13 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
Chemoselectivity of bisindole tetracarboxylate towards hydrazine hydrate:Synthesis and antimicrobial activity of diethyl 5,5'-bis(2,5-dimethylpyrrol-1-ylaminocarbonylmethoxy)-2,2' -dimethyl-1, l' -(ethane-1,2-diyl)di(1<i>H</i>-indole )-3,3'-dicarboxylate
31-35Diethyl 5,5' -dihydroxy-2,2'-dimethyl-1,1'
-(ethane-1,2-diyl)di(1H-indole)-3,3'-dicarboxylate 3 has been prepared in
one-flask procedure by the condensation of diethyl 3,3'-(ethane-2,2' -diyldiimino
)butenoate 1 with 1,4-benzoquinone 2 in 1:2 molar ratio. Reaction
of 3 separately with methyliodide and ethyl chloroacetate affords the corresponding
O-alkylated derivatives 4 and 5, respectively. Exclusive
formation of diethyl 5,5'-bi-(hydrazinocarbonylmethoxy)-2,2' -dimethyl-1,1'(ethane-1,2-diyl)di(1H-indole)-3,3'-dicarboxylate
6 from 5 reveals the chemoselectivity of 5,5'-ester function towards
nucleophilic attack of hydrazine hydrate. This dicarbohydrazide 6 on reacting
with acetonylacetone furnishes diethyl 5,5-'bis(2,5-dimethylpyrrol-l-ylamino-carbonylmethoxy)-2,2'
-dimethyl-1,1'-(ethane-1,2-diyl)di(1H-indo le)-3,3'-dicarboxylate 8.Conformations
of all these bisindole derivatives have been established. Compounds 3, 4, 5,
6 and 8 have also been screened for their antibacterial and antifungal
activities
Some electrophilic substitution reactions on 1-substituted-3-acetyl/carbethoxy-5-hydroxy-2-methylindole and the antimicrobial activity of these new indole derivatives
1679-1685Aminomethylation under Mannich reaction
conditions on 3-carbethoxy-1-furfuryl-5-hydroxy-2-methylindole 1 and the corresponding bromo
derivative 3 occurs regioselectively
at C4 position to furnish the 4-isogramines 2a-d/4a-d. Nitration of
3-carbethoxy/acetyl-1-furfuryl-5-hydroxy-2-methylindoles 1/8 with hydrated ferric nitrate produces 3-carbethoxy/acetyl-
4, 6-dinitro-1-furfuryl-5-hydroxy-2-methylindoles 6/9. Nitration of 4-isograamine 2 and bromoindole 3
involves ipso-substitution and furnish the 4, 6-dinitroindole derivative 6 and not the expected
6-nitro-4-isogramine 5/6-bromo-4-nitroindole
7. However, nitration of
3.6-diacetylindoles 18a-d and
triacetylindole 10 yields
4-nitroindole derivatives
19a-d/11 wherein the acetyl group
remain intact without involving in any ipso-substitution. Acetylation under
Friedel-Crafts reaction conditions on 3-acetyl-1-furfuryl-5-hydroxy
-2-methylindole 8 occurs at both C6-position
of indole and C5-position of furan to furnish the triacetylindole 10. Bromination of 1 with bromine in acetic acid or bromine in dioxane produces only
6-bromoindole 3. The structures of
all these newly synthesised compounds are confirmed by their spectral and
analytical data and all these compounds are screened for antimicrobial
activity
Chemoselective reaction of bisheterocycle dicarboxylate towards hydrazine hydrate: Synthesis and antimicrobial activity of some new trisheterocycles:5-Pyrrolylaminocarbonyl/ oxadiazolyl/mercaptooxadiazolylmethoxy-1-furfuryl-2-methylindoles
