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Title: 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
Authors: Lasri, Jamal
Ismail, Ali I
Keywords: Hydrazones;Ketones;Azines;3,5-diphenyl-1H-pyrazole;FeCl3 Lewis acid catalyst;ESI+-MS
Issue Date: Mar-2018
Publisher: NISCAIR-CSIR, India
Abstract: 9-Fluorenone azine 2a or benzophenone azine 2b have been synthesized, respectively, by treatment of 9-fluorenone hydrazone 1a or benzophenone hydrazone 1b with FeCl3 Lewis acid catalyst in CHCl3. Treatment of 1a and 1b with FeCl3 affords the asymmetrical azine 1-(diphenylmethylene)-2-(9H-fluoren-9-ylidene)hydrazine 2c. 1,3-Diphenyl-2-propenone 3 reacts with hydrazine to produce 1-((E)-1,3-diphenylallylidene)hydrazine 3a. Under prolonged heating, 3a undergoes a cyclization to yield 3,5-diphenyl-1H-pyrazole 4. Chalcone 3 reacts with 1a or 1b 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 1a or 1b 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.
Page(s): 362-373
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.57B(03) [March 2018]

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