N′-[(E)-(3-Phenyl-1H-pyrazol-4-yl)methyl­idene]naphtho­[2,1-b]furan-2-carbohydrazide monohydrate

نویسندگان

  • Hoong-Kun Fun
  • Wan-Sin Loh
  • Shridhar Malladi
  • B. M. Ganesh
  • Arun M. Isloor
چکیده

In the title hydrate, C(23)H(16)N(4)O(2)·H(2)O, the pyrazole ring is approximately planar, with a maximum deviation of 0.023 (1) Å, and makes dihedral angles of 28.63 (6) and 46.44 (7)° with the naphtho-[2,1-b]furan ring system and the benzene ring, respectively, In the crystal, O-H⋯N, O-H⋯O, N-H⋯O, N-H⋯N, C-H⋯O and C-H⋯N hydrogen bonds link the mol-ecules, forming sheets lying parallel to the ab plane. The crystal structure also features C-H⋯π inter-actions involving the centroids of the pyrazole and benzene rings.

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منابع مشابه

Synthesis, reactions and biological evaluation of some new naphtho[2,1-b]furan derivatives bearing a pyrazole nucleus.

Vilsmeier formylation of 2-(1-phenylhydrazonoethyl)naphtho[2,1-b]furan (2) gave 3-naphtho[2,1-b]furan-2-yl-1-phenyl-1H-pyrazole-4-carbaldehyde (3), which was reacted with C- and N-nucleophiles to afford naphthofuranpyrazol derivatives 4-8. Treatment of 2-[(3-(naphtho[2,1-b]furan-2-yl)-1-phenyl-1H-pyrazol-4-yl)methylene]-malononitrile (4a) with reactants having active hydrogen and Et₃N gave the ...

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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

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 pr...

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(Z)-4-[(Ethyl­amino)(furan-2-yl)methyl­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

In the crystal of the title compound, C(17)H(17)N(3)O(2), the mol-ecules exist in the keto-enamine form. The pyrazole ring is oriented at 10.59 (4) and 57.98 (5)° to the phenyl and furyl rings, respectively, and the dihedral angle between phenyl and furyl rings is 73.30 (11)°. An intra-molecular N-H⋯O hydrogen bond occurs between imino and carbonyl groups. In the crystal, weak C-H⋯O hydrogen bo...

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4-{[(E)-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)methyl­idene]amino}-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

The title Schiff base compound, C(23)H(23)N(5)O, was synthesized by the reaction of 4-amino-phenazone and 3,5-dimethyl-1-phenyl-pyrazole-4-carbaxaldehyde. The mol-ecule adopts an E configuration about the central C=N double bond. A weak intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. The dihedral angle between the pyrazole rings is 24.72 (10)° and the dihedral angles between t...

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4-{[(1,3-Benzothia­zolium-2-yl)hydra­zono](phen­yl)meth­yl}-3-methyl-1-phenyl-1H-pyrazol-5-olate monohydrate

The title compound, C(24)H(19)N(5)OS·H(2)O, was synthesized by the reaction of 4-benzoyl-3-methyl-1-phenyl-pyrazol-5-one and 2-hydrazino-1,3-benzothia-zole. Proton transfer leads to the formation of a zwitterionic structure and the mol-ecule exists in the enolate form. The pyrazolone ring makes dihedral angles of 35.4 (3), 69.7 (3) and 40.1 (3)° with the 1-phenyl, indirectly bound phenyl and be...

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عنوان ژورنال:

دوره 67  شماره 

صفحات  -

تاریخ انتشار 2011