3108-3112Chemoselectivity of C5-ester over
C3-carbethoxy ester function of the bisheterocycle dicarboxylate towards
the nucleophilic attack of hydrazine hydrate has been evidenced by the exclusive
formation of 1-furfuryl-3-carbethoxy-5-hydroxy-2-methylindol-5-yloxyacetic acid
hydrazide which is reacted separately with acetonyl acetone, triethyl orthoformate,
carbon
disulphide and boiling ethanolic potassium
hydroxide to furnish respectively the 1-furfuryl-3-carbethoxy-5-(2, 5-dimethylpyrrol-1-yl)aminocarbonylmethoxy-2-methylindole,
1-furfury l-3-carbethoxy-5-(1, 3, 4-oxadiazol-2-yl)methoxy-2-methylindole and 1-furfuryl-3
carbethoxy-5-(5-mercapto-1, 3, 4-oxadiazol-2-yl)methoxy-2-methylindole. The newly
synthesized compounds are screened for their antibacterial and antifungal activities
Chemoselective reaction of benz[<i>g</i>]indole dicarboxylate towards hydrazine hydrate: Bisheterocycles: Synthesis and antimicrobial activity of some new 1-[2-hydroxyethyl]-3-ethoxycarbonyl-5-oxadiazolyl/triazolyl/ pyrrolylaminocarbonylmethoxy-2-methylbenz[<i>g</i>]indoles
794-800The exclusive formation of
1-[2-hydroxyethyl]-3-ethoxycarbonyl-2-methyl benz[g] indol-5-yloxyacetic
acid hydrazide 6 from
1-[2-hydroxyethyl]-3-ethoxycarbonyl-5-methoxycarbonylmethoxy-2-methylbenz[g]indole 3 revealed
the chemoselectivity of the C5-ester over C3-ester
towards nucleophilic attack of hydrazine hydrate. This monocarbohydrazide 6 is reacted separately with CS2/KOH,
acetonyl acetone and isothiocyanates to secure the desired 1-[2-hydroxyethyl]-3-ethoxycarbonyl-5-(5-mercapto-1,3,4,-oxadiazl-2-y1)methoxy-2-methylbenz[g]indole 7,
1-[2-hydroxyethyl]-3-ethoxy-carbonyl-5-(2,5-dimethylpyrrol-1-yl)aminocarbonylmethoxy-2-methylbenz[g]indole
8 and 1-[2-hydroxyethyl]-3-ethoxycarbonyl-5-(N-substituted
thiosemicarbazinocarbonyl)methoxy-2-methylbenz[g]indole 9a-c. These thiosemicarbazides 9a-c are reacted with 4% NaOH to
produce the 1-[2-hydroxyethyl]2-methybenz[g]indol-5-(4-substituted-5-mercapto-1,2,4-triazol-3-yl)methoxy-3-caboxylic
acids 10a-c. All theses newly
synthsised compounds are screened for their antimicrobial activities
Synthesis and antimicrobial activity of some new 1-cyclohexyl-3-carbethoxy-2-methyl-5- oxadiazolyl/triazolyl and pyrrolylaminocarbonylmethoxyindoles
2896-2900The exclusive formation of 1-cyclohexyl-3-carbethoxy-2-methylindol-5-yloxyacctic
acid hydrazide 3 when 1-cyclohexyl-3-carbethoxy-5-methoxycarbonylmethoxy-2-methylindole
2 is reacted with hydrazine hydrate, reveals the chemoselectivity of C5-ester
over C3-carbethoxy ester function towards the nucleophilic attack of
hydrazine hydrate. This monocarbohydrazide was treated separately with triethylorthoformate,
acetonylacetone in
boiling absolute ethanol, CS2/KOH
and further on acidification with HCl, CS2/KOH followed by treatment
with hydrazine hydrate, KCNS/HCl and treatment with 10% NaOH, to furnish 1-cyclohexyl-3-carbethoxy
-2-methyl-5-(1,3,4-oxadiazol-2-yl) methoxyindole
4, 1-cyclohexyl-3-carbethoxy-2-methyl-5-(2,5-dimethylpyrrol-1-yl)
