Novel synthesis of isoquinolines using isobenzofuran-nitrile Diels-Alder reactions.
[reaction: see text] The synthesis of isoquinolines through coupling of 2-alkynylbenzaldehyde derivatives with beta-cyanocarbene complexes has been examined. The reaction involves formation of an isobenzofuran followed by intramolecular Diels-Alder reaction with the nitrile, a process with limited precedent. The unique success of this process in this system has been attributed to deoxygenation of the initial adduct to form the isoquinoline ring system.
Department of Chemistry and Biochemistry, New Mexico State University, MSC 3C, Las Cruces, New Mexico 88003, USA.
Binay K
BK
Ghorai
Delu
D
Jiang
James W
JW
Herndon
D001572:Benzofurans / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis*; D009570:Nitriles / Q000737:chemistry*
D001572:Benzofurans; D007546:Isoquinolines; D009570:Nitriles; C105430:benzofuran