Ueber Phenyl‐ und Pyridylpyrrole und die Constitution des Nicotins

Pyridine alkaloids with activity in the central nervous system

“…21 The chemical structure of nicotine was later established by Pictet and Crépieux through total synthesis in 1895. 22 Nicotine is also present (albeit in lower amounts) in other genera of the Solanaceae family, such as potatoes, tomatoes and green peppers. 19 , 20 Today, N. tabacum is cultivated in over 120 countries worldwide, where it is used to make cigarettes and as the source of nicotine for replacement therapy (NRT).…”

Pharmaceuticals

“…[529,530] Key steps are the formation of 3-(1H-pyrrol-1-yl)-pyridine from 3-aminopyridine and mucic acid and its rearrangement to 3-(1H-pyrrol-2-yl)-pyridine at high temperatures. N-Methylation and sequential reduction give eventually racemic nicotine, which can be separated with tartaric acid into its enantiomers.…”

Tautomerism and rotamerism in 2‐methylamino‐, 2‐anilino‐, 2‐acetamido‐, and 2‐benzamido‐pyridines

“…The Angyalsl have determined the equilibrium constant, KT, of the tautomeric reaction I 2 I 1 in solution at 25oC as equal to 2x105 showing in this manner that the amino tautomer strongly prevails. The analysis of the 14N NMR spectra of aminopyridines has lead Stefaniak2 to the conclusion that the acetone solution of 2-aminopyridine contains 89% of form (I) and 11% of form (11).…”

“…2-Acylamino derivatives of pyridine, 2-acetamido-and 2-benzamido-pyridines, showed very specific and unexpected UV absorption. Their longwave bands at 275 and 276 nm, respectively, speak against 1 H-2-pyridineimine structure (11). They belong to the absorptions within the pure 2-pyridineamine system (I).…”