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Volumn , Issue 5, 2009, Pages 0755-0758

Convenient one-pot synthesis of N-substituted 3-trifluoroacetyl pyrroles

Author keywords

3 trifluoroacetylpyrroles; Antimicrobial activity; Dihydrofuran; N substituted pyrroles; Pyrroles

Indexed keywords

1,1,1 TRIFLUORO 3 (2 ETHANAL) 4 ALKYLAMINOBUT 3 EN 2 ONE; 1,1,1 TRIFLUORO 3 (2 HYDROXYETHYL) 4 ALKYLAMINOBUT 3 EN 2 ONE; 3 TRIFLUOROACETYL 4,5 DIHYDROFURAN; 3 TRIFLUOROACETYL PYRROLE; AMINE; ISONIAZID; PYRROLE DERIVATIVE; RIFAMPICIN; UNCLASSIFIED DRUG;

EID: 62349131504     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087821     Document Type: Article
Times cited : (17)

References (56)
  • 23
  • 31
    • 26444594265 scopus 로고    scopus 로고
    • For recent examples, see: a
    • For recent examples, see: (a) Salamone, S. G.; Dudley, G. B. Org. Lett. 2005, 7, 4443.
    • (2005) Org. Lett , vol.7 , pp. 4443
    • Salamone, S.G.1    Dudley, G.B.2
  • 40
    • 62349112492 scopus 로고    scopus 로고
    • Rv and RMPr (MIC = 6.25 μg/mL) and INHr (MIC = 12.5 μg/mL).
    • Rv and RMPr (MIC = 6.25 μg/mL) and INHr (MIC = 12.5 μg/mL).
  • 53
    • 62349128896 scopus 로고    scopus 로고
    • Synthesis of N-Substituted 3-Trifluoroacetyl Pyrroles 5, General Procedure To a solution of 3-trifluoroacetyl-4,5-dihydrofuran 1 (0.50 g, 3.0 mmol) in CH2Cl2 (5 mL, amines 2a,b (approx. 6.0 mmol, amines 2c-r (3.0 mmol, and amines 2s-u (1.5 mmol) were added under magnetic stirring, and the reaction was stirred for 30 min at r.t. After this period, PCC (4.5 mmol) in CH2Cl2 (5 mL) was added, and the reaction mixture was refluxed for 3 h. For amines 2a,b, before the addition of PCC, the reaction was extracted with CH 2Cl2 (3 x 15 mL) and dried with MgSO4. The solvent was evaporated by rotary evaporator, and the reaction residue was treated with 1 M solution of NaOH and extracted with Et2O (3 x 50 mL, The combined organic layers were washed with 1 M NaOH solution (2 x 50 mL) and distilled H2O 1 x 50 mL, The organic phase was dried with anhyd MgS
    • 2O (50 mL).
  • 54
    • 62349109235 scopus 로고    scopus 로고
    • Spectroscopic Data of Selected Compounds 1-Methyl-3- trifluoroacetylpyrrole (5b) 1H NMR (200 MHz, CDCl3, δ, 7.4 (s, 1 H, 6.7 (s, 1 H, 6.6 (s, 1 H, 3.7 (s, 1 H, 13C NMR (100 MHz, CDCl3, δ, 175.0 (q, 2J CF, 35.3 Hz, 130.1, 124.3, 117.8, 116.9 (q, 1JCF, 288.7 Hz, 110.9, 36.8. GC-MS (IE, 70eV, m/z, 117 (68, M, 108 (100, 80 (30, ESI-HRMS: m/z calcd for C6H4F3NO [M, H, 178.0479; found: 178.0471. 1-(Ethan-1-ol-2-yl)-3-trifluoroacetylpyrrole (5g) 1H NMR (400 MHz, CDCl3, δ, 7.5 (s, 1 H, 6.7 (m, 2 H, 4 (t, 1 H, J, 9.2 Hz, 3.9 (t, 1 H, J, 9.2 Hz, 13C NMR (100 MHz, CDCl3, δ, 175.4 (q, 2JCF, 35.7 Hz, 130.1, 123.8, 117.8, 116.9 q, 1JCF, 288
    • +: 367.0881; found: 367.0876.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.