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. ETHYLACETOACETATE
O O
O
ETHYL ACETOACETATE
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3. HETEROCYLCIC APPLICATIONS
• PYROLE(HANTZ SYNTHESIS):
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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.
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5. MECHANISM
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6. Hantzsch pyridine Synthesis
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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"
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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'
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9. FUSED RINGQUINOLINE SYNTHESIS
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10. MECHANISM
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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:
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12. PERKIN REACTION
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13. MECHANISM
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14. HETROCYCLIC APPLICATIONS OF ETHYLCYANO
ACETATE
• PYRIMIDINE:
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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
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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
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17. REFERENCES
• Organic chemistry reactions and reactants :Heterocyclic
compounds
• Organic chemistry portal
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