A Convenient One-Pot Synthesis of Substituted 1,1-Dicyanocyclopropanes from Sulfonium Salts, Malononitrile, and Carbonyl Compounds

Synlett

Volumn , Issue 15, 2003, Pages 2309-2312

  Shestopalov, Aleksandr ^a   Rodinovskaya, Lyudmila ^a   Shestopalov, Anatoliy ^a   Zlotin, Sergey ^a   Nesterov, Vladimir ^b  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

Cyclopropanes; Ionic liquid; Multicomponent; Spiroheterocycles; Sulfonium ylides

Indexed keywords

1 BUTYL 3 METHYLIMIDAZOLIUM HEXAFLUOROPHOSPHATE; 1,1 DICYANOCYCLOPROPANE DERIVATIVE; ALCOHOL; ALDEHYDE; CARBONYL DERIVATIVE; CYCLOHEXANE; CYCLOPROPANE DERIVATIVE; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; IONIC LIQUID; KETONE; MALONONITRILE; NITRILE; PIPERIDINE; SPIRO COMPOUND; SULFONIUM DERIVATIVE; TETRAHYDROFURAN; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 0347380049     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42471     Document Type: Article

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25. 3N (0.33 mL, 2.3 mmol). The reaction mixture was stirred at ca 70°C for 10 min and cooled to 20°C, after which stirring was continued for 4-5 h. The precipitate that formed was filtered off and washed successively with 50% and 96% EtOH and hexane. After recrystallization from EtOH, cyclopropanes 7 and 9 were obtained (Table 1).
26. Procedure of Regeneration of the Ionic Liquid: The ionic liquid was successively washed with water, diethyl ether, acetone, and hexane, dried using a rotary evaporator under a reduced pressure, and used in further reactions.
27. 2: C, 74.05; H, 7.46: N, 8.63. Found: C, 73.86; H, 7.29; N, 8.46.
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29. max = 25°). The structure was solved by direct method and refined by full-matrix least squares. Non-hydrogen atoms were refined anisotropically. All hydrogen atoms were placed to the calculated positions. The final R factors were R = 0.0457 (2230 independent reflections) and R = 0.1357 (2796 independent reflections). All calculations were performed using the SHELXL97 program. Details of X-ray analysis including atom coordinates and their isotropic equivalent temperature parameters will be given in a full report.