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Title: Synthesis and antimicrobial screening of 3<i style="">H</i>,11<i style="">H</i>-9-methyl-3-oxopyrano[2,3-<i style="">f</i>]cinnolino[3,4-<i style="">c</i>]pyrrazole and its derivatives
Authors: Choudhari, Bharati P
Mulwad, Vinata V
Keywords: Aminocoumarin
cinnolino [3,4-<i style="">c</i>]pyrrazoles
antimicrobial activity
Issue Date: Jan-2006
Publisher: CSIR
Series/Report no.: <b>Int</b>.<b>Cl</b>.<b><sup>7</sup> C 07 D // A 61 P 31/04, 31/10</b>
Abstract: The coupling reaction of the diazonium salt solution of the 6-aminocoumarins <b style="">1a-c</b> with ethylacetoacetate has afforded the corresponding hydrazones <b style="">2a-c</b>, which on further intramolecular cyclisation with PPA yielded the corresponding 3<i style="">H</i>,7<i style="">H</i>,10<i style="">H</i>-9-acetyl-3,10-dioxopyrano[2,3-<i style="">f</i>]cinnolines <b style="">3a-c</b>. Reaction of <b style="">3a-c</b> with hydrazine hydrate has afforded the 3<i style="">H</i>,11<i style="">H</i>-9-methyl-3-oxopyrano[2,3-<i style="">f</i>]cinnolino[3,4-<i style="">c</i>]pyrrazoles <b style="">4a-c</b>, which on Mannich condensation with formaldehyde and morpholine yield the corresponding 3<i style="">H</i>-9-methyl-3-oxo-11-(<i style="">N</i>-methylenemorpho­lino)pyrano[2,3-<i style="">f</i>]cinnolino[3,4-<i style="">c</i>] pyrrazoles <b style="">5a-c</b>. The reaction of <b style="">3a-c</b> with phenyl hydrazine and 4-methyl-7-methoxycoumarin-6-ylhydrazine hydrochloride afforded 3<i style="">H</i>-9-methyl-3-oxo-11-phenyl pyrano[2,3-<i style="">f</i>]cinnolino[3,4-<i style="">c</i>]pyrrazoles <b style="">6a-c</b> and 3<i style="">H</i>-9-methyl-3-oxo-11-(4-methyl-7-methoxy-2-oxo-2<i style="">H</i>-[1]-benzo­py­ran-6-yl)pyrano[2,3-<i style="">f</i>]cinnolino[3,4-<i style="">c</i>]pyrrazoles <b style="">7a-c</b>, respectively. The structures of the compounds <b style="">2-7a-c</b> 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.<b style=""> </b>
Description: 309-313
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.45B(01) [January 2006]

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