The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of furan amines and their catalytic conversion into five-membered nitrogenous heterocycles》. Authors are Shuikin, N. I.; Petrov, A. D.; Glukhovtsev, V. G.; Bel’skii, I. F.; Skobtsova, G. E..The article about the compound:3-Methyl-1H-pyrrolecas:616-43-3,SMILESS:CC1=CNC=C1).Name: 3-Methyl-1H-pyrrole. Through the article, more information about this compound (cas:616-43-3) is conveyed.
CH2:CHCHO added to sylvan in AcOH in the presence of hydroquinone at 40° gave after 2 hrs. 65% 2-methyl-5-(3-oxopropyl)furan, b4 58°, n20D 1.4762, d20 1.0360; with 50% H2SO4 as a catalyst, the yield was 43%. The latter catalyst with crotonaldehyde similarly gave 53% 2-methyl-5-(1-methyl-3-oxopropyl)furan, b3 67°, 1.4730, 1.0093, while mesityl oxide gave 75% 2-methyl-5-(1,1-dimethyl-3-oxobutyl)furan, b2 61°, 1.4700, 0.9747. These carbonyl derivatives were hydrogenated in MeOH saturated with NH3 over Raney Ni at 100-50 atm. and 80° and gave: 2-methyl-5-(3-aminopropyl)-furan, b6 82°, 1.4840, 0.9758; 2-methyl-5-(1-methyl-3-amino-propyl)furan, b7 85°, 1.4800, 0.9591; 2-methyl-5-(1,1-dimethyl-3-aminobutyl)furan, b4 75°, 1.4741, 0.9365. The latter was hydrogenated at 250° over 15% Pt-asbestos to 2,4,4-trimethyl-5-butylpyrrolidine, b5 39°, 1.4444, 0.8319. Raman spectra of the products were reported.
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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