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Synlett
Volumn , Issue 19, 2007, Pages 2979-2982
Pyrolytic methods in organic synthesis: Novel routes for the synthesis of 3-oxoalkanenitriles, 2-acyl anilines, and 2-aroyl anilines
Author keywords

Aminoacetophenone derivative; HMBC 15N NMR; Microwave heating
Indexed keywords

2 ACYL ANILINE DERIVATIVE; 2 AROYL ANILINE DERIVATIVE; 3 OXOALKANENITRILE DERIVATIVE; AMINOPYRIDINE; ANILINE DERIVATIVE; CHLORIDE; HYDROXYLAMMONIUM; NITRILE; PYRIDINE; UNCLASSIFIED DRUG;
EID: 37249075344     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-992355     Document Type: Article
Times cited : (52)
References (31)
  • 12
    • 37249092207 scopus 로고    scopus 로고
    • Microwave heating was carried out with a single-mode cavity explorer microwave synthesizer, CEM Corporation, NC, USA
    • Microwave heating was carried out with a single-mode cavity explorer microwave synthesizer, CEM Corporation, NC, USA.
  • 13
    • 0011932271 scopus 로고    scopus 로고
    • Loupy, A, Ed, Wiley-VCH: Weinheim
    • Microwaves in Organic Synthesis; Loupy, A., Ed.; Wiley-VCH: Weinheim, 2002.
    • (2002) Microwaves in Organic Synthesis
  • 16
    • 37249070033 scopus 로고    scopus 로고
    • 15N and NOE spectra were measured using Bruker Avance II 600 MHz superconducting spectrometer, and FT-IR measurements were performed with a Perkin Elmer 2000 FT-IR system. Mass spectrometric analysis was carried out on a VG-Autospec-Q high performance tri-sector GC/MS/MS.
    • 15N and NOE spectra were measured using Bruker Avance II 600 MHz superconducting spectrometer, and FT-IR measurements were performed with a Perkin Elmer 2000 FT-IR system. Mass spectrometric analysis was carried out on a VG-Autospec-Q high performance tri-sector GC/MS/MS.
  • 17
    • 37249089126 scopus 로고    scopus 로고
    • General Method for Preparation of Compounds 3a,b Method A: Arylacetonitrile (10 mmol) was refluxed in pyridine (20 mL) for 8 h. The solvent was evaporated under vacuum, and the solid product was collected by filtration and crystallized from DMF-EtOH. Method B: Arylacetonitrile 1a in pyridine (2 mL) was heated alone for 1.5 min in a microwave oven, the reaction mixture was then poured on cold H2O. The so-formed solid product was collected by filtration and crystallized from EtOH-DMF. 5′-Amino- 6′-benzoyl-[1,1′;3′,1″]terphenyl-2′, 4′-dicarbonitrile (3a) Yield 78, mp 295°C. MS: m/z, 399(40, IR: 3437 and 3175 (NH2, 2224 and 2199 (2 CN, 1654 (CO) cm-1. 1H NMR (400 MHz, DMSO, δ, 7.52-7.83 (m, 15 H, PhH, 8.01 (br s, 2 H, NH2, 13C NMR 100 MHz, DMSO, δ, 80.0, 100.7, 116.5, 118.2, 119.5, 128.5, 128.6, 128.9, 129, 129.2, 129
    • 13C NMR (100 MHz, DMSO): δ = 80.0, 100.7, 116.5, 118.2, 119.5, 128.5, 128.6, 128.9, 129, 129.2, 129.6, 130.7, 131.8, 132.0, 133.4, 135.9, 137.6, 155.3, 155.8, 157.0, 186.7.
