1011416-46-8Relevant articles and documents
A novel synthesis of 4-pyridazineacetic acids via ring expansion of N-cyanomethylated 3-pyrazoline-4-acetic acids
Masumoto, Eiichi,Maruoka, Hiroshi,Okabe, Fumi,Nishida, Sho,Tomita, Ryoko,Fujioka, Toshihiro,Yamagata, Kenji
, p. 893 - 899 (2012/11/07)
A novel synthetic route to 4-pyridazineacetic acids 10-12 has been achieved by the ring-expansion reaction of N-cyanomethylated 3-pyrazoline-4-acetic acids 7-9. 1H-Pyrazole-4-acetic acids 1-3 were reacted with iodoacetonitrile in the presence of triethylamine in refluxing acetonitrile to give the corresponding C-cyanomethylated 1H-pyrazole-4-acetic acids 4-6 as major products together with N-cyanomethylated 3-pyrazoline-4-acetic acids 7 and 8 as minor products. On the other hand, reactions of 1 and 3 with chloroacetonitrile in the presence of triethylamine in refluxing chloroform afforded the corresponding N-cyanomethylated 3-pyrazoline-4-acetic acids 7 and 9 as major products. Thermal treatment of 7-9 with sodium hydride in N,N-dimethylformamide caused ring expansion to yield the corresponding 4-pyridazineacetic acids 10-12.