Nitrogen Containing Heterocycles

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Presentation transcript:

Nitrogen Containing Heterocycles 3-Membered Ring 12/1/2018

Nitrogen Containing Heterocycles 3-Membered Ring in our system? How do these work? 12/1/2018

Higher Heterocycles Containing Nitrogen Basic Ring Systems Acid – Base Properties Ist pKA ? IInd pKA ? Stability to Water, Acid and Base Without substituents ? With substituents ? 12/1/2018

Higher Heterocycles Containing Nitrogen Examples of Drugs … 4-membered ring Importance of b-lactam ring in activity …… generation of resistance!! 12/1/2018

Higher Heterocycles Containing Nitrogen Examples of Drugs … 5-membered ring (anti-hyperlipidemic agent) (anti-histaminic) 12/1/2018

Higher Heterocycles Containing Nitrogen and Another Heteroatom Five membered Rings Acid – Base Properties Ist pKA ? IInd pKA ? Why is imidazole not basic ? pKA with greater substitution ? Stability to Water, Acid and Base Without substituents ? With substituents ? 12/1/2018

Higher Heterocycles Containing Nitrogen and Another Heteroatom Examples of such heterocycles in Drugs (anti-biotic agent) (anti-biotic agent) (pain medication) 12/1/2018

Heterocycles Containing Sulfur Basic Ring Systems Examples in Drugs (Antihistamine) (Antibiotic) (Antimalarial) 12/1/2018

Complex Heterocycles Examples in Drugs (Antibiotic) (Antihypertensive) (for pneumonia) (Antihypertensive) (Anti-infectious) (Anti-seizure) 12/1/2018

6 Membered Nitrogen Containing Heterocycles Examples in Drugs 12/1/2018

Barbiturates / Barbituric Acids (Keto form) pKA = ~4 Phenytoin (anti-psychotic) (Enol form) 12/1/2018

Heterocycles More Complex Unsaturated Ring Systems 6-membered and higher heterocycles 12/1/2018

Azepine diazepine oxazepine Heterocycles More Complex Unsaturated Ring Systems 6-membered and higher heterocycles Azepine diazepine oxazepine 12/1/2018

7 and 8 Membered Nitrogen Containing Heterocycles 12/1/2018

Heterocycles Electrophilic Aromatic Substitution in Heterocycles heterocycles generally react well with electrophiles; better than benzene (except for pyridines) their stability to metabolic enzymes is generally lower than their carbocyclic analogs EAS occurs at the 2-position of 5-membered heterocycles EAS occurs at the 3-position of 6-membered heterocycles 12/1/2018