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

HRID 648528Notes

Reaction equation

HRID 648528 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-08d412d7a15f4705b1661719cd2c110a
Source dataset
uspto-grants-1988_04
Patent number
US04735940

Reaction notes

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