}, keyword = {oxazepam, lorazepam, acetoxylation} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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