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Title: Synthesis and antimicrobial screening of 3H,11H-9-methyl-3-oxopyrano[2,3-f]cinnolino[3,4-c]pyrrazole and its derivatives
Authors: Choudhari, Bharati P
Mulwad, Vinata V
Keywords: Aminocoumarin;coupling;cyclisation;cinnolino [3,4-c]pyrrazoles;antimicrobial activity
Issue Date: Jan-2006
Publisher: CSIR
IPC Code: Int.Cl.7 C 07 D // A 61 P 31/04, 31/10
Abstract: The coupling reaction of the diazonium salt solution of the 6-aminocoumarins 1a-c with ethylacetoacetate has afforded the corresponding hydrazones 2a-c, which on further intramolecular cyclisation with PPA yielded the corresponding 3H,7H,10H-9-acetyl-3,10-dioxopyrano[2,3-f]cinnolines 3a-c. Reaction of 3a-c with hydrazine hydrate has afforded the 3H,11H-9-methyl-3-oxopyrano[2,3-f]cinnolino[3,4-c]pyrrazoles 4a-c, which on Mannich condensation with formaldehyde and morpholine yield the corresponding 3H-9-methyl-3-oxo-11-(N-methylenemorpho­lino)pyrano[2,3-f]cinnolino[3,4-c] pyrrazoles 5a-c. The reaction of 3a-c with phenyl hydrazine and 4-methyl-7-methoxycoumarin-6-ylhydrazine hydrochloride afforded 3H-9-methyl-3-oxo-11-phenyl pyrano[2,3-f]cinnolino[3,4-c]pyrrazoles 6a-c and 3H-9-methyl-3-oxo-11-(4-methyl-7-methoxy-2-oxo-2H-[1]-benzo­py­ran-6-yl)pyrano[2,3-f]cinnolino[3,4-c]pyrrazoles 7a-c, respectively. The structures of the compounds 2-7a-c have been established on the basis of spectral and analytical data. All the above compounds have been screened for their antimicrobial activities and are found to possess significant antibacterial and antifungal activities.
Page(s): 309-313
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.45B(01) [January 2006]

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