Synthesis of various substituted naphthalene via Palladium catalyzed Cyclization

1
Synthesis of various substituted naphthalene via
Palladium catalyzed Cyclization Chia-Ying Lee b,
Ming-Jung Wu a a Faculty of Medicinal and
Applied Chemistry, Kaohsiung Medical University,
Kaohsiung, Taiwan. b Graduate Institute of
Pharmaceutical Sciences, Kaohsiung Medical
University, Kaohsiung, Taiwan. Tel [phone]
ext 2220 Fax [phone] E-mail
mijuwu_at_cc.kmu.edu.tw
Abstract A novel palladium catalyzed cyclization
of enediynes to give the naphthalene derivatives
was reported. For instance, treatment of
N-acetyl-2-(3(Z)-undecen-1,5-diynyl)anilines 1
with Pd(CH3CN)2Cl2 in DMF at 80 oC for 2h in 48
yield.
Table 1 Reaction of 1 with Pd(CH3CN)2Cl2 in
Various Solvents
Table 3 Cyclization of enediynes 1b-g
Table 2 Reaction of 1 with Various
Pd(II)-catalysts
Scheme 1 Proposed Mechanism for the Formation of
compound 2
Figure 1 X-ray structure of compound 2d