1551-09-3Relevant academic research and scientific papers
Synthesis of New 3-Substituted Pyrroles
Stefan, Klaus-Peter,Schuhmann, Wolfgang,Parlar, Harun,Korte, Friedhelm
, p. 169 - 174 (2007/10/02)
The synthesis of 3-alkyl- (4), 3-(ω-bromoalkyl)- (5), 3-iodo- (6), 3-formyl- (9a), 3-acetyl-1-(triisopropylsilyl)pyrrole (9b), of 2--2-propanol (7), 1-(triisopropylsilyl)-3-pyrrolecarboxylic acid (8), and 7-heptanoic acid (10) as well as the desilylation of these products to the corresponding 3-substituted pyrroles 11 is described.Intermediates in these syntheses are 1-(triisopropylsilyl)pyrrole (1), 3-bromo- (2), and 3-lithio-1-(triisopropylsilyl)pyrrole (3). - Keywords: Pyrroles, substituted in position 3 / 1-(Triisopropylsilyl)pyrroles, substituted in position 3
Synthesis of 2-Alkylputrescines from 3-Alkylpyrroles
Garrido, Daniel O. A.,Buldain, Graciela,Ojea, Maria I.,Frydman, Benjamin
, p. 403 - 407 (2007/10/02)
Acylation of 2-(trichloroacetyl)pyrrole gave the 4-acyl derivatives (from 4-formyl to 4-hexanoyl) in good yields.Alkaline treatment gave corresponding 4-acyl-2-pyrrolecarboxylic acids, were decarboxylated to the 3-acylpyrroles by prior conversion to the 3-acyl-2,4,5-triiodopyrroles followed by hydrogenolysis.The 3-acylpyrroles were reduced by treatment with hydrazine in alkaline medium to the 3-alkylpyrroles.The latter were ring-opened by treatment with hydroxylamine in the presence of bicarbonate to give the dioximes of the corresponding 2-alkylsuccinaldehydes, which were then reduced to the 2-alkylpurescines (1,4-diaminobutanes).Ring-opening of 2,3-dimethylpyrrole followed by reduction of the dioxime gave 1,2-dimethylputrescine; the same sequence gave 1,3-dimethylputrescine from 2,4-dimethylpyrrole, while 3,4-dimethylpyrrole did not ring-open and gave the dioxime of 3,4-dimethylmaleimide.
