Đ xu t cơ ch cho các ph n ng Check Box

B001
NaOH
Na2HPO4
CHO HO2C
(pH 2.5-4.5)
+ MeNH2 + O MeN O
CHO HO2C H2O,

B002
O OH
Al(i-OPr)3

i-PrOH
reflux;
aq HCl

B003
O NH2NH2 OH
AcOH (cat)
O EtOH, rt

B004
1) aqH2O2, K2CO3 O i-Pr
MeOH, 0 oC to rt Ar =
2) ArSO2NHNH2
O CH2Cl2-AcOT, rt i-Pr i-Pr
aq K2CO3

B005
O
CHO NaCN (cat)
CN
+ CN DMF
N 35 oC N

B006
Me Bn
Cl N
H
Me
HO S O
O
(cat)
+ Me Me
Et3N, EtOH O
O 80 oC

Me
 Check Box
B007
1) KOAc, Ac2O
reflux
H
O 2) aq HCl, reflux O CO2H
O

B008
O
O N O
Me
Me Me H aq HCl

KOH (cat) benzene

O MeOH, reflux reflux O

B009
O O
LiOMe
H + MeO2C CO2Me OMe
MeOH
reflux CO2H

B010
Me O H2C N N Me O

Ph OH Et2O, rt Ph OMe

B011
OTs
Li
liq NH3
O O

B012
CN NaNH2

liq NH3
Cl -78 oC CN
 Check Box
B013
NaNO2
NH2 aq HCl, 0 oC Cl

CuCl2 (trace CuCl)

0 oC to rt

B014

DCC, TFA O
Me pyridine Me
OH H
Me DMSO, rt Me

B015
HO aq HBr

H2O, 0 oC
Br

B016
OTs
H
t-BuOK
t-BuOH
OH 40 oC O

B017
n-Bu3SnH
Me Me H Me
AIBN (cat)
Me Me Me
I benzene
reflux H H

B018
O O

Ph O O Ph CCl3
(cat)

CHCl3, reflux
 Check Box
B019
O Cl

Cl O Me
o
Ph CH2Cl2, -7 C
N NH HCl
MeOH, reflux

B020
O OMe
Me3SiI H
C5H11 N CH2Cl2, reflux C5H11 N
CO2Me CO2Me
MeOH, rt

B021
EtO2C O Pd(dba)2, (cat) EtO2C
dppb, Et2NH
N O NH
THF, rt

B022
Ph

O O NO2 PhSH
S KOH
N N Ph
CH3CN H
50 oC MeO

MeO

B023
O O
BF3-Et2O CHO
O Me
Me benzene
Me
Me Me Me
B024
O Me
O Me S N O
O NO

aq KOH, EtOH
10 to 20 oC
 Check Box
B025

NC NC
Me
Me
Me o-dichlorobenzene HMe
180 oC

B026
O O
FeCl3

CH2Cl2
SiMe3 0 oC H

B034
1) O2, hv OH
acetone

2) Et3N, CH2Cl2
reflux
O

B035
1) O2, hv
acetone O

2) Ph3P
benzene

B041
PhCHO OH
CrCl2 (2 eq)
Me Br Ph
THF,
o
Me
0 C to rt

B042
H2, CO CHO
HRhCO(PPh3)2 (cat)
CHO +
n-Bu n-Bu n-Bu Me
benzene, rt
 Check Box
B045

O KSCN S
H Ph
Ph dioxane-H2O H
60 oC

B046
O O
Me2NH (1.1 eq)
Me Me
MeOH
MeO OMe Me2N

B047
1) Me2NCH(OMe)2
OBn pyrrolidine OBn
Me DMF, 110 oC

2) Raney Ni, NH2NH2

NO2 THF-MeOH N
H
rt to 50 oC

B048
O O
S NC

Me
O (TosMIC) CN
t-BuOH, EtOH
DME
5 to 40 oC

B049
1) CBr4 (1 eq)
Ph3P (2 eq)
O CH2Cl2, 0 oC
n-C7H15 H
n-C7H15 H
2) n-BuLi (2 eq)
THF, -78 oCto rt
H2O
 Check Box

B050
1) ArSO2NHNH2 Ph Ph
Me HCl, MeCN, rt Me i-Pr
O
Me Me OH Ar =
2) n-BuLi (2.2 eq)
THF, -78 oC to rt i-Pr i-Pr
Me Me Me Me
benzophenone
0 oC to rt

B051
O
MeO CO2Na
HO CO2Me

MeO AcOH NH
HO
+ MeOH-H2O OMe
HO CO2Me 35 oC
OMe
NH2
HO

B052

(HCHO)n
O O K2CO3 O O OH
H
MeOH OH
O reflux

B053
N

N
CO2Me O OH
(DABCO, cat)
+ Me Me CO2Me
H heat, rt

B054

N
H 1) aq HCl O
O TsOH CO2Me 60 oC CO2Me
xylene Et2O, rt 2) H2, Pd/Al2O3
reflux MeOH, rt
 Check Box
B055
O
Me S N3
O
O O Et3N O O

Ph OEt Ph OEt
MeCN
rt N2

B056
1) t-BuOK
Ts EtOH-toluene
N O
0 oC to rt H3N
2) aq HCl, rt Cl
S S

B057
Me Br2 Me
NaHCO3 NaOEt
CO2Et
Et2O, 0oC EtOH-Et2O
O reflux

B058
KOH
O O
I2 DMF, 60 oC

CO2Me MeCN-H2O MeI, rt

rt O O OMe

B059

H2C N N , 2 eq
O Et2O, rt O
MeO2C MeO2C Br
Cl HBr
B060

CO2H Ac2O
reflux
N N O
Me Me
 Check Box

B061
O
EtO P
EtO CN H
Me OH + H2N CO2t-Bu Me N CO2t-Bu
11 Et3N 11
Me OH O DMF, rt Me OH O

B062
O
PCl5 CN
NH2
POCl3
N 100 oC N Cl
O

B063
O O
DDQ
Me Me
OH OMe CH2Cl2 O

OMe

B064
O
1)
Cl S N C O
O (CSI) CN
OMe toluene, rt OMe

2) DMF, rt

OMe OMe

B065
NC
O
CO2H Br
N
t-BuNO, H2O H
NH2 Br
ClCH2CH2Cl
reflux
 Check Box

B066

OH
1) PhI(OAc)2
H
CF3CH2OH
O CO2Me
2) NaHCO3 N
MeOH O
OH H Cbz
NHCbz

B067

MeO2C
OH
DBU (cat) Me
Cl3CCN TfOH (cat) MeO2C
OH OBn
CH2Cl2 cyclohexane Me
CH2Cl2, rt

B068

t-BuOH, HCO2H
H2SO4

CCl4, rt CO2H

B069

n-BuLi Ph
Ph O Ph Ph
Et2O, rt
OH

B070

OH
Ph N
NaH Ph
Ph CO2Me CO2Me
DMF-dioxane O
rt
 Check Box

B071
S
N
N n-Bu3SnH
O H Me
AIBN (cat)
O
benzene, reflux
OH
Me

B072

O O
S Br
Br Br
Me hv Me t-BuOK

CH2Cl2, -15 oC t-BuOH-THF

SO2CH2Br 0 oC to rt
H

B073
KNH2
Me Me Br hv Me
+
O THF, rt O

B074

S Bu
O hv N
N Bu BF3-Et2O N
O N S
THF, rt

B075
1) CHBr3, t-BuOK
petroleum ether
Me 0 oC to rt Me