6533b826fe1ef96bd1285186
RESEARCH PRODUCT
Acceptorless dehydrogenative condensation: synthesis of indoles and quinolines from diols and anilines.
Rafael BallesterosRafael Ballesteros-garridoRamón J. ZaragozáM. José AurellDelia Bellezzasubject
010405 organic chemistryChemistryOrganic ChemistryCondensationDiol010402 general chemistryCondensation reaction01 natural sciencesBiochemistry0104 chemical sciencesCatalysisSolventchemistry.chemical_compoundReagentOrganic chemistryOrganic synthesisPhysical and Theoretical Chemistrydescription
The use of diols and anilines as reagents for the preparation of indoles represents a challenge in organic synthesis. By means of acceptorless dehydrogenative condensation, heterocycles, such as indoles, can be obtained. Herein we present an experimental and theoretical study for this purpose employing heterogeneous catalysts Pt/Al2O3 and ZnO in combination with an acid catalyst (p-TSA) and NMP as solvent. Under our optimized conditions, the diol excess has been reduced down to 2 equivalents. This represents a major advance, and allows the use of other diols. 2,3-Butanediol or 1,2-cyclohexanediol has been employed affording 2,3-dimethyl indoles and tetrahydrocarbazoles. In addition, 1,3-propanediol has been employed to prepare quinolines or natural and synthetic julolidines.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2021-01-06 | Organicbiomolecular chemistry |