aminocarbonylmethoxyi ndole 5, 1-cyclohexyl-3-carbethoxy-2-methyl-5-(5-mercapto-1
,3,4-oxadiazol-2-yl) methoxyindole 6 and 1-cyclohexyl-3-carbethoxy-2-methyl
-5-(4-amino-5-mercaptotriazol-3-yl)methoxyindole 7 and 1-cyclohexyl-3-carbethoxy-2-methyl-5-(4H-5-mercapto-1,2,4-triazol-3-yl)methoxyindole
8, respectively. The newly synthesized compounds have been evaluated for
their antimicrobial activity and their structures have been confirmed on the
basis of analytical and spectral data
Chemoselective reaction of indole 1,3-dicarboxylates towards hydrazine hydrate: Bisheterocycles: Synthesis and antimicrobial activity of some new 2-methyl-3-ethoxycarbonyl-1-oxadiazolyl/thiazolidinonyl/pyrrolylaminocarbonylmethylindoles
1663-1668Chemoselectivity
of 1-ester over C3-ester of the indole dicarboxylates 3a,b towards the nucleophilic attack of
hydrazine hydrate has been evidenced by the exclusive formation of
1-hydrazinocarbonylmethyl-3-ethoxycarbonyl-5-substituted-2-methylindoles 5a,b which have been further reacted
separately with CS2/KOH, p-chlorobenzaldehyde and acetonyl
acetone to furnish the 1-(5-mercapto-1,3,4-oxadiazol-2-yl)methyl-3-ethoxycarbonyl-5-substituted-2-methylindoles
6a,b, 1-p-Chlorobenzylidenehydrazinocarbonylmethyl-3-ethoxycarbonyl-5-substituted-2-methylindoles
7a,b and 1-(2,5-dimethylpyrrol-1-yl)aminocarbonylmethyl-3-ethoxycarbonyl-5-substituted-2-methylindoles
8a,b respectively. The Schiff’s bases 7a,b are reacted separately with thioglycolic acid to get the
desired 1-(2-p-chlorophenyl-4-thiazolidinon-1-yl)aminocarbonylmethyl-3-ethoxycarbonyl-5-substituted-2-methylindoles
9a,b. These newly synthesised
compounds are screened for their antibacterial and antifungal activities
<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
1,3-Dipolar cycloaddition reactions: Synthesis and antimicrobial activity of novel 1-triazolylethylindole and 1-triazolylethylbenz[g]indole derivatives
1068-1073Indole azide 4 and benz[g]indole azide 12
are reacted separately with dimethyl acetylenedicarboxylate to secure the
desired
1-[4,5-dimethoxycarbonyl-1,2,3-triazol-1-yl]ethyl-3-ethoxycarbonyl-5-methoxy-2-methylindole
5 and 1-[4,5-dimethoxycarbonyl-1,2,3-triazol-1-yl]ethyl-3-ethoxycarbonyl-5-methoxy-2-methylbenz[g]indole
13, respectively. The reaction of
indole azide 4 and benz[g]indole
azide 12 with ethyl propiolate has
been found to be regiospecific and produce only the
1-[4-ethoxycarbonyl-1,2,3-triazol-1-yl]ethyl-3-ethoxycarbonyl-5-methoxy-2-methylindole
6 and
1-[4-ethoxycarbonyl-1,2,3-triazol-1-yl]ethyl-3-ethoxycarbonyl-5-methoxy-2-methylbenz[g]indole
14, respectively. Indole azide 4 is also reacted with ethyl
phenylpropolate to secure two isomeric products
1-[4-ethoxycarbonyl-5-phenyl-1,2,3-triazol-1-yl]ethyl-3-ethoxycarbonyl-5-methoxy-2-methylindole
8 and
1-[4-phenyl-5-ethoxycarbonyl-1,2,3-triazol-1-yl]ethyl-3-ethoxycarbonyl-5-methoxy-2-methylindole
9. All these newly synthesised
compounds are screened for their antimicrobial activities
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