Methyl propiolate → methyl 4,5-dihydro-7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylate

HRID 648516Notes

Reaction equation

HRID 648516 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]([O:25][CH3:26])(=[O:24])[C:22]#[CH:23]>C1(C)C=CC=CC=1>[O:2]=[C:3]1[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:23][C:22]([C:21]([O:25][CH3:26])=[O:24])=[C:6]2[N:7]1[CH2:8][CH2:9][C:10]1[CH:14]=[CH:13][S:12][C:11]=12

Participants

4

Reactant 2

HCID 13536Methyl propiolateHCID 147700175,6-Dihydro-3-hydroxy-2-phenylthiazolo[3,2-a]thieno[2,3-c]pyridinium hydroxide

Product 1

HCID 14666687methyl 4,5-dihydro-7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(ba) A suspension of 31.65 g of 5,6-dihydro-3-hydroxy-2-phenylthiazolo[3,2-a]thieno[2,3-c]pyridinium hydroxide (internal salt) in 770 ml of toluene was treated with 10.94 g of methyl propiolate, the mixture was heated under reflux until the reaction has finished, the reaction mixture was evaporated in vacuo and the residue was chromatographed on silica gel with toluene/ethyl acetate (9:1). There was obtained methyl 4,5-dihydro-7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylate as yellow crystals of m.p. 116° (from ethyl acetate).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux until the reaction
  3. customthe reaction mixture was evaporated in vacuo
  4. customthe residue was chromatographed on silica gel with toluene/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-7cba005562b84c2797a3af10e3b52a54
Source dataset
uspto-grants-1988_04
Patent number
US04735940

Reaction notes

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