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

HRID 1087553Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1087553
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-cdf3f5e29dc343e8a48659fca20bce2b
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05036066

Notizen zur Reaktion

Wird geladen…