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Title: Synthesis and screening of 1, 3, 4-oxadiazinoindolinone and <i>s</i>-triazole derivatives of pyranobenzopyran
Authors: Mulwad, V V
Chaskar, A C
Shirodkar, J M
Keywords: 3-Formyl-4-hydroxycoumarin
zinc chloride
benzopyronic acids
thionyl chloide
s-triazole derivatives
antimicrobial activity
Issue Date: Jul-2005
Publisher: CSIR
Series/Report no.: <b>Int</b>.<b>Cl</b>.<b><sup>7</sup> C 07 D 311/76</b>
Abstract: 3-Formyl-4- hydroxycoumarin is treated with malonic acid in the presence of zinc chloride catalyst to give 2<i>H</i>, 5<i>H</i>-2,5-dioxo-3-pyrano[3, 2-<i>c</i>]benzopyranoic acids <b>1a-d </b>which on treatment with methanol in the presence of thionyl chloride give methyl 2<i>H</i>, 5<i>H</i>-2,5-dioxopyrano[3, 2-<i>c</i>]benzopyran-3-oates <b>2a-d</b>. Compounds <b>2a-d </b>were converted into their acid hydrazides <b>3a-d</b>.<b> 3a-d </b>on treatment with isatin yield 1<i>H</i>, 2<i>H</i>-3-(2<i>H</i>, 5<i>H</i>-2,5-dioxopyrano[3, 2-<i>c</i>]benzopyran-3-carboxyhydrazono)-2-indolinones <b>4a-d</b> which on cyclisation with conc. H<sub>2</sub>SO<sub>4</sub> afford 3-[1, 3, 4-oxadiazino[5, 6-<i>b</i>]indol-2-yl]-2,5-dioxopyrano[3,2-c]benzopyrans <b>5a-d</b>. Acid hydrazides <b>3a-d</b> on treatment with carbon disulfide in 10% KOH at room temperature followed by treatment with ortho-chlorobenzoic acid hydrazide furnish 3-(2<i>H</i>, 5<i>H</i>-2, 5-dioxopyrano[3, 2-<i>c</i>]benzopyran-3-yl)-4-{N-2'-chlorophenylcarboxamido]-5-mercapto-1,2,4-triazoles <b>6a-d</b>.
Description: 1465-1469
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.44B(07) [July 2005]

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