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.
Ghorai
Binay K
BK
Department of Chemistry and Biochemistry, New Mexico State University, MSC 3C, Las Cruces, New Mexico 88003, USA.
Jiang
Delu
D
Herndon
James W
JW
D001572:Benzofurans / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis*; D009570:Nitriles / Q000737:chemistry*
D001572:Benzofurans; D007546:Isoquinolines; D009570:Nitriles; C105430:benzofuran