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Amidine‐Induced Ring Transformation of a Substituted 1,1‐Dioxo‐1,2‐thiazine‐4‐carbaldehyde into New Pyrimidine Derivatives
Author(s) -
Fanghänel Egon,
Bartossek Hagen,
Baumeister Ute,
Hartung Helmut
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719971230
Subject(s) - amidine , chemistry , thiazine , pyrimidine , ring (chemistry) , transformation (genetics) , hydrolysis , derivative (finance) , medicinal chemistry , stereochemistry , organic chemistry , financial economics , economics , biochemistry , gene
As a masked 1,3‐dicarbonyl compound, the 1,1‐dioxo‐ 2H ‐1,2‐thiazine‐4‐carbaldehyde 1 undergoes ring transformation with amidines to produce 2‐substituted 4‐methyl‐5‐[1‐methyl‐2‐methylthio‐2‐( N ‐phenylsulfamoyl)vinyl]pyrimidines 3a–f . For 3b , an X‐ray structure analysis is reported. From the 4‐methyl‐2‐methylthio‐5‐[1‐methyl‐2‐methylthio‐2‐( N ‐phenylsulfamoyl)vinyl]pyrimidine ( 3e ), the substituted pyrimidinone 4 is obtained by acidic hydrolysis.