110421-88-0Relevant articles and documents
Metal-free and fecl3-catalyzed synthesis of azines and 3,5-diphenyl-1H-pyrazole from hydrazones and/or ketones monitored by high resolution ESI+-MS
Lasri, Jamal,Ismail, Ali I.
, p. 362 - 373 (2019/05/21)
9-Fluorenone azine 2a or benzophenone azine 2b have been synthesized, respectively, by treatment of 9-fluorenone hydrazone la or benzophenone hydrazone lb with FeCl3 Lewis acid catalyst in CHCb. Treatment of la and lb with FeCb affords the asymmetrical azine l-(diphenylmethylene)-2-(9H-fluoren-9-ylidene)hydrazine 2c. l,3-Diphenyl-2-propenone 3 reacts with hydrazine to produce l-((E)-l,3-diphenylallylidene)hydrazine 3a. Under prolonged heating, 3a undergoes a cyclization to yield 3,5-diphenyl-lH-pyrazoIe 4. Chalcone 3 reacts with la or lb to produce a mixture of 4 and 2a or 4 and 2b, respectively. The reaction of cyclohexanone 5 with hydrazine leads to the formation of 1,2-dicyclohexylidene hydrazine 6. Ketone 5 reacts with la or lb to give the asymmetrical azine product 6a or 6b, respectively. The progress of the reactions has been monitored by electrospray ionization mass spectrometry (ESI-MS), and the compounds have been characterized by elemental analyses, IR,1H,13C and DEPT-135 NMR spectroscopy and also by high resolution ESI+-MS.