  • 22
    • 37249068241 scopus 로고    scopus 로고
    • General Method for Preparation of Compounds 7 A mixture of each of the enaminones 6 (10 mmol, NH2OH·HCl (20 mmol, and NaOAc (20 mmol) was stirred in EtOH-H2O mixture for 2 h at r.t. The reaction mixture was then poured on cold H2O. The so-formed solid product was collected by filtration and crystallized from EtOH. 3-Oxo-3-thiophen-2-yl-propionaldehyde Oxime (7c) Yield 78, mp 118-120°C MS: m/z 169. IR: 3197 (OH, 1653 (CO) cm-1. 1H NMR (400 MHz, DMSO, δ, 3.92 (d, 2 H, CH2, 4.02 (d, 2 H, CH2, 7.00 (t, 1 H, vinyl-H, 7.26 (dd, 1 H, thiophene H4, 7.50 (t, 1 H, vinyl-H, 8.03 (d, 1 H, thiophene-H3, 8.05 (d, 1 H, thiophene-H5, 13C NMR 100 MHz, DMSO, δ, 36.03, 36.2, 50.5, 52.3, 125.9, 127.02, 127.7, 129.7, 134.8, 135.1, 136.1, 136.2, 143.9, 144.02, 145.3, 148.7, 189.6, 190.5
    • 13C NMR (100 MHz, DMSO): δ = 36.03, 36.2, 50.5, 52.3, 125.9, 127.02, 127.7, 129.7, 134.8, 135.1, 136.1, 136.2, 143.9, 144.02, 145.3, 148.7, 189.6, 190.5.
  • 23
    • 37249031133 scopus 로고    scopus 로고
    • General Procedures for Preparation of 1a-d A mixture of each of the oximes 7 (10 mmol), diethyloxalate (10 mmol), and NaH (20 mmol) in dioxane (5 mL) was stirred for 2 h at r.t. The reaction mixture was then evaporated and triturated with EtOH. The so-formed solid product was collected by filtration and crystallized from EtOH.
    • General Procedures for Preparation of 1a-d A mixture of each of the oximes 7 (10 mmol), diethyloxalate (10 mmol), and NaH (20 mmol) in dioxane (5 mL) was stirred for 2 h at r.t. The reaction mixture was then evaporated and triturated with EtOH. The so-formed solid product was collected by filtration and crystallized from EtOH.
  • 29
    • 37249045192 scopus 로고    scopus 로고
    • General Method for Preparation of Compounds 14, 17, 18, and 20 3-Aminocrotononitrile (10 mmol) was refluxed in pyridine (20 mL) for 8 h. The solvent was evaporated under vacuum, and the solid product was collected by filtration. The mixture of the three compounds was separated by means of column chromatography on silica gel with EtOAc-PE (1:4) as eluent. 4-Amino-2,6- dimethylnicotinonitrile (14) Yield 30, mp 313°C MS: m/z, 148. IR: 3367, 3358 (NH2, 2211 (CN) cm-1. 1H NMR (400 MHz, DMSO, δ, 2.42 (s, 3 H, CH3, 2.60 (s, 3 H, CH 3, 7.65 (s, 1 H, vinyl-H, 10.62 (s, 2 H, NH2, 13C NMR (100 MHz, DMSO, δ, 20.8, 23.6, 101.5, 110.5, 117.5, 152.4, 155.0, 161.2. 6-Amino-2,4-dimethylnicotinonitrile (17) Yield 32, mp 230°C MS: m/z, 148. IR: 3391, 3336 (NH2, 2212 (CN) cm-1. 1H NMR (400 MHz, DMSO, δ, 2.23 s, 3 H, CH
    • 13C NMR (100 MHz, DMSO): δ = 20.8, 21.65, 24.2, 75.6. 102.1, 111.3, 117.7, 121, 152.0, 154.6, 156.3, 161.7.
  • 31
    • 37249050563 scopus 로고    scopus 로고
    • 13C NMR (100 MHz, DMSO): δ = 18.2, 20.1, 90.9, 116.2, 149.5, 150.5, 154.8, 161.6.
    • 13C NMR (100 MHz, DMSO): δ = 18.2, 20.1, 90.9, 116.2, 149.5, 150.5, 154.8, 161.6.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.