原甲酸三乙酯

O
EtMgBr
Et2O
O
benzene
O C CH O C C CH OEt OEt
OH OEt EtO C H OEt HO HO
OH
OEt CH OEt
AlCl3
CH2Cl2
EtO OEt EtO C H OEt CHO H N CH
OEt
CH(OEt)3 24h heated
N
CHO
CHO OEt EtO C H OEt HN
O
NH2
8-10 h rf
H2N
N
O
O
N
N
N OEt EtO C H OEt H N C H2 H2 C N H
NH4Cl 1100c 90min
N
OEt EtO C H OEt
N
S
O C NHPh
N
Ac2O 4h
S
O
N N
Ph
NH2
O OEt OH EtO C H OEt NH2 H2N Ph
O
p-MePhSO3H 15h rt
N
N
Ph
O OEt H2N EtO C H OEt O S
NH2
H N
N
450C 1h
N S O O
上乙氧甲叉基
具有强吸电子的亚甲基
OEt EtO C H OEt CN CN
Ac2O 3-4h rf
NC C H OEt
NC
OEt EtO C H OEt
COOEt
ZnCl2 Ac2O 13h rf
N N N OEt
OEt EtO C H
AcOH 2h
CH3
CH3
OEt EtO C H OEt
Br
Br NaN3 N NH2 H2O N N N N N
AcOH 4-5 h
HN OEt EtO C H OEt N H N NH
3-18 h
NH2
N DMF
rf
N N N NH2
O OEt EtO C H OEt O O N NH2 CN H2N
EtOH
OEt OEt EtO C H OEt NC CHO CH OEt
NBS rt
EtOH
NC
OEt OEt EtO C H OEt EtOH O CHO NH4Cl O CH OEt
OEt EtO C H OEt
O
OEt CH3OH cyclohexane InCl3 rf 12 h OEt
EtOOC C H OEt
COOEt
EtOOC
OH O
OEt EtO C H OEt CH3
HClO4 Et2O
HO OH O
O
O S OEt EtO C H OEt O N H N Ph N N
O S N N N O N H Ph
Ac2O 5h rf
HC EtO
CH3 N NH2 OEt EtO C H OEt OH N O N NH O N N OH CH NH N N O O N NH
Ph O EtO OEt EtO C H OEt S Ac2O rf NHPh S H C
Ph O
NHPh
乙基化
O OEt EtO C H OEt OEt
CF3COOH
OEt EtO C H OEt
N S S
BF3-Et2O CHCl3 rf 1h
N C+ SEt S
-
FF B3+ FF-
O OEt EtO C H OEt HO
O
O
O
EtOH rf
OH EtO OEt
OEt EtO C H OEt
O
O P OCH3 OCH3
OEt
O P OCH3 OCH3
FeCl3
CH2 OEt EtO C H OEt PO3H2
CH2
rf
O OEt OEt P
缩醛
OEt OEt EtO C H OEt CHO CH OEt
DDQ 5h
原甲酸三乙酯
罗炼
• • • •
1 上乙氧甲叉基 2 羟基乙基化 3 缩醛缩酮 4 其他
1 上乙氧甲叉基
在氨基上乙氧甲叉基
OEt EtO C H OEt NH2 NH2 N
8' 850c
N H
NH2 HO OEt EtO C H OEt N H N
N
2h rf
O
N
N H
H N OEt EtO C H OEt Ph CN NH2
O OEt EtO C H OEt EtOH Bu4N+Br3-
OEt CH3 OEt
O OEt EtO C H OEt O OEt
p-MePhSO3H py
benzene
OEt OEt OEt O
其他
OEt EtO C H OEt Ph C CH
ZnI2
Ph
C
C
CH
OEt OEtຫໍສະໝຸດ OEt EtO C H OEt
H N
NH3 MeOH
Ph CN
N
NH2
O OEt EtO C H OEt NH2 Cl NH N Cl
O N N
rf
N
NH OEt EtO C H OEt O N H S H2N N N
N
CH3COOH 10-60min 800c
O
N S
N H
H2N EtO OEt O
S
S N NaN3 H2O O
H2NCHO
H2SO4
OHC
H N
C H
NH CHO
O HN N N NH2 O HN N NH2 C OEt HN NH2 CN HN C OH HN N N
O C OEt OEt CH O
N N N
NH2