by arzoo dharasandia@gmail.com

1. NAMED ORGANIC
REACTIONS
PREPARED BY: DHARASANDIA ARZOO P
GUIDED BY : UTTAM MORE
DEPARTMENT OF PHARMACEUTICAL CHEMISTRY
SHREE DHANVANTRY PHARMACY COLLEGE

2. UGI REACTION
four component condensation (4cc) of : carboxylic acid
C-isocynides
amines
and carbonyl compounds
TO AFFORD DIAMIDES

3. UGI REACTION
 Developed in 1959 by Ivar Ugi
 The most studied and used MCR
 Involves an isocyanide, a carboxylic
acid, an amine and a carbonyl
compound to yield
α-aminoacyl amides
α-acylamino
carboxamides

4. UGI REACTION
+ +

6. Applications of ugi reaction
 Phenol Ugi-Smiles Systems: Strategies for the Multicomponent N-Arylation of
Primary Amines with Isocyanides, Aldehydes, and Phenols
 2-Bromo-6-isocyanopyridine as a Universal Convertible Isocyanide for
Multicomponent Chemistry.

7. Pharmaceutical application
 Crixivan can be prepared
using the Ugi reaction.
 Additionally, many of
the caine-type
anesthetics are
synthesized using this
reaction. Examples
include lidocaine and bu
pivacaine.
indinavir
lidocaine
bupivacaine

8. Ullmann reaction
 There are two different transformations referred as the Ullmann Reaction. The "classic"
Ullmann Reaction is the synthesis of symmetric biaryls via copper-catalyzed coupling. for
example; The synthesis of biaryls by the copper-induces coupling of aryl halides is called
Ullmann reaction. Iodobenzene is heated with copper powder,biphenyl is formed in 80% .
 The "Ullmann-type" Reactions include copper-catalyzed Nucleophilic Aromatic Substitution
between various nucleophiles (e.g. substituted phenoxides) with aryl halides. The most
common of these is the Ullmann Ether Synthesis.

9. Classic Ullmann coupling reaction

10. Ullmann reaction machanism
 Biaryls are available through coupling of the aryl halide with an excess of copper at elevated
temperatures (200 °C). The active species is a copper(I)-compound which undergoes oxidative addition
with the second equivalent of halide, followed by reductive elimination and the formation of the aryl-
aryl carbon bond.
 Another possibility is the use of Cu(I) for the oxidative coupling of aryllithium compounds at low
temperatures. This method can also be used to generate asymmetric biaryls, after addition of the
appropriate halide.

11. Mechanism conti….

12. Applications of Ullmann coupling reaction
 An Improved Cu-Based Catalyst System for the Reactions of Alcohols with Aryl Halides.
 An Efficient Ullmann-Type C-O Bond Formation Catalyzed by an Air-Stable Copper(I)-
Bipyridyl Complex.

13. Brook rearrangement
 The Brook rearrangement in organic chemistry is a rearrangement reaction in which
an organosilyl group switches position with a hydroxyl proton over a carbon to
oxygen covalent bond under the influence of a base.
 It is named for the Canadian chemist Adrian Gibbs Brook (1924–2013). The reaction product
is a silyl ether.

14. mechanism

15. application
 Preparation of 1-Siloxy-1-alkenylcopper Species by 1,2-Csp2-to-O Silyl Migration of
Acylsilane

16. mechanism