synthesis of various substituted naphthalene via palladium catalyzed cyclization
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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. - PowerPoint PPT PresentationTRANSCRIPT
NHCOCH3
C5H11
C5H11
C5H11
OHN
O
CH3
ONH
O
H3C
Reagent Solvent Temp. Time Yields
Pd(CH3CN)2Cl2 CH3CN
CH3CN
THF
DMF
DMF
NMP
NMP
DMSO
80
RT
80
RT
80
RT
80
RT
48
2
48
2
48
2
48
8
18
18
48
48
33
48
18
1 2
DMSO 80 2 17
THF 48
12
RT
2
Pd(CH3CN)2Cl2
Solvent
Pd(OAc)2
Pd(PPh3)2Cl2
PdCl2
NHCOCH3
C5H11
C5H11
C5H11
OHN
O
CH3
ONH
O
H3C
Reagent Yields(%)
DMFheat to 80oC
Pd(II)
1 2
16
19
15
NH
R
R
R
OHN
O
R'O
NHO
R'
DMF
Pd(CH3CN)2Cl2
R
1d R = Ph
Yields(%)
2d ( 35 )
R'
CH3
Ph 1e R = C5H11
1g R = Ph
2e ( 26 )
2g ( 22 )
heat to 80oCR'
O
1b R = C6H13
1c R = C7H15
1f R = C6H13
1 2
2b ( 38 )
2c ( 36 )
2f ( 24 )
NH
R
O Pd(CH3CN)2Cl2
NH
R
O
NH
O
Pd Pd
R
HNO
RPd
NHO
RPd
OHN
OO
NHO R
R
HN
OH2O
1 3 4
5
8
2
HNO
NHO
PdR R
Pd
6
HNO
NHO
PdR R
Pd
7
H2O
R
PdR
OHN
O
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: 886-7-3121101 ext 2220; Fax: 886-7-3125339; E-mail: [email protected]
AbstractA 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.
NHR'
R
R
R
ONHR'O
R'HN
12
Pd(CH3CN)2Cl2
DMF, heat 80oC
Table 1 Reaction of 1 with Pd(CH3CN)2Cl2 in Various Solvents
Table 2 Reaction of 1 with Various Pd(II)-catalysts
Table 3 Cyclization of enediynes 1b-g
Figure 1 X-ray structure of compound 2d
Scheme 1 Proposed Mechanism for the Formation of compound 2