It includes the UGI reaction & Brook rearrangement. mechanism & application also included that presentation. student will be helpful for easilly available this reaction.

1. SCHOOL OF PHARMACY,
SRTMU NANDED
Presented By :- Guided By
Madhav D Zade Dr. S.R.Butle

2. UGI REACTION
 -discovered by Ivank Ugi in 1968
 -formed peptide bonding formation
 -used four compound &no catalyst used
 -interconversion atomic reaction
 -condensation reaction

3. General Reaction
*
H
O
CH3 NH2
CH3NC CH3COOH CH3 C
O
N
NHCH3CH3
CH3 O
Aldehyde
amine isocynide acid
peptide bonding
H
O
CH3 NH2
CH3NC CH3COOH CH3 C
O
N
NHCH3CH3
CH3 O
Aldehyde
amine isocynide acid
peptide bonding

4. MECHANISM-------
 -firstly aldehyde react with amine & formed intermediate-I
by removal of water molecule.
 -second step react above compound isocynide and formed
intermediate-II
 -these intermediate react with acid and formed peptide
bonding and also called UGI Reaction.

5. O
acetaldehyde
H2N
methyl amine
N
H2
O
H
NHO
acetaldehyde
H
H
CH3
HN
CH3 C
H
NH
CH3
CH3
H
C NH
CH3
CH3 N C
CH3 CH N
C N CH3
CH3
H
O
HO
acetic acid
CH3 C
H
H
N CH3
O C
N
(Z)
CH3
CH3
H
O
H3C C
H
C N
N C
CH3
CH3
H
CH3
OH
O
H3C
H
N C
H
C N C CH3
O OCH3CH3
peptide bonding formation

6. BROOK REARRANGEMENT
 -Discovered by Adrien Brook in 1974
 -pseudo forest order reaction.
 - retention of stereochemistry

7. MECHANISM----
 Rearrangement of α-silyl oxy-anion to car anion via
reversible process involving pentad-coordinate
silicon intermediate or [1,2]-silly migration.

8. General Reaction
Mechanism :-
CH3 C SiH3
OH
CH3
CH3 Li
CH3 Li
O
CH3
SiH3
CH3 SiH3
O
CH3
H
Base
CH3 SiH3
O
CH3
CH3 SiH
CH3
O
H
CH3 C
O
CH3
SiH3
H2O
CH3 H
O
CH3
SiH3
Silyl ether
Silane

9. Application:
 -analogue of phosphate brook rearrangement of 1-hydroxy
phosphonates has also been reported.
 -alkylation of brook rearrangement.
 -synthesis of scalaren dye using acyl silane.
 -stereospecific & regiospecific synthesis of enol silly ether.
 -potential application.