36758-69-7Relevant articles and documents
Photochemistry of Phenyl-Substituted 1-Methylpyrazoles
Pavlik, James W.,Kebede, Naod
, p. 8325 - 8334 (2007/10/03)
Direct irradiation of 1-methyl-4-phenylpyrazole (2) in methanol results in regiospecific phototransposition to 1-methyl-4-phenylimidazole (4) and in photocleavage to (E)/(Z)-3-(N-methylamino)-2-phenylpropenenitrile (5) and (E)/(Z)-2-(N-methylaimno)-1-phenylethenyl isocyanide (6). Deuterium labeling confirms that the phototransposition occurs via the P4 permutation pathway. Separate experiments show that 5 and 6 undergo (Z) → (E) isomerization and photocyclization to imidazole 4. Quantum yields for these reactions show that the sequence 2 → 6 → 4 is a major pathway for the P4 phototransposition of 2 → 4. Isocyanides were also detected as intermediates in the P4 phototransposition of a variety of other pyrazoles confirming the generality of this pathway in pyrazole photochemistry. Direct irradiation of 1-methyl-5-phenylpyrazole (3) resulted in the formation of 1-methyl-5-phenylimidazole (7), 1-methyl-2-phenylimidazole (8), and 1-methyl-4-phenylimidazole (4). Deuterium labeling revealed that these products were formed by P4, P6, and P7 permutation pathways, respectively. (E)/(Z)-3-(N-methylamino)-3-phenylpropenenitrile (9) and (E)/(Z)-2-(N-methylamino)-2-phenylethenyl isocyanide (10) photocleavage products were also formed in this reaction. Irradiation of 3 in furan solvent did not result in phototransposition but led to the formation of endo and exo adducts formed by Diels-Alder reaction of furan with 4-phenyl-5-methyl-1,5-diazabicyclo[2.1.0]pent-2-ene. This constitutes the first direct evidence for the formation of a 1,5-diazabicyclo[2.1.0]hex-2-ene from photolysis of a pyrazole and is consistent with the electrocyclic ring closure - heteroatom migration mechanism suggested for the P6 and P7 phototranspositions.
β Aminocinnamonitriles as potential antiinflammatory agents
Lang Jr.,Cohen
, p. 441 - 443 (2007/10/08)
A number of β aminocinnamonitriles have been prepared by the reaction of salts of acetonitrile and proprionitrile with benzonitrile. These materials were evaluated in the carrageenan antiinflammatory screen in Royal Hart, Wistar strain rats. Despite food weight gains with the parent molecule, β aminocinnamonitrile, only marginal activity was found in related compounds and some possible 'metabolites'.
