Practical Synthesis of 7-Azaserotonin and 7-Azamelatonin

A practical method for synthesizing 7-azaserotonin and 7-azamelatonin was developed by using 3-bromo-5-methoxy-1-tosyl-2,3dihydro-1H-pyrrolo[2,3-b]pyridin-2-ol as a starting material. This compound is a useful reactant for the formal C3-electrophilic reaction. The lactone derivative obtained by the reaction with Meldrum's acid was used as a key intermediate, in which the C-2 unit was introduced into the 7-azaindole skeleton.

Automated summary

A practical method for synthesizing 7-azaserotonin and 7-azamelatonin was developed using a useful starting material, introducing new functional groups into the compounds.