Bischler- Napieralski Reaction

1. Bischler-Napieralski Reaction Name: Sawsan Jaber Doctor: Fuad mahmmod

2. Table of Contents 1. Objectives 2. Background 3. Reaction and mechanism 4. Application &recent literature 5. Conclusions 6. References

3. objective The object of this research is to know a new information about this reaction And its application.

4. BACKGROUND • IT is an intramolecularelectrophilic aromatic substitutionreaction thatallows for thecyclizationof β-arylethylamides or β-arylethylcarbamates. • It was first discovered in 1893 byAugust BischlerandBernard Napieralski. • in affiliation withBasleChemical Works and theUniversity of Zurich. • The reaction is most notably used in the synthesis of dihydroisoquinolines, which can be subsequentlydehydratedtoisoquinolines.

5. REACTION & MECHNISM

6. the Bischler-Napieralski Reaction involves an initial dehydration step of the amide followed by a cyclization. • Then formed nitrilium salts upon mild heating, whereas the Bischler-Napieralski Reaction required elevated temperatures to form dihydroisoquinolines. • In the dehydration, reagents such as PCl5, POCl3, SOCl2, ZnCl2 can be used to promote loss of the carbonyl oxygen.

7. Application and recent literature • A Versatile Cyclodehydration Reaction for the Synthesis of Isoquinoline and β-Carboline Derivatives

8. this reactions allowed the production of substituted isoquinoline libraries. The generated dihydroisoquinolines and tetrahydroisoquinolines could be oxidized to their corresponding isoquinoline analogues.

9. conclusion • Finely we know that The Bischler–Napieralski reaction is an intramolecular electrophilic aromatic substitution reaction. • And we try to present its reactions.

10. References • http://www.organic-chemistry.org/namedreactions/claisen-condensation.shtm. • August Bischler, Bernard Napieralski (1893). "Zur Kenntniss einer neuen Isochinolinsynthese". Berichte der Deutschen Chemischen Gesellschaft26 (2): 1903.