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ALIGARH MUSLIM
UNIVERSITY
PRESENTED BY-
ANAM ANSARI
INTRODUCTION.
IONIC LIQUIDS: PREPARATION AND PROPERTIES.
SYNTHESIS AND APPLICATION OF:
 FURAN AND DERIVATIVES.
 PYRAN AND DERIVATIVES.
 COUMARINS AND
 DIOXANES.
APPLICATION OF IONIC LIQUIDS IN SYNTHESIS.
CONCLUSION.
REFERENCES.
Oxacycles are part of an extensive group of organic
structures which are used as a synthetic intermedia.
They are also important because of biological,
pharmacological and industrial value of some of the
structures in which they are present.
Most of the reaction media used in traditional chemistry
utilize volatile organic compounds which have several
disadvantages.
Room temperature ionic liquids were introduced as a
novel reaction media in synthesis of oxacyclic
derivatives.
Utilization of RTILs meant some improvement in
relation to reaction yield, reagents selectivity, and
diminution in the reaction time, recyclability, as well as
improvement in environmental condition.
 Ionic liquid is a salt in the liquid state.
 Largely made of ions and short-lived ion pairs.
 They are conductors of electricity, non-ionizing, highly viscous and
frequently exhibit low vapor pressure.
 They show:
 Low combustibility.
 Wide liquid range.
 Excellent thermal stability.
 Favorable solvating properties.
 They are used in:
 Organic Synthesis.
 Chemical Industry.
 Food and Bio products.
 Gas Handling.
 Waste Recycling.
 Pharmaceuticals.
 Dispersant.
 Batteries
IONIC LIQUIDS ARE PREPARED BY
METATHESIS OF HALIDE SALTS.
B:Butyl
m:Methyl
im:Imidazolium
[Bmim][BF4]
1. SYNTHESIS OF FURAN IN Mn(oAc)3 AS CATALYST
AND [Bmim][BF4] AS REACTION MEDIUM
 GENERALLY SYNTHESISED BY 1, 4- DICARBONYL
COMPOUNDS OR
β-KETOESTER UNDER ACID CATALYSIS.
2.SYNTHESIS WITH β-KETOESTERS WITH SAME
REACTION CONDITION
3.SYNTHESIS OF BENZOFURAN IN Ln(OTf)3 AS
CATALYST IN IONIC LIQUID.
80-90%
SYNTHO
N
SOLVEN
T
INSECTI-
CIDE
FURAN
RESIN
PHARMA-
CEUTICAL
S
1.SYNTHESIS OF PYRAN IN [Bmim][PF6]
70-80%
2. MULTICOMPONENT SYNTHESIS IN
[Bmim][BF4]
S NO. SOLVENT TEMPERATURE
(0
C)
TIME (h) YIELD (%)
1 [Bmim][BF4] 80 0.5 98
2 EtOH Reflux 5 76
3 Toluene 80 5 75
4 THF Reflux 5 71
5 [Bmim][BF6] 80 1 90
6 [Bmim][BF4] 80 1 90
TABLE: SOLVENT AND REACTION CONDITIONS
FOR PYRAN DERIVATIVES SYNTHESIS
SYNTHON
ANTIFUNGAL
AGENTS
PHARMAC-
EUTICALS
1.PECHMAN CONDENSATION IN [Bmim]Cl.2ALCl3
2.SYNTHESIS OF BENZOCOUMARIN IN
[Bmim][Al2Cl7]
SYNTHESIS BY THE REACTION OF FORMALDEHYDE
AND STYRENE IN IONIC LIQUID.
DIOXANE
COSM-
ETICS
PHARMAC-
EUTICALS
SOLVENT
Use of RTILs introduces most significant advances in
synthesis of Oxacyclic derivatives.
From the simplest monooxacycles to most
polyoxacycles both are synthesized using RTILs.
The main effects reported by using ionic liquids were
the improvement of reaction yields and the reduction
of reaction time.
Other beneficial effects have been also reported when
used as supported for other media or reaction catalyst
such as silica gel and in microwave assisted synthesis.
RTILs are eco-friendly reaction media and help to
reduce pollution.
 CURRENT ORGANIC SYNTHESIS, 2012, 9, 65-73. MARTA TEIJEIRA AND
MORALES-HELGUERA.
 CHEMICAL COMMUNICATION, 2001, 1350-1351. PARSON AND THOMAS.
 JOURNAL OF ORGANIC CHEMISTRY, 2003, 68,4406-4409.
 TETRAHEDRON LETT. 2004, 45, 5873-5876.
 TETRAHEDRON LETT. 2003, 59, 1599-1604.
 TETRAHEDRON LETT. 2007, 48, 7926-7929.
 APPL.CATAL.A GEN. 2009, 363, 93-99.
 CATAL.COMMUNICATION.2005, 6, 57-60.
 TERAHEDRON LETT. 2005, 46, 3931-3933.
 BIOORG.MED.CHEM.LETT.2010, 20, 809-813.
Presentation anam

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Presentation anam

  • 2. INTRODUCTION. IONIC LIQUIDS: PREPARATION AND PROPERTIES. SYNTHESIS AND APPLICATION OF:  FURAN AND DERIVATIVES.  PYRAN AND DERIVATIVES.  COUMARINS AND  DIOXANES. APPLICATION OF IONIC LIQUIDS IN SYNTHESIS. CONCLUSION. REFERENCES.
  • 3. Oxacycles are part of an extensive group of organic structures which are used as a synthetic intermedia. They are also important because of biological, pharmacological and industrial value of some of the structures in which they are present. Most of the reaction media used in traditional chemistry utilize volatile organic compounds which have several disadvantages. Room temperature ionic liquids were introduced as a novel reaction media in synthesis of oxacyclic derivatives. Utilization of RTILs meant some improvement in relation to reaction yield, reagents selectivity, and diminution in the reaction time, recyclability, as well as improvement in environmental condition.
  • 4.  Ionic liquid is a salt in the liquid state.  Largely made of ions and short-lived ion pairs.  They are conductors of electricity, non-ionizing, highly viscous and frequently exhibit low vapor pressure.  They show:  Low combustibility.  Wide liquid range.  Excellent thermal stability.  Favorable solvating properties.  They are used in:  Organic Synthesis.  Chemical Industry.  Food and Bio products.  Gas Handling.  Waste Recycling.  Pharmaceuticals.  Dispersant.  Batteries
  • 5. IONIC LIQUIDS ARE PREPARED BY METATHESIS OF HALIDE SALTS.
  • 7.
  • 8. 1. SYNTHESIS OF FURAN IN Mn(oAc)3 AS CATALYST AND [Bmim][BF4] AS REACTION MEDIUM  GENERALLY SYNTHESISED BY 1, 4- DICARBONYL COMPOUNDS OR β-KETOESTER UNDER ACID CATALYSIS.
  • 9.
  • 10. 2.SYNTHESIS WITH β-KETOESTERS WITH SAME REACTION CONDITION
  • 11.
  • 12. 3.SYNTHESIS OF BENZOFURAN IN Ln(OTf)3 AS CATALYST IN IONIC LIQUID. 80-90%
  • 14. 1.SYNTHESIS OF PYRAN IN [Bmim][PF6] 70-80%
  • 15. 2. MULTICOMPONENT SYNTHESIS IN [Bmim][BF4]
  • 16. S NO. SOLVENT TEMPERATURE (0 C) TIME (h) YIELD (%) 1 [Bmim][BF4] 80 0.5 98 2 EtOH Reflux 5 76 3 Toluene 80 5 75 4 THF Reflux 5 71 5 [Bmim][BF6] 80 1 90 6 [Bmim][BF4] 80 1 90 TABLE: SOLVENT AND REACTION CONDITIONS FOR PYRAN DERIVATIVES SYNTHESIS
  • 18. 1.PECHMAN CONDENSATION IN [Bmim]Cl.2ALCl3
  • 19.
  • 20. 2.SYNTHESIS OF BENZOCOUMARIN IN [Bmim][Al2Cl7]
  • 21.
  • 22.
  • 23. SYNTHESIS BY THE REACTION OF FORMALDEHYDE AND STYRENE IN IONIC LIQUID.
  • 24.
  • 26.
  • 27. Use of RTILs introduces most significant advances in synthesis of Oxacyclic derivatives. From the simplest monooxacycles to most polyoxacycles both are synthesized using RTILs. The main effects reported by using ionic liquids were the improvement of reaction yields and the reduction of reaction time. Other beneficial effects have been also reported when used as supported for other media or reaction catalyst such as silica gel and in microwave assisted synthesis. RTILs are eco-friendly reaction media and help to reduce pollution.
  • 28.  CURRENT ORGANIC SYNTHESIS, 2012, 9, 65-73. MARTA TEIJEIRA AND MORALES-HELGUERA.  CHEMICAL COMMUNICATION, 2001, 1350-1351. PARSON AND THOMAS.  JOURNAL OF ORGANIC CHEMISTRY, 2003, 68,4406-4409.  TETRAHEDRON LETT. 2004, 45, 5873-5876.  TETRAHEDRON LETT. 2003, 59, 1599-1604.  TETRAHEDRON LETT. 2007, 48, 7926-7929.  APPL.CATAL.A GEN. 2009, 363, 93-99.  CATAL.COMMUNICATION.2005, 6, 57-60.  TERAHEDRON LETT. 2005, 46, 3931-3933.  BIOORG.MED.CHEM.LETT.2010, 20, 809-813.

Editor's Notes

  1. cal