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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 3 a-Reaction carried out with ethyl chloroacetate in presence of K2CO3 and acetone; b- reaction carried out with hydrazine hydrate in ethanol.
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Figure 0001: Synthetic route for the synthesis of 3 a-Reaction carried out with ethyl chloroacetate in presence of K2CO3 and acetone; b- reaction carried out with hydrazine hydrate in ethanol.

Mentions: The required starting material to accomplish the synthesis of title compounds, ethyl naphtho[2,1-b]furan-2-carboxylate (2) was obtained by the reaction of 2-hydroxy-1-naphthaldehyde (1) with ethyl chloroacetate in presence of anhydrous potassium carbonate and in dry DMF at reflux temperature. Both condensation as well as cyclisation occurred in single step and produced ethyl naphtho-[2,1-b]furan-2-carboxylate (2) in good yield. The reaction of ethyl naphtho-[2,1-b]furan-2-carboxylate (2) with hydrazine hydrate in presence of acid catalyst in ethanol produced naphtho-[2,1-b]furan-2-carbohydrazide (3). The synthetic route is shown in Scheme 1.


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 3 a-Reaction carried out with ethyl chloroacetate in presence of K2CO3 and acetone; b- reaction carried out with hydrazine hydrate in ethanol.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

Figure 0001: Synthetic route for the synthesis of 3 a-Reaction carried out with ethyl chloroacetate in presence of K2CO3 and acetone; b- reaction carried out with hydrazine hydrate in ethanol.
Mentions: The required starting material to accomplish the synthesis of title compounds, ethyl naphtho[2,1-b]furan-2-carboxylate (2) was obtained by the reaction of 2-hydroxy-1-naphthaldehyde (1) with ethyl chloroacetate in presence of anhydrous potassium carbonate and in dry DMF at reflux temperature. Both condensation as well as cyclisation occurred in single step and produced ethyl naphtho-[2,1-b]furan-2-carboxylate (2) in good yield. The reaction of ethyl naphtho-[2,1-b]furan-2-carboxylate (2) with hydrazine hydrate in presence of acid catalyst in ethanol produced naphtho-[2,1-b]furan-2-carbohydrazide (3). The synthetic route is shown in Scheme 1.

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