HETEROCYCLIC CHEMISTRY

1. Identify and draw the structures of various fused heterocyclic systems.
2. Explain the chemical reactions and mechanistic aspects of fused heterocyclic structures.
3. Describe the synthesis of fused heterocyclic systems and design synthetic routes for similar compounds.
4. Explain the applications of heterocyclic systems in drug synthesis.
5. Identify heterocyclic structures in biologically active compounds.
6. Predict the chemical behavior of novel heterocyclic compounds based on their structure.

13 weeks, about 39 hours in total. Yours will differ.

1. Week 1Module 1: Benzopyridines

   • Unit 1: Reactions of Quinolines · 3 hours

     Read the introduction to understand the structure and properties of quinolines.. Study electrophilic substitution reactions at positions 5 and 8.. Practice writing reactions of quinolines with acids and Lewis acids..

2. Week 2Module 1: Benzopyridines

   • Unit 2: Synthesis of Quinolines · 3 hours

     Understand the Skraup synthesis of quinoline and its applications.. Learn the Dӧbner-von Miller synthesis and its use of α, β-unsaturated carbonyl compounds.. Study the Conrad-Limpach synthesis and Friedlaender synthesis..

3. Week 3Module 1: Benzopyridines

   • Unit 3: Application of the Quinoline Ring System in Drug Synthesis · 3 hours

     Identify biologically active compounds containing the quinoline nucleus.. Describe synthetic routes to quinoline derivatives of medicinal importance.. Study the applications of quinolines in drug synthesis, including quinine and chloroquine..

4. Week 4Module 1: Benzopyridines

   • Unit 4: Synthesis and Reactions of Iso-quinolines · 3 hours

     Differentiate between isoquinoline and quinoline.. Study reactions with electrophiles and nucleophiles.. Understand the Bischler-Napieralski synthesis of isoquinolines..

5. Week 5Module 1: Benzopyridines

   • Unit 5: Application of the Iso-quinoline Ring System in Drug Synthesis · 3 hours

     Identify medicinal agents containing the isoquinoline ring system.. Learn about the importance of isoquinoline derivatives in medicine.. Study the synthesis of papaverine and morphine..

6. Week 6Module 2: Benzofuran, Benzothiophene and Indoles

   • Unit 1: Reactions of Benzopyrrole (Indole) · 3 hours

     Identify and draw the indole structure.. Study electrophilic substitution reactions, focusing on C-3 substitution.. Understand the Vilsmeier formylation and Mannich reaction..

7. Week 7Module 2: Benzofuran, Benzothiophene and Indoles

   • Unit 2: Synthesis of Benzopyrrole (Indole) · 3 hours

     Understand the Fischer-Indole synthesis and its limitations.. Study the Reissert synthesis and Wender synthesis.. Learn about the Leimgruber-Batcho indole synthesis..

8. Week 8Module 2: Benzofuran, Benzothiophene and Indoles

   • Unit 3: Application of Indole in Drug Synthesis · 3 hours

     State the importance of the indole nucleus in medicine.. Trace the synthetic route of indomethacin.. Study the applications of indole in drug synthesis, including vinca alkaloids..

9. Week 9Module 2: Benzofuran, Benzothiophene and Indoles

   • Unit 4: Synthesis and Reactions of Benzofuran and Benzothiophene · 3 hours

     Draw the structure of benzofuran and benzothiophene.. Study electrophilic substitution reactions of benzofurans and benzothiophenes.. Understand the synthesis of benzofurans and benzothiophenes..

10. Week 10Module 2: Benzofuran, Benzothiophene and Indoles

    • Unit 5: Applications of the Benzofuran and Benzothiophene Ring System in Drug Synthesis · 3 hours

      Explain how pharmacologically active compounds are derived from benzofuran and benzothiophene.. Study the applications of benzofuran and benzothiophene derivatives in medicine.. Learn about amiodarone, sertaconazole, and raloxifene..

11. Week 11Module 3: Dibenzopyrones, Pyrilium Salts and Other Benzopyrones

    • Unit 1: Synthesis and Reactions of Coumarins · 3 hours

      Identify the coumarin structure.. Study nucleophilic and electrophilic reactions of coumarins.. Understand the synthesis of coumarins from 2-hydroxybenzaldehyde and malonic acid..

12. Week 12Module 3: Dibenzopyrones, Pyrilium Salts and Other Benzopyrones

    • Unit 2: Reactions of Chromones · 3 hours

      Identify the chromone structure.. Study electrophilic substitution and nucleophilic addition reactions of chromones.. Understand the formation of salts with strong acids..

13. Week 13Module 3: Dibenzopyrones, Pyrilium Salts and Other Benzopyrones

    • Unit 3: Synthesis of Chromones · 3 hours

      Explain the synthesis of chromones from 2-hydroxyphenyl ketones.. Study the synthesis of 2- and 3-substituted chromones.. Understand the Claisen-like condensation in chromone synthesis..