The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of α,α’-unsubstituted pyrroles》. Authors are Plieninger, H.; Buhler, W..The article about the compound:3-Methyl-1H-pyrrolecas:616-43-3,SMILESS:CC1=CNC=C1).Product Details of 616-43-3. Through the article, more information about this compound (cas:616-43-3) is conveyed.
α,α’-Unsubstituted pyrroles were made as intermediates for the synthesis of porphyrins and bile pigments. 3-Methylpyrrole (I) and 3,4-dimethylpyrrole were obtained in 40% yield (based on the starting acetal) from MeCOCH2CH(OMe)2 (II) and MeCOCHMeCH(OMe)2, resp. II cyanohydrin was condensed with dihydropyrene (III) to give MeC(CN)(OCH.CH2.CH2.CH2.CH2.O)CH2CH(OMe)2 which was reduced to the corresponding amine with LiAlH4. Acidification liberated the pyrrole but because of further transformation in the presence of acid, it could not be isolated. Acetylation of the amine, followed by treatment with MeC6H4SO3H in absolute Me2CO, split off III, liberated the aldehyde group and gave I acetyl derivative in one step. I was obtained by careful alk. hydrolysis.
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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate