ChemInform Abstract: HETEROCYCLISCHE ANALOGA VON XANTHONEN 3. MITT. THIOCHROMONO(3,2‐D)PYRAZOLE

Sarenko, A. S.; Poznyakova, L. N.; Kvitko, I. Ya.; Efros, L. S.

doi:10.1002/chin.197240292

Cited by 3 publications

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“…In the same manner, thiones 7 and 9 , required for comparison purposes, were synthesized from oxo compounds 6 and 8 , respectively (Scheme ). The latter were prepared according to known procedures ( 6 ,2, 20 8 21).…”

Section: Resultsmentioning

confidence: 99%

“…To a solution of the appropriate oxo compound ( 4a–j ,1–3 6 ,2 8 21) (1 mmol) in toluene (15 ml) was added Lawesson's reagent (202 mg, 0.5 mmol) and the mixture was heated to reflux overnight (∼14 h). Then, the solvent was removed under reduced pressure and the residue was subjected to column chromatography (silica gel, eluent: CH 2 Cl 2 or CH 2 Cl 2 MeOH, 100:3) to afford the colored thiones 5a–j, 7, and 9 .…”

Section: Methodsmentioning

confidence: 99%

“…Yield: 98%; mp: 185–187 °C (literature20 mp: 189–190 °C); MS: m / z (%) = 293 (M + + 1, 21), 292 (M + , 100), 291 (M + − 1, 33), 146 (11), 91 (18), 77 (23), 51 (15). C 17 H 12 N 2 OS (292.35).…”

Section: Methodsmentioning

confidence: 99%

“…Yield: 86%; mp: 183–185 °C (literature21 mp: 208–210 °C); MS: m / z (%) = 309 (M + + 1, 23), 308 (M + , 100), 307 (M + − 1, 48), 263 (26), 172 (19), 146 (11), 138 (12), 120 (11), 83 (10), 77 (51), 69 (27), 57 (22), 55 (17), 51 (44). C 17 H 12 N 2 S 2 (308.42).…”

Section: Methodsunclassified

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Heterocyclic analogs of xanthiones: 5,6‐fused 3‐methyl‐1‐phenylpyrano[2,3‐c]pyrazol‐4(1H) thiones—synthesis and NMR (¹H, ¹³C, ¹⁵N) data

Huemer

Eller

Hölzer

2010

Magnetic Reson in Chemistry

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Various [5,6]pyrano[2,3-c]pyrazol-4(1H)-thiones were synthesized in high yields by treatment of the corresponding [5,6]pyrano[2,3-c]pyrazol-4(1H)-ones with Lawesson's reagent. Detailed NMR spectroscopic studies were undertaken of the title compounds. Complete and unambiguous assignment of chemical shifts ((1)H, (13)C, (15)N) and coupling constants ((1)H,(1)H; (13)C,(1)H) was achieved by the combined application of various one- and two-dimensional (1D and 2D) NMR spectroscopic techniques. Unequivocal mapping of most (13)C,(1)H spin coupling constants is accomplished by 2D (delta, J) long-range INEPT spectra with selective excitation.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsunclassified

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Heterocyclic analogs of xanthiones: 5,6‐fused 3‐methyl‐1‐phenylpyrano[2,3‐c]pyrazol‐4(1H) thiones—synthesis and NMR (¹H, ¹³C, ¹⁵N) data

Huemer

Eller

Hölzer

2010

Magnetic Reson in Chemistry

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“…A mixture of (1,3-dimethyl-5-hydroxy-1H-pyrazol-4-yl)-phenylmethanone (1a) [34] (2.162 g, 10 mmoles) and phosphorus oxychloride (3.067 g, 20 mmoles) was heated to reflux for 2 hours. Then the mixture was poured onto ice-water (50 ml) and neutralized with 40% aqueous sodium hydroxide.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of substituted 3‐phenyl‐6h‐pyrazolo[4,3‐d]isoxazoles from corresponding 4‐benzoyl‐5‐hydroxypyrazoles

Hölzer

Hahn

2003

Journal of Heterocyclic Chem

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Treatment of 1,(3)‐(di)substituted 4‐benzoyl‐5‐hydroxypyrazoles with phosphorus oxychloride affords the corresponding 4‐benzoyl‐5‐chloropyrazoles. Reaction of the latter with hydroxylamine leads to oximes, which can be cyclized to novel 3‐phenyl‐6H‐pyrazolo[4,3‐d]isoxazoles by treatment with sodium hydride in dimethyl formamide. Detailed nmr spectroscopic studies (1H, 13C) with all obtained compounds are presented.

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Spiro-Fused (C2)-Azirino-(C4)-pyrazolones, a New Heterocyclic System. Synthesis, Spectroscopic Studies and X-ray Structure Analysis¹

et al. 2003

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Reaction of 1-substituted 4-acyl-5-hydroxy-3-methyl-1H-pyrazoles (2) with hydroxylamine gives the corresponding "oximes" 3, which are mainly present as (Z)-2,4-dihydro-4-[(hydroxyamino)methylene]-3H-pyrazol-3-ones. Treatment of compounds 3 with trichloroacetyl isocyanate/potassium carbonate in anhydrous diethyl ether affords 7-methyl-1,5,6-triazaspiro[2.4]hepta-1,6-dien-4-ones (4). The structure of compounds 4 was elucidated by means of single-crystal X-ray analysis (4f, 4h) and confirmed by NMR spectroscopic investigations ((1)H, (13)C).

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ChemInform Abstract: HETEROCYCLISCHE ANALOGA VON XANTHONEN 3. MITT. THIOCHROMONO(3,2‐D)PYRAZOLE

Abstract: 1,3‐Disubstituierte 4‐(o‐Chlorbenzoyl)‐5‐pyrazolone (I) werden bei 100°C (7 Stdn.) mit Phosphoroxychlorid behandelt.

Cited by 3 publications

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Heterocyclic analogs of xanthiones: 5,6‐fused 3‐methyl‐1‐phenylpyrano[2,3‐c]pyrazol‐4(1H) thiones—synthesis and NMR (¹H, ¹³C, ¹⁵N) data

Heterocyclic analogs of xanthiones: 5,6‐fused 3‐methyl‐1‐phenylpyrano[2,3‐c]pyrazol‐4(1H) thiones—synthesis and NMR (¹H, ¹³C, ¹⁵N) data

Synthesis of substituted 3‐phenyl‐6h‐pyrazolo[4,3‐d]isoxazoles from corresponding 4‐benzoyl‐5‐hydroxypyrazoles

Spiro-Fused (C2)-Azirino-(C4)-pyrazolones, a New Heterocyclic System. Synthesis, Spectroscopic Studies and X-ray Structure Analysis¹

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ChemInform Abstract: HETEROCYCLISCHE ANALOGA VON XANTHONEN 3. MITT. THIOCHROMONO(3,2‐D)PYRAZOLE

Abstract: 1,3‐Disubstituierte 4‐(o‐Chlorbenzoyl)‐5‐pyrazolone (I) werden bei 100°C (7 Stdn.) mit Phosphoroxychlorid behandelt.

Cited by 3 publications

References 0 publications

Heterocyclic analogs of xanthiones: 5,6‐fused 3‐methyl‐1‐phenylpyrano[2,3‐c]pyrazol‐4(1H) thiones—synthesis and NMR (1H, 13C, 15N) data

Heterocyclic analogs of xanthiones: 5,6‐fused 3‐methyl‐1‐phenylpyrano[2,3‐c]pyrazol‐4(1H) thiones—synthesis and NMR (1H, 13C, 15N) data

Synthesis of substituted 3‐phenyl‐6h‐pyrazolo[4,3‐d]isoxazoles from corresponding 4‐benzoyl‐5‐hydroxypyrazoles

Spiro-Fused (C2)-Azirino-(C4)-pyrazolones, a New Heterocyclic System. Synthesis, Spectroscopic Studies and X-ray Structure Analysis1

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Heterocyclic analogs of xanthiones: 5,6‐fused 3‐methyl‐1‐phenylpyrano[2,3‐c]pyrazol‐4(1H) thiones—synthesis and NMR (¹H, ¹³C, ¹⁵N) data

Heterocyclic analogs of xanthiones: 5,6‐fused 3‐methyl‐1‐phenylpyrano[2,3‐c]pyrazol‐4(1H) thiones—synthesis and NMR (¹H, ¹³C, ¹⁵N) data

Spiro-Fused (C2)-Azirino-(C4)-pyrazolones, a New Heterocyclic System. Synthesis, Spectroscopic Studies and X-ray Structure Analysis¹