Synthesis of Some Spirochroman-4-Ones by Regioselective [4+2] Cycloaddition Reactions

Title: Synthesis of Some Spirochroman-4-Ones by Regioselective [4+2] Cycloaddition Reactions

Volume: 4 Issue: 3

Author(s): Moheddine Askri, Mohamed Rammah, Karin Monnier-Jobe, Kabula Ciamala, Michael Knorr and Carsten Strohmann

Affiliation:

Keywords: [4+2] Cycloaddition, regiochemistry, pyrroles, spiro-compounds, 3-aryliden-4-chromanones, Reissert salt

Abstract: Synthesis of several spiro[4-aryl-5-hydroxy-2-(1-isoquinolinyl)-5-phenyl-4,5-dihydro-3H-pyrrole- 3,3-3H-chroman-4-ones] has been accomplished in satisfying yields by regioselective [4+2] cycloaddition reaction of a 2-benzoyl-1,2-dihydroisoquinoline-1-carbonitrile tetrafluoroborate salt across (E)-3-arylidene-4- chromanones. The spirocompounds evolve to pyrroles after acidic hydrolysis. The crystal structure of (10c) has been determined by an X-Ray study diffraction.

Cite this article as:

Askri Moheddine, Rammah Mohamed, Monnier-Jobe Karin, Ciamala Kabula, Knorr Michael and Strohmann Carsten, Synthesis of Some Spirochroman-4-Ones by Regioselective [4+2] Cycloaddition Reactions, Letters in Organic Chemistry 2007; 4 (3) . https://dx.doi.org/10.2174/157017807780737255