A New Method for Synthesis of 1<i>H</i>-Pyrazol-3(2<i>H</i>)-ones

Magedov, I. V.; Smushkevich, Yu. I.

doi:10.1055/s-1991-26588

Cited by 11 publications

(7 citation statements)

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“…3‐{[2‐(Phenylacetyl)hydrazino]carbonyloxy}benzoic Acid 5a (typical procedure): 33 At 0 °C, a solution of phenylacetylhydrazine (150 mg, 1 mmol) and dimethylaniline (133 mg, 1.1 mmol) in THF (3 mL) was added with stirring to a solution of chlorocarbonate 13 obtained from 94 mg (0.5 mmol) of tert ‐butyl 3‐hydroxybenzoate. The mixture was stirred for 3 h at room temperature.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Hydrolysis, and Evaluation of 3-Acylamino-3,4-dihydro-2-oxo-2H-1,3-benzoxazinecarboxylic Acids and Linear Azadepsipeptides as Potential Substrates/Inhibitors of β-Lactam-Recognizing Enzymes

et al. 2001

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The title compounds can be considered as stabilized aza analogs of previously studied dihydrobenzopyranones and linear depsipeptides, which behave as substrates or inhibitors of β-lactamases. Treatment of substituted hydrazides 9b and 9bЈ with a phosgene substitute resulted in a series of N-methylated 3-acylamino-3,4-dihydro-2-oxo-2H-1,3-benzoxazine-7-and -8-carboxylic acids 2b and 2bЈ. However, in the case of the corresponding free NH hydrazide 9a(m), a competitive cyclization gave instead a stable 4H-1,3,4-oxadiazol-5-one 10a. To avoid this unwanted cyclization, an N-(p-methoxy)-benzylated hydrazide 9bЈЈ was prepared. After formation of the benzoxazinone ring with carbonyldiimidazole, the removal of this new N 1 -hydrazide protecting group was achieved with methanesulfonic acid in trifluoroacetic acid to give the expected 3-phenacetamido-3,4-dihydro-2-oxo-2H-

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Section: Methodsmentioning

confidence: 99%

Synthesis, Hydrolysis, and Evaluation of 3-Acylamino-3,4-dihydro-2-oxo-2H-1,3-benzoxazinecarboxylic Acids and Linear Azadepsipeptides as Potential Substrates/Inhibitors of β-Lactam-Recognizing Enzymes

et al. 2001

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“…The mixture was stirred at 0°C for 10 min and then at room temperature for 3 h. The solution containing the crude 3tert-butoxycarbonylphenyl chlorocarbonate 13 was used directly in the next step of the reaction sequence. [33] At 0°C, a solution of phenylacetylhydrazine (150 mg, 1 mmol) and dimethylaniline (133 mg, 1.1 mmol) in THF (3 mL) was added with stirring to a solution of chlorocarbonate 13 obtained from 94 mg (0.5 mmol) of tert-butyl 3-hydroxybenzoate. The mixture was stirred for 3 h at room temperature.…”

Section: -Tert-butoxycarbonylphenyl Chlorocarbonate 13mentioning

confidence: 99%

Synthesis, Hydrolysis, and Evaluation of 3-Acylamino-3,4-dihydro-2-oxo-2H-1,3-benzoxazinecarboxylic Acids and Linear Azadepsipeptides as Potential Substrates/Inhibitors of β-Lactam-Recognizing Enzymes

et al. 2001

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The title compounds can be considered as stabilized aza analogs of previously studied dihydrobenzopyranones and linear depsipeptides, which behave as substrates or inhibitors of βlactamases. Treatment of substituted hydrazides 9b and 9bЈ with a phosgene substitute resulted in a series of N-methylated 3-acylamino-3,4-dihydro-2-oxo-2H-1,3-benzoxazine-7and -8-carboxylic acids 2b and 2bЈ. However, in the case of the corresponding free NH hydrazide 9a(m), a competitive cyclization gave instead a stable 4H-1,3,4-oxadiazol-5-one 10a. To avoid this unwanted cyclization, an N-(p-methoxy)benzylated hydrazide 9bЈЈ was prepared. After formation of the benzoxazinone ring with carbonyldiimidazole, the removal of this new N 1 -hydrazide protecting group was achieved with methanesulfonic acid in trifluoroacetic acid to give the expected 3-phenacetamido-3,4-dihydro-2-oxo-2H- [a] SIRCOB,

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“…For general background to and the pharmaceutical applications of hydrazine derivatives, see: Bredihhin & Mä eorg (2008); Ragnarsson (2001); Ling et al (2001). For further synthesis details, see: Magedov & Smushkevich (1991). For standard bond-length data, see: Allen et al (1987).…”

Section: Related Literaturementioning

confidence: 99%

“…The title compound was prepared by the reaction of 2-phenylacetyl chloride with 2-phenylacetohydrazide in the presence of sodium carbonate in water at 5-10 °C (Magedov & Smushkevich, 1991).…”

Section: S2 Experimentalmentioning

confidence: 99%

2-Phenyl-N′-(2-phenylacetyl)acetohydrazide

2012

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Key indicators: single-crystal X-ray study; T = 100 K; mean (C-C) = 0.002 Å; R factor = 0.041; wR factor = 0.134; data-to-parameter ratio = 14.1.In the title compound, C 16 H 16 N 2 O 2 , the N 0 -acetylacetohydrazide group is approximately planar (r.m.s. deviation = 0.018 Å for the eight non-H atoms) and makes dihedral angles of 81.92 (6) and 65.19 (6) with the terminal phenyl rings. The phenyl rings form a dihedral angle of 62.60 (7) . In the crystal, molecules are linked into sheets lying parallel to (001)

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A New Method for Synthesis of 1H-Pyrazol-3(2H)-ones

Cited by 11 publications

References 0 publications

Synthesis, Hydrolysis, and Evaluation of 3-Acylamino-3,4-dihydro-2-oxo-2H-1,3-benzoxazinecarboxylic Acids and Linear Azadepsipeptides as Potential Substrates/Inhibitors of β-Lactam-Recognizing Enzymes

Synthesis, Hydrolysis, and Evaluation of 3-Acylamino-3,4-dihydro-2-oxo-2H-1,3-benzoxazinecarboxylic Acids and Linear Azadepsipeptides as Potential Substrates/Inhibitors of β-Lactam-Recognizing Enzymes

Synthesis, Hydrolysis, and Evaluation of 3-Acylamino-3,4-dihydro-2-oxo-2H-1,3-benzoxazinecarboxylic Acids and Linear Azadepsipeptides as Potential Substrates/Inhibitors of β-Lactam-Recognizing Enzymes

2-Phenyl-N′-(2-phenylacetyl)acetohydrazide

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