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

HRID 477923Notes

Reaction equation

HRID 477923 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-699c15c15227458eabd62dae751458c4
Source dataset
uspto-grants-1989_12
Patent number
US04889848

Reaction notes

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