1-Methyl-1H-pyrrole-2-carbaldehyde → 4H,5H-thieno(3,2-c)pyridin-4-one

HRID 653408

Reaktionsgleichung

Reaktionsgleichung von HRID 653408
C[N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH:7]=[O:8].[S:9]1C=C[C:11](C=O)=[CH:10]1>>[O:8]=[C:7]1[C:3]2[CH:11]=[CH:10][S:9][C:4]=2[CH:5]=[CH:6][NH:2]1

Komponenten

3

Edukt 2

HCID 145041-Methyl-1H-pyrrole-2-carbaldehydeHCID 681353-Thiophenecarboxaldehyde

Produkt 1

HCID 2885254H,5H-thieno(3,2-c)pyridin-4-one

Versuchsvorschrift

The synthesis of this compound was accomplished with the same sequence of reactions as used to prepare IIIc, except that the starting material (X) is 3-thiophenecarboxaldehyde. The multiple step preparation of the positional isomer IIIc' was complicated, however, in that the Curtius-type rearrangement reaction (Example 4) gave the desired VI intermediate compound in low yield as the major product of this reaction was a sym-triazine by-product which resulted from trimerization of the isocyanate intermediate. Nonetheless, application of the reactions outlined in Scheme 1 resulted in production of the IIIc' product, which was a brown gum and was used without further purification.

Aufarbeitung

  1. customThe synthesis of this compound
  2. customto prepare IIIc
  3. customThe multiple step preparation of the positional isomer IIIc'
  4. customhowever, in that the Curtius-type rearrangement reaction (Example 4)

Quellen und Nachweise

ORD-Eintrag
ord-101189d0684e43c88b584ae195334b9b
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04677104

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