Synthesis of naphthalenes through three-component coupling of alkynes, Fischer carbene complexes, and benzaldehyde hydrazones via isoindole intermediates.
The synthesis of naphthalene derivatives through three-component coupling of 2-alkynylbenzaldehyde hydrazones with carbene complexes and electron-deficient alkynes has been examined. The reaction involves formation of an isoindole derivative, followed by intramolecular Diels-Alder reaction, followed by nitrene extrusion. The reaction was highly regioselective using unsymmetrical alkynes.
Duan
Shaofeng
S
Department of Chemistry & Biochemistry, New Mexico State University, MSC 3C, Las Cruces, NM 88003-8001, USA.
Sinha-Mahapatra
Dilip K
DK
Herndon
James W
JW
D000480:Alkynes / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry*; D006835:Hydrazones / Q000737:chemistry*; D054833:Isoindoles / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D009281:Naphthalenes / Q000138:chemical synthesis*
D000480:Alkynes; D001547:Benzaldehydes; D006835:Hydrazones; D054833:Isoindoles; D009281:Naphthalenes; C030011:carbene; D008697:Methane; C032175:benzaldehyde