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Title: An efficient synthesis of quinalone-3-(N-phenylpyrazoles) and quinalone-3-cyclohexadienone derivatives
Authors: Darsi, S S Praveen Kumar
Kumar, K Shiva
Devi, B Rama
Naidu, A
Dubey, P K
Keywords: 2-Chloroquinoline-3-carboxaldehyde;3-formyl-2(1H)-quinalone;Phenylhydrazine;Acetoaceta¬nilide;Chloranil
Issue Date: Aug-2013
Publisher: NISCAIR-CSIR, India
Abstract: An efficient synthesis of quinalone-3-(N-phenylpyrazoles) 5 and quinalone-3-(cyclohexadienones) 8 has been described. 2-Chloroquinoline-3-carboxaldehyde 1, on reaction with 4N HCl gives 3-formyl-2(1H)-quinalone 2. The latter is reacted with acetophenone in the presence of NaOH as base to yield the corresponding quinalone-3-chalcone 3 which on treatment with phenylhydrazine gives 3-(dihydropyrazolo)quinolone 4. Dehydrogenation of 4 with chloranil yields the corresponding 5. Compound 3 on bromination yields the dibromo derivative 6 which on treatment with phenylhydrazine directly yields 5. On the other hand, 3 on treatment with acetoacetanilide in methanol using acetic acid as a catalyst affords the corresponding quinalone-3-(cyclohexenone) derivatives 7 which on dehydrogenation with chloranil, affords the corresponding 8 in excellent yield.
Page(s): 1146-1151
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.52B(08) [August 2013]

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