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

HRID 477938Notes

Reaction equation

HRID 477938 reaction equation
[OH-].[OH:2][C:3]1[N+:7]2[CH:8]=[CH: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[CH:8]=[CH:9][C:10]1[CH:14]=[CH:13][S:12][C:11]=12

Participants

4

Reactant 2

HCID 13536Methyl propiolateHCID 190204883-Hydroxy-2-phenylthiazolo[3,2-a]thieno[2,3-c]pyridinium hydroxide

Product 1

HCID 14666705methyl 7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(ca) 22.9 g of 3-hydroxy-2-phenylthiazolo[3,2-a]thieno-[2,3-c]pyridinium hydroxide (internal salt) and 13.6 ml of methyl propiolate were heated together under argon in 1000 ml of toluene until the starting material was completely taken up. The solvent was removed in vacuo and the residue was stirred in 500 ml of ether/methanol (9:1) for 1 hour. The yellow crystals obtained were removed by filtration under suction. There was obtained methyl 7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylate of m.p. 153°-154° (dec.). An additional portion of product of m.p. 151°-152° (dec.) can be obtained by chromatography of the filtrate on silica gel.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe yellow crystals obtained
  3. customwere removed by filtration under suction

Sources & evidence

ORD record
ord-49479d7c15e24bc6b5f174dadef2c8b3
Source dataset
uspto-grants-1989_12
Patent number
US04889848

Reaction notes

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