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UGI Reaction & Brook rearrangement

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UGI Reaction & Brook rearrangement

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Description

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

Transcript

  1. 1. SCHOOL OF PHARMACY, SRTMU NANDED Presented By :- Guided By Madhav D Zade Dr. S.R.Butle
  2. 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. 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. 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. 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. 6. BROOK REARRANGEMENT  -Discovered by Adrien Brook in 1974  -pseudo forest order reaction.  - retention of stereochemistry
  7. 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. 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. 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.

Description

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

Transcript

  1. 1. SCHOOL OF PHARMACY, SRTMU NANDED Presented By :- Guided By Madhav D Zade Dr. S.R.Butle
  2. 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. 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. 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. 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. 6. BROOK REARRANGEMENT  -Discovered by Adrien Brook in 1974  -pseudo forest order reaction.  - retention of stereochemistry
  7. 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. 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. 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.

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