SCOPUS 정보 검색 플랫폼

Volumn , Issue 12, 2009, Pages 1955-1958

Studies on fluorinated annulated nicotines: Concise synthesis of cis-4,4-difluoro-2,3,3a,4,5,9b-hexahydro-1-methyl-1H-pyrrolo[2,3-f]quinoline

(2) Cheng, Bin a,b Zhai, Hongbin a,b

a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA (China)

b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY (China)

Author keywords

Fluorinated; Intramolecular azomethine ylide alkene 3+2 cycloaddition; Nicotine analogue; Rigid conformation

Indexed keywords

3 BROMO 3,3 DIFLUOROPROPENE; 4,4 DIFLUORO 2,3,3A 4,5,9B HEXAHYDRO 1 METHYL 1H PYRROLO [2,3 F] QUINOLINE; 6,6,5 TRICYCLIC DIFLUORINATED NICOTINE DERIVATIVE; AZOMETHINE YLIDE; CARBENE; DIFLUOROMETHYLENE; INDIUM; NICOTINE DERIVATIVE; PROPYLENE; QUINOLINE; UNCLASSIFIED DRUG;

ALLYLATION; ANNULATION REACTION; ARTICLE; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORINATION; SYNTHESIS;

EID: 67651204137 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0029-1217519 Document Type: Article

Times cited : (6)

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- Preparation of New Compounds Compound 5 Indium powder (67 mg, 0.58 mmol) and 3-bromo-3,3-difluoropropene (70 μL, 0.72 mmol) were added sequentially to a solution of 4 (94 mg, 0.45 mmol) in DMF (3 mL, The mixture was then sonicated for 3 h. After evaporation of DMF under reduced pressure, sat. aq NaHCO3 soln and EtOAc were added. The two layers were separated, and the aqueous layer was further extracted with EtOAc. The combined organic layers were dried (Na2SO4, filtered, and concentrated to give a residue, which was chromatographed (EtOAc-PE, 1:5) to afford 5 (100 mg, 78, as a colorless oil: 1H NMR (300 MHz, CDCl3, δ, 1.16 (t, J, 9.2 Hz, 3 H, 1.27 (t, J, 9.9 Hz, 3 H, 3.36-3.50 (m, 2 H, 3.54-3.65 (m, 1 H, 3.74-3.82 (m, 1 H, 4.99 (d, J, 9.6 Hz, 1 H, 5.36-5.45 (m, 1 H, 5.49 (d, J, 11.1 Hz, 1 H, 5.61-5.69 (m, 1 H, 5.88 (s, 1 H, 5.92-6.02 (m, 1 H, 7.31 dd
- 3 soln and the mixture was extracted with EtOAc.

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