Advanced Organic Chemistry - I

THEORY 1.

Basic Aspects of Organic Chemistry:

1.

Organic intermediates: Carbocations, carbanions, free radicals, carbenes and nitrenes.

Their method of formation, stability and synthetic applications.

2.

Types of reaction mechanisms and methods of determining them, 3.

Detailed knowledge regarding the reactions, mechanisms and their relative reactivity and orientations.

Addition reactions a) Nucleophilic uni- and bimolecular reactions (SN1 and SN2) b) Elimination reactions (E1 & E2; Hoffman & Saytzeff’s rule) c) Rearrangement reaction Study of mechanism and synthetic applications of following named Reactions:

Ugi reaction, Brook rearrangement, Ullmann coupling reactions, Dieckmann Reaction, Doebner-Miller Reaction, Sandmeyer Reaction, Mitsunobu reaction, Mannich reaction, Vilsmeyer-Haack Reaction, Sharpless asymmetric epoxidation, Baeyer-Villiger oxidation, Shapiro & Suzuki reaction, Ozonolysis and Michael addition reaction Hrs Hrs Synthetic Reagents & Applications:

Aluminiumisopropoxide, N-bromosuccinamide, diazomethane, dicyclohexylcarbodimide, Wilkinson reagent, Witting reagent.

Osmium tetroxide, titanium chloride, diazopropane, diethyl azodicarboxylate, Triphenylphosphine, Benzotriazol-1-yloxy) tris (dimethylamino) phosphonium hexafluoro-phosphate (BOP).

Protecting groups a. Role of protection in organic synthesis b. Protection for the hydroxyl group, including 1,2-and1,3-diols:

ethers, esters, carbonates, cyclic acetals & ketals c. Protection for the Carbonyl Group: Acetals and Ketals d. Protection for the Carboxyl Group: amides and hydrazides, esters e. Protection for the Amino Group and Amino acids: carbamates and amides Heterocyclic Chemistry:

Organic Name reactions with their respective mechanism and application involved in synthesis of drugs containing five, six membered and fused hetrocyclics such as Debus-Radziszewski imidazole synthesis, Knorr Pyrazole Synthesis Pinner Pyrimidine Synthesis, Combes Quinoline Synthesis, Bernthsen Acridine Synthesis, Smiles rearrangement and Traube purine synthesis.

Synthesis of few representative drugs containing these hetrocyclic nucleus such as Ketoconazole, Metronidazole, Miconazole, celecoxib, antipyrin, Metamizole sodium, Terconazole, Alprazolam, Triamterene, Sulfamerazine, Trimethoprim, Hydroxychloroquine, Quinine, Chloroquine, Quinacrine, Amsacrine, Prochlorpherazine, Promazine, Chlorpromazine,Theophylline , Mercaptopurine and Thioguanine.

Hrs Hrs Synthon approach and retrosynthesis applications i.

Basic principles, terminologies and advantages of retrosynthesis; guidelines for dissection of molecules.

Functional group interconvertion and addition (FGI and FGA) ii. C‐X disconnections; C‐C disconnections – alcohols and carbonyl compounds; 1,2‐, 1,3‐,1,4‐, 1,5‐, 1,6‐difunctionalized compounds iii. Strategies for synthesis of three, four, five and six‐membered ring.

Hrs