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

Authors: Askri, Moheddine; Rammah, Mohamed; Monnier-Jobe, Karin; Ciamala, Kabula; Knorr, Michael; Strohmann, Carsten

Source: Letters in Organic Chemistry, Volume 4, Number 3, April 2007 , pp. 222-227(6)

Publisher: Bentham Science Publishers

Buy & download fulltext article:

Price: $63.10 plus tax (Refund Policy)

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.

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

Document Type: Research article

DOI: http://dx.doi.org/10.2174/157017807780737255

Publication date: 2007-04-01

More about this publication?

Letters in Organic Chemistry publishes original letters on all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is placed on publishing quality papers very rapidly. Letters are processed rapidly and take full advantage of the Internet technology both for the submission and the review of the manuscripts.
The journal is essential reading for all organic chemists both in academia and industry.