JAWAHARLAL NEHRU TECHNOLOGICAL UNIVERSITY HYDERABAD

Course Objective

The content of Unit I and II are mainly aimed at utilization of different synthetic

reagents used in the preparation of intermediates and final compounds and also aimed at the principles of green chemistry. Unit III and IV contents are mainly aimed at scale of processes for the preparation of new pharmaceutical agents and also to design different synthetic strategies. Unit V is mainly aimed to utilize the knowledge of chemical library for drug design

Course Outcome

The student would be in a position to have advanced knowledge of different

synthetic reagents and reaction processes, synthetic routes by involving green chemistry principles. The student would also have techniques to utilize the chemical library of combinatorial chemistry.

UNIT - I

Synthetic Reagents & Applications: Lead Tetra Acetate (LTA), N- Bromosuccinimide (NBS), Osmium Tetroxide, Lithium Aluminum Hydride (LAH) and Sodium Borohydride, Dicyclohexylcarbodimide (DCC) and 2,3-dichlro-5,6-dicyano-1,4-benzoquinone (DDQ). A brief account on Green Chemistry: Principles and applications

UNIT - II

Catalysis:

• a. Types of catalysis, heterogeneous and homogenous catalysis, advantages and disadvantages
• b. Heterogeneous catalysis – preparation, characterization, kinetics, supported catalysts, catalyst deactivation and regeneration, some examples of heterogeneous catalysis used in synthesis of drugs.
• c. Homogenous catalysis, hydrogenation, hydroformylation, hydrocyanation, Wilkinson catalysts, chiral ligands and chiral induction, Ziegler‐Natta catalysts, some examples of homogenous catalysis used in synthesis of drugs
• d. Transition-metal and Organo-catalysis in organic synthesis: Metal-catalyzed reactions
• e. Biocatalysis: Use of enzymes in organic synthesis, immobilized enzymes/cells in organic reaction.
• f. Phase transfer catalysis ‐theory and applications

UNIT - III

Molecular Rearrangements & their applications:

• 1. Carbon to Carbon Migration: Wagner – Meerwin rearrangement, Claisen rearrangement and benzil – benzilic acid rearrangement.
• 2. Carbon to Nitrogen Migration: Hoffmann rearrangement, Curtius rearrangement and Lossen rearrangement, Beckman rearrangement.
• 3. Carbon to Oxygen Migration: Bayor – Villiger rearrangement, Rearrangement of hydro peroxides and Wittig rearrangement.

UNIT - IV

Chemistry of peptides

• a. Coupling reactions in peptide synthesis
• b. Principles of solid phase peptide synthesis, t-BOC and FMOC protocols, various solid supports and linkers: Activation procedures, peptide bond formation, deprotection and cleavage from resin, low and high HF cleavage protocols, formation of free peptides and peptide amides, purification and case studies, site-specific chemical modifications of peptides
• c. Segment and sequential strategies for solution phase peptide synthesis with any two case studies
• d. Side reactions in peptide synthesis: Deletion peptides, side reactions initiated by proton abstraction, protonation, overactivation and side reactions of individual amino acids.

UNIT - V

Combinatorial Chemistry: Introduction, solid phase techniques, parallel synthesis, mixed combinatorial chemistry, diconvulution techniques, tagging, photolithography, limitations of combinatorial chemistry, planning and designing of combinatorial synthesis.

RECOMMENDED BOOKS:

• 1. W. Carruthers, Some Modern Methods of Org. Synthesis, III rd Edition, Cambridge University Press, Cambridge (1988)
• 2. Gorgy Keri and Istarian Toth, Molecular Patho-mechanisms and New Trends in Drug Research – Taylor and Francis Group, London 2003
• 3. Organic Chemistry, V Algarsamy, Pharmamed Press.
• 4. R.K. Mackie, A Guidebook to Organic Thesis – Prentice Hall
• 5. T.W. Greene and PGM Warts, Protecting Groups – John Willey
• 6. Michael B. Smith, Organic Synthesis
• 7. Organic synthesis- Special techniques VK Ahluwalia and R Aggarwal, Narosa Publishers.
• 8. “Organic Chemistry” Vol I and II. I.L. Finar. ELBS, Sixth ed., 1995.
• 9. “Advanced Organic chemistry, Reaction, mechanisms and structure”, JMarch, John Wiley and sons, New York.
• 10. Principles of organic synthesis, ROC Norman and JMCoxan, Nelson thorns
• 11. Carey, Organic chemistry, 5th edition (Viva Books Pvt. Ltd.) M.Pharm I Year II Sem (Pharmaceutical Chemistry)