Novel Synthesis of Isoquinolines Using Isobenzofuran-Nitrile Diels-Alder Reactions
(Equation presented) The synthesis of isoquinolines through coupling of 2-alkynylbenzaldehyde derivatives with β-cyanocarbene complexes has been examined. The reaction involves formation of an isobenzofuran followed by intramolecular Diels-Alder reaction with the nitrite, 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.
Coupling of β-cyanocarbene-chromium complexes with 2-alkynylbenzoyl derivatives: A [5+5]-cycloaddition approach to phenanthridines
The coupling of β-cyanocarbene complexes and 2-alkynylbenzoyl derivatives has been examined. The reaction afforded phenanthridine derivatives in a complex tandem process involving carbene-alkyne coupling, isobenzofuran formation, intramolecular Diels-Alder reaction using a nitrile dienophile, and deoxygenation. The chemistry could not be reproduced in non-chromium-based systems. Georg Thieme Verlag Stuttgart.
Ghorai, Binay K.,Duan, Shaofeng,Jiang, Delu,Herndon, James W.
p. 3661 - 3669
(2008/03/13)
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