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Synthesis and Activity Evaluation of 2-(1-naphtho[2,1-b]furan-2-yl-carbonyl)-3,5-disubstituted-2,3-dihydro-1H-pyrazoles.

Kumaraswamy MN, Chandrashekhar C, Shivakumar H, Prathima Mathias DA, Mahadevan KM, Vaidya VP - Indian J Pharm Sci (2008)

Bottom Line: The reaction of naphtho[2,1-b]furan-2-carbohydrazide (3) with chalcones (6a-6o) in presence of acetic acid as catalyst in dioxane produces 1-(naphtho[2,1-b]furan-2-yl-carbonyl)-3,5-disubstituted-2,3-dihydro-1H-pyrazoles (7a-o).The structures of newly synthesized compounds have been established by elemental analysis and spectral studies.The compounds 7a-o have been evaluated for their antimicrobial activity and some selected compounds evaluated for antiinflammatory, analgesic, anthelmintic, diuretic and antipyretic activities.

View Article: PubMed Central - PubMed

Affiliation: Department of PG Studies and Research in Chemistry, School of Chemical Sciences, Kuvempu University, Jnana Sahyadri, Shankaraghatta-577 451, India.

ABSTRACT
Ethyl naphtho[2,1-b]furan-2-carboxylate (2) on reaction with hydrazine hydrate in presence of acid catalyst in ethanol medium affords naphtho[2,1-b]furan-2-carbohydrazide (3). The reaction of substituted acetophenones (4a-c) with aromatic aldehydes (5a-e) produces chalcones (6a-o) via the Claisen condensation. The reaction of naphtho[2,1-b]furan-2-carbohydrazide (3) with chalcones (6a-6o) in presence of acetic acid as catalyst in dioxane produces 1-(naphtho[2,1-b]furan-2-yl-carbonyl)-3,5-disubstituted-2,3-dihydro-1H-pyrazoles (7a-o). The structures of newly synthesized compounds have been established by elemental analysis and spectral studies. The compounds 7a-o have been evaluated for their antimicrobial activity and some selected compounds evaluated for antiinflammatory, analgesic, anthelmintic, diuretic and antipyretic activities.

No MeSH data available.


Related in: MedlinePlus

Synthetic route for the synthesis of 7a-o a- Reaction carried out in acetic acid and dioxane at reflux temperature.
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Figure 0003: Synthetic route for the synthesis of 7a-o a- Reaction carried out in acetic acid and dioxane at reflux temperature.

Mentions: The reaction of naphtho[2,1-b]furan-2-carbohydrazide (3) with chalcones 6a-o to obtain the title compounds (7a-o) was attempted by employing various reagents and reaction conditions. However, the desired condensation was successful only when the reaction was carried out by using acetic acid as catalyst and dioxane as a solvent at reflux temperature. The target compounds 1-(naphtho[2,1-b]furan-2-ylcarbonyl)-3,5-disubstituted-2,3dihydro-1H-pyrazoles (7a-o) were obtained in good yield. The synthetic route is shown in Scheme 3.


Synthesis and Activity Evaluation of 2-(1-naphtho[2,1-b]furan-2-yl-carbonyl)-3,5-disubstituted-2,3-dihydro-1H-pyrazoles.

Kumaraswamy MN, Chandrashekhar C, Shivakumar H, Prathima Mathias DA, Mahadevan KM, Vaidya VP - Indian J Pharm Sci (2008)

Synthetic route for the synthesis of 7a-o a- Reaction carried out in acetic acid and dioxane at reflux temperature.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3040863&req=5

Figure 0003: Synthetic route for the synthesis of 7a-o a- Reaction carried out in acetic acid and dioxane at reflux temperature.
Mentions: The reaction of naphtho[2,1-b]furan-2-carbohydrazide (3) with chalcones 6a-o to obtain the title compounds (7a-o) was attempted by employing various reagents and reaction conditions. However, the desired condensation was successful only when the reaction was carried out by using acetic acid as catalyst and dioxane as a solvent at reflux temperature. The target compounds 1-(naphtho[2,1-b]furan-2-ylcarbonyl)-3,5-disubstituted-2,3dihydro-1H-pyrazoles (7a-o) were obtained in good yield. The synthetic route is shown in Scheme 3.

Bottom Line: The reaction of naphtho[2,1-b]furan-2-carbohydrazide (3) with chalcones (6a-6o) in presence of acetic acid as catalyst in dioxane produces 1-(naphtho[2,1-b]furan-2-yl-carbonyl)-3,5-disubstituted-2,3-dihydro-1H-pyrazoles (7a-o).The structures of newly synthesized compounds have been established by elemental analysis and spectral studies.The compounds 7a-o have been evaluated for their antimicrobial activity and some selected compounds evaluated for antiinflammatory, analgesic, anthelmintic, diuretic and antipyretic activities.

View Article: PubMed Central - PubMed

Affiliation: Department of PG Studies and Research in Chemistry, School of Chemical Sciences, Kuvempu University, Jnana Sahyadri, Shankaraghatta-577 451, India.

ABSTRACT
Ethyl naphtho[2,1-b]furan-2-carboxylate (2) on reaction with hydrazine hydrate in presence of acid catalyst in ethanol medium affords naphtho[2,1-b]furan-2-carbohydrazide (3). The reaction of substituted acetophenones (4a-c) with aromatic aldehydes (5a-e) produces chalcones (6a-o) via the Claisen condensation. The reaction of naphtho[2,1-b]furan-2-carbohydrazide (3) with chalcones (6a-6o) in presence of acetic acid as catalyst in dioxane produces 1-(naphtho[2,1-b]furan-2-yl-carbonyl)-3,5-disubstituted-2,3-dihydro-1H-pyrazoles (7a-o). The structures of newly synthesized compounds have been established by elemental analysis and spectral studies. The compounds 7a-o have been evaluated for their antimicrobial activity and some selected compounds evaluated for antiinflammatory, analgesic, anthelmintic, diuretic and antipyretic activities.

No MeSH data available.


Related in: MedlinePlus