Phenyl vinyl sulphoxide → 4,5-dihydro-8-phenyl-7H-thieno[2,3-a]quinolizin-7-one

HRID 1087536Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1087536
[OH-].[OH:2][C:3]1[N+:7]2[CH2:8][CH2:9][C:10]3[CH:14]=[CH:13][S:12][C:11]=3[C:6]=2S[C:4]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:21]1(S(C=C)=O)C=CC=C[CH:22]=1>C1(C)C(C)=CC=CC=1>[C:15]1([C:4]2[C:3](=[O:2])[N:7]3[C:6](=[CH:21][CH:22]=2)[C:11]2[S:12][CH:13]=[CH:14][C:10]=2[CH2:9][CH2:8]3)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

4

Edukt 2

HCID 88544Phenyl vinyl sulphoxideHCID 147700175,6-Dihydro-3-hydroxy-2-phenylthiazolo[3,2-a]thieno[2,3-c]pyridinium hydroxide

Produkt 1

HCID 147700304,5-dihydro-8-phenyl-7H-thieno[2,3-a]quinolizin-7-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

2.85 g of 5,6-dihydro-3-hydroxy-2-phenylthiazolo[3,2-a]thieno[2,3-c]pyridinium hydroxide (internal salt) was heated under reflux overnight in 100 ml of xylene together with 1.45 ml of phenylvinyl sulfoxide, whereupon the reaction mixture was evaPorated in vacuo and the residue obtained was chromatographed on silica gel with toluene/ethyl acetate (9:1). There was obtained 4,5-dihydro-8-phenyl-7H-thieno[2,3-a]quinolizin-7-one of m.p. 133°-134° (from ethyl acetate).

Aufarbeitung

  1. customwas evaPorated in vacuo
  2. customthe residue obtained
  3. customwas chromatographed on silica gel with toluene/ethyl acetate (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-69a860f6280c4b3c9bbc209d37068482
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05036066

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