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Synlett
Volumn , Issue 8, 2007, Pages 1289-1293
A novel approach for the conversion of primary amides into tetrazoles by using tributyltin chloride and sodium azide in the presence of DMF
Author keywords

DMF; Irbesartan; O xylene; Primary acid amides; Sodium azide; Tributyltin chloride
Indexed keywords

2 ALKYL [4 (2 AMINODOPHENYL)BENZYL] 1,3 DIAZASPIRO[4.4]NON 1 EN 4 ONE DERIVATIVE; 4 [ALPHA )ACYLAMINO)CYLOPENTAMIDOMETHYL] 2' CARBOXAMIDOBIPHENYL DERIVATIVE; AMIDE; BIPHENYL DERIVATIVE; IRBESARTAN; SODIUM AZIDE; SPIRONOLACTONE; TETRAZOLE DERIVATIVE; TRIBUTYLTIN CHLORIDE; UNCLASSIFIED DRUG;
EID: 34249786258     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/S-2007-977458     Document Type: Article
Times cited : (7)
References (14)
  • 2
    • 84943405513 scopus 로고
    • Katritzky, A. R, Rees, C. W, Eds, Pergamon Press: Oxford
    • Butler, R. N. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: Oxford, 1984, 791-838.
    • (1984) Comprehensive Heterocyclic Chemistry , pp. 791-838
    • Butler, R.N.1
  • 11
    • 34249786736 scopus 로고    scopus 로고
    • Solvents and reagents were obtained from commercial sources and used without purification. Melting points were determined on a Polmon melting point apparatus. All melting points are uncorrected. The 1H NMR and 13C NMR spectra were recorded on a Bruker 300 spectrometer at 300 MHz and 75 MHz, respectively. The chemical shifts are reported in δ (ppm) relative to TMS. The mass spectra were recorded on a API 2000 Perkin Elmer PE-SCIEX mass spectrometer. Synthesis of 2-(4-Aminomethylphenyl)benzamide Hydrochloride (2, 2-(4-Aminomethylphenyl)benzonitrile hydrochloride (150 g, 0.614 mol) was neutralized in a mixture of CH2Cl2 (750 mL) and H2O (300 mL) at 15-20 °C by the addition of NaOH (25.90 g, 0.647 mol, The organic layer was separated and washed with H2O and concentrated. The concentrated mass was dissolved in t-BuOH (450 mL) and heated to 65 °C. Freshly prepared KOH powder 48.52 g, 85, 0.736 m
    • -].
  • 12
    • 34249786108 scopus 로고    scopus 로고
    • Typical Experimental Procedure for the Synthesis of 4-[α-(n-Acylamino)cyclopentamidomethyl, 2′-carboxamidobiphenyls 3a-e: Compound 2 (115 g, 0.438 mol) was added to a mixture of dicyclohexylcarbodiimide (DCC; 99.36 g, 0.482 mol) in CH2Cl2 (2300 mL) followed by compound 1a 10 (93.38 g, 0.438 mol) at 25-30 °C. Thereafter, N-hydroxybenzotriazole (11.85g, 0.087 mol) was added followed by diisopropylethylamine (62.70 g, 0.482 mol) and heated to reflux for 6 h. The reaction mixture was cooled to 25 °C and the salts were filtered. The filtrate was washed with H2O (230 mL) followed by sat. Na 2CO3 solution (575 mL) and concentrated to a 1200-mL The slurry obtained was cooled to 10-15 °C and stirred for 1 h. The solid was filtered and washed with precooled CH2Cl2 (230 mL) and dried to afford compound 3b as a white powder; mp
    • 3: C, 69.02; H. 6.34; N, 11.50. Found: C, 69.11; H. 6.34; N, 11.51.
  • 13
    • 34249809574 scopus 로고    scopus 로고
    • Typical Experimental Procedure for the Synthesis of 2-Alkyl-3-[p-(o-amidophenyl)benzyl]-1, 3-diazaspiro|4.4|non-l-en-4-ones4a-e: Trifluoroacetic acid (15.5 g, 0.136 mol) was added to a preheated suspension of 4-[α-(n-pentanoylamino) cyclopentamidomethyl]-2′-carbox-amidobiphenyl (3b; 50 g, 0.124 mol) in o-xylene (500 mL) over a period of 30 min. Thereafter, the mixture was heated to reflux for 18 h. Xylene was distilled off and a mixture of EtOAc (750 mL) and H2O (250 mL) was added at 55 °C and the reaction mixture was cooled to r.t. The pH was adjusted to 9.0-9.5 with aq NH3 and stirred for 5 min. The organic layer was separated and washed with H 2O 250 mL, The organic layer was concentrated to a of about 250 mL and cooled to 0-5 °C. The slurry obtained was stirred for 30 min to complete the crystallization. The solid obtained was filtered and washed with precooled
    • 3: C, 72.60; H, 6.09; N, 12.10. Found: C, 72.70; H, 6.10; N, 12.11.
  • 14
    • 34249785817 scopus 로고    scopus 로고
    • Typical Experimental Procedure for the Synthesis of 2-Alkyl-3-[2′-(1H-tetrazol-5-yl)(1,1′-biphenyl-4-yl) methyl]-1,3-diazaspiro[4.4]non-1-en-4-ones 5a, e: Sodium azide (16.20 g, 0.249 mol) was added to tributyltin chloride (81 g, 0.249 mol) at 25-30 °C under a nitrogen atmosphere and the contents were stirred for 30 min at the same temperature. Thereafter, DMF (13 g, 0.18 mol) was added at 25-30 °C and the Stirring continued for 30 min at temperatures below 45 °C. o-Xylene (50 mL) was added followed by 2-(n-butyl)-3-[p-(o- amidophenyl)benzyl]-1,3-diazaspiro[4.4]non-1-en-4-one (4b; 50 g, 0.124 mol, The temperature was raised to 150-155 °C and the stirring was continued for 60 h at the same temperature under nitrogen atmosphere. Thereafter, the reaction mixture was cooled to 25 °C and diluted with CH2,Cl2 (200 mL, o-xylene (100 mL) and H 2O (100 mL) at the
    • 6): δ = 0.70-0.91 (t, J = 7.41 Hz, 3 H), 1.20-140 (sext, 2 H), 145-1.60 (quint, 2 H), 1.60-2.00 (m, 8 H), 2.20-240 (t. J = 6.04 Hz, 2 H), ...

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