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hetreocyclic applications of ethyl aceto acetate & ethyl cyano acetate

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hetreocyclic applications of ethyl aceto acetate & ethyl cyano acetate

  1. 1. A SEMINAR ON HETROCYLIC APPLICATIONS OF ETHYL ACETOACETATE, ETHYL CYANO ACETATE GUIDED BY: PRESENTED BY: MR.SAYAN DUTTA GUPTHA G.SHRAVANI R.NO:170213884010
  2. 2. ETHYLACETOACETATE O O O ETHYL ACETOACETATE 10/25/2014 2
  3. 3. HETEROCYLCIC APPLICATIONS • PYROLE(HANTZ SYNTHESIS): 10/25/2014 3
  4. 4. MECHANISM • The mechanism starts with amine (1) attacking the β- carbon of β- keto esters (2) & forms an enamine(3).The enamine attacks the carbonyl carbon of α-ketones(4).This is followed by the loss of H2O,giving the imine(5).This intermediate undergoes an intramolecular nucleophilic attack forming 5-membered ring (6).Hydrogen is eliminated and the π-bonds are rearranged in the ring ,yielding the final product. • The other mechanism includes the enamines (3) attacks the α- carbon of the α-halo ketone(4) as a part of a nucleophilic substitution instead of carbonyl carbon. 10/25/2014 4
  5. 5. MECHANISM 10/25/2014 5
  6. 6. Hantzsch pyridine Synthesis 10/25/2014 6
  7. 7. Intermediate -1 O R H + O O -H2O R' OR" R' O O OR" R Intermediate-2 O O R' OR" + NH3 -H2O R' NH2 O OR" 10/25/2014 7
  8. 8. Reaction between two intermediates R' NH2 O OR" R' O R OR" + -H2O O "ROOC CO N H R' OR " R' H R Oxidation "ROOC COOR" NH R' R' H R R R"OOC COOR" R' N R' 10/25/2014 8
  9. 9. FUSED RINGQUINOLINE SYNTHESIS 10/25/2014 9
  10. 10. MECHANISM 10/25/2014 10
  11. 11. A 2007 study revised the reaction mechanism and based on NMR spectroscopy and theoretical calculations favors an O,O-dicationic intermediate (a super electrophile) over the N,O dicationic intermediate . For preparative purposes triflic acid is recommended: 10/25/2014 11
  12. 12. PERKIN REACTION 10/25/2014 12
  13. 13. MECHANISM 10/25/2014 13
  14. 14. HETROCYCLIC APPLICATIONS OF ETHYLCYANO ACETATE • PYRIMIDINE: 10/25/2014 14
  15. 15. THEOBROMINE NH2 O H2N UREA COOC2H5 CH2-CN NaNH2 HN O N CH3 NH2 NH4SH HNO2 HN N CH3 NH2 NH2 O Fused with acetic acid HN NH HN N O CH3I NaOC2H5 N CH3 N N HN O CH3 THEOBROMINE 10/25/2014 15
  16. 16. THEOPHYLINE COOC2H5 CH2-CN N O N CH3 NH2 H3C HO O FORMIC ACID N O O N CH3 H3C HN N CH3 CH3 H-N-CO-N-H 10/25/2014 16
  17. 17. REFERENCES • Organic chemistry reactions and reactants :Heterocyclic compounds • Organic chemistry portal 10/25/2014 17
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