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-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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Veröffentlicht in:Chemical & pharmaceutical bulletin 1990/11/25, Vol.38(11), pp.3182-3183
Hauptverfasser: NAKAO, Tohru, OBATA, Minoru, KAWAKAMI, Minoru, MARUBAYASHI, Nobuhiro, MORITA, Kenji, TAHARA, Tetsuya
Format: Artikel
Sprache:eng
Schlagworte:
antianxiety
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
lead tetraacetate
Organic chemistry
Preparations and properties
sodium bromite
stereoselective oxidation
sulfide
sulfoxide
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Zusammenfassung: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