STEREOSELECTIVE OXIDATION OF 2-(4-CHILOROPHENYL)-4a, 5-DIHYDRO-2H-(1)BENZOTHIOPYRANO[4, 3-c]PYRIDAZIN-3(4H)-ONE TO SULFOXIDE

Stereoselective oxidation of 2-(4-chlorophenyl)-4a, 5-dihydro-2H-(1)benzothiopyrano[4, 3-c]pyridazin-3(4H)-one (1) to sulfoxides with a variety of oxidants was examined under mild conditions. The oxidation with Pb(OAc)4 and NaBrO2 stereoselectively gave the trans-sulfoxide (2) in good yield. The per...

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Published inChemical & pharmaceutical bulletin Vol. 38; no. 11; pp. 3182 - 3183
Main Authors NAKAO, Tohru, OBATA, Minoru, KAWAKAMI, Minoru, MARUBAYASHI, Nobuhiro, MORITA, Kenji, TAHARA, Tetsuya
Format Journal Article
LanguageEnglish
Published TOKYO The Pharmaceutical Society of Japan 1990
Pharmaceutical Soc Japan
Maruzen
Subjects
antianxiety
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
lead tetraacetate
Life Sciences & Biomedicine
Organic chemistry
Pharmacology & Pharmacy
Physical Sciences
Preparations and properties
Science & Technology
sodium bromite
stereoselective oxidation
sulfide
sulfoxide
Stereoselectivity
Sulfur heterocycle
Nitrogen heterocycle
Chlorine Organic compounds
Sulfoxide
Aromatic compound
Oxidation
Tricyclic compound
Biological activity
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Summary:Stereoselective oxidation of 2-(4-chlorophenyl)-4a, 5-dihydro-2H-(1)benzothiopyrano[4, 3-c]pyridazin-3(4H)-one (1) to sulfoxides with a variety of oxidants was examined under mild conditions. The oxidation with Pb(OAc)4 and NaBrO2 stereoselectively gave the trans-sulfoxide (2) in good yield. The peroxy reagents and NaIO4 afforded mostly the cis-isomer (3).
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.38.3182