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Title: Synthesis and screening of 1, 3, 4-oxadiazinoindolinone and s-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;1,3,4-oxadiazinoindolinone;s-triazole derivatives;pyranobenzopyran;antimicrobial activity
Issue Date: Jul-2005
Publisher: CSIR
IPC Code: Int.Cl.7 C 07 D 311/76
Abstract: 3-Formyl-4- hydroxycoumarin is treated with malonic acid in the presence of zinc chloride catalyst to give 2H, 5H-2,5-dioxo-3-pyrano[3, 2-c]benzopyranoic acids 1a-d which on treatment with methanol in the presence of thionyl chloride give methyl 2H, 5H-2,5-dioxopyrano[3, 2-c]benzopyran-3-oates 2a-d. Compounds 2a-d were converted into their acid hydrazides 3a-d. 3a-d on treatment with isatin yield 1H, 2H-3-(2H, 5H-2,5-dioxopyrano[3, 2-c]benzopyran-3-carboxyhydrazono)-2-indolinones 4a-d which on cyclisation with conc. H2SO4 afford 3-[1, 3, 4-oxadiazino[5, 6-b]indol-2-yl]-2,5-dioxopyrano[3,2-c]benzopyrans 5a-d. Acid hydrazides 3a-d on treatment with carbon disulfide in 10% KOH at room temperature followed by treatment with ortho-chlorobenzoic acid hydrazide furnish 3-(2H, 5H-2, 5-dioxopyrano[3, 2-c]benzopyran-3-yl)-4-{N-2'-chlorophenylcarboxamido]-5-mercapto-1,2,4-triazoles 6a-d.
Page(s): 1465-1469
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.44B(07) [July 2005]

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