Organic Chemistry-Synthesis of Benzothiophene

organic Chemistry Synthesis

1. SYNTHESIS OF BENZOTHIOPHENE
DERIVATIVESBYPD-CATALYZEDOR
RADICAL-PROMOTED
HETEROCYCLODEHYDRATION OF1-(2-
MERCAPTOPHENYL)-2-YN-1-OLS
Presentation by:
Jacobo Guevara Mendoza
Chemical Research

3. OBJECTIVE
•Novel approach
of direct
synthesis of
benzothiophene
derivatives.
oHeterocyclization
of1-(2-
mercaptophenyl)-
2-yn-1-ols 2or 4.
oFrom alkynylation
of 2-
mercaptobenzaldehy
des or 1-(2-
mercaptophenyl)
ketones 1.
oDepending on the
reaction conditions,
either Pd-catalyzedor
radical-promoted may
take place,gives good
to high yields

4. INTRODUCTION
•Benzothiophenesare a very important class of
heterocyclic compounds.
•The benzothiophenecore is present in many natural and
pharmacological active compounds.
•Benzothiophenesfind extensive application in materials
science.
•Synthesis of this structure has recently attractedmuch
attention and manyefficient methods have beendeveloped.

5. Pharmaceutical use:
•Raloxifene:prevent and treat
bone loss
•Zileuton:inhibits
lipoxygenase
•Benocyclidine:psychoactive
recreational drug
•Mobam:antipsychotic
•Sertaconazole:antifungal

6. METHODS
Heterocyclodehydration

7. RESULTS

8. RESULTS

9. RESULTS

10. CONCLUSION
•In conclusion, the availability 1-(2-mercaptophenyl)-2-yn-1-ols 2and 4, easily obtained as
crudeproducts from alkynylation of 2-mercaptobenzaldehydes or 1-(2-mercaptophenyl)
ketones 1, are excellent substrates for the direct synthesis of benzothiophenederivatives 3and
5.