3 research outputs found
Chemoselective reactions of 3,6-diacetylindoles towards araldehydes, hydrazine hydrate and bromine: Synthesis and antimicrobial activity of novel 6-pyridyl/6-hydrazinoacetyl/6-bromoacetyl-3-acetylindole derivatives
1137-114
<span style="font-size:20.5pt;mso-bidi-font-size:14.5pt; font-family:"Times New Roman";mso-fareast-font-family:"Times New Roman"; mso-ansi-language:EN-US;mso-fareast-language:EN-US;mso-bidi-language:AR-SA">Synthesis and antimicrobial activity of novel 4<i style="mso-bidi-font-style:normal">H</i>-pyrano[2,3-<i style="mso-bidi-font-style:normal">f</i>]indole derivatives<sup>†</sup></span>
178-1825-Hydroxyindoles 1a-b have been subjected to
regioselective Friedel-Craft 's acetylation to secure 3,6-diacetyl-5- hydroxyindoles
2a-b which on condensation with
benzoic acids by using pyridine and phosphorous oxychloride furnish the required
esters 3a-f in good yields. These
esters 3a-f are subjected to
Baker-Venkataraman transfomlations to obtain 3-
acetyl-6-benzoylacetyl-5-hydroxyindoles
4a-f which are refluxed in AcOH and
conc. HCI to afford the novel 2-phenyl-4H-pyrano[
2,3-f]indol-4-one
derivatives 5a-f. Similarly when 4a-f are heated with Ac2O and A<i style="mso-bidi-font-style:
normal">cONa new 2-methyl-3-benzoyl-4H-pyrano[2,3-f]indol-4-one
derivatives 6a-f are obtained. All
these new compounds have been screened for their antibacterial and antifungal
activities.</span
Synthesis and antimicrobial activity of novel 5-tetrazolyl/oxadiazolyl/benzimidazolylmethoxyindole derivatives
188-1911-Alkyl-3-acetyl-2-methylindol-5-yloxyacetonitriles
2a,b, prepared by reacting
5-hydroxyindoles 1a,b with chloroacetonitrile
have been converted to 1,2,3,4-tetrazolylindoles <b style="mso-bidi-font-weight:
normal">3a,b using NaN3. <span style="font-size:14.0pt;
mso-bidi-font-size:8.0pt">LiCI and NH<span style="mso-bidi-font-size:
6.0pt">4C1
in dry
dimethylformamide. Conversion
of tetrazolylindoles 3a,b into 1,3,4-oxadiazolylindoles
4a,b has been achieved by heating
with acetic anhydride. Hydrolysis of 1-alkyl-3-ethoxycarbonyl-5-ethoxycarbonylmethoxy-2-methylindoles
5a,b with ethanolic NaOH gives the
corresponding diacids 6a,b, which on
heating with o-phenylenediamine in 6N HCI undergo condensation with
concomitant decarboxylation to yield the 1-alkyl-5-(benzimidazol-2-ylmethoxy)-2-
methylindoles 7a,b. The newly
synthesised bisheterocycles have been screened for their antibacterial and
antifungal
activities.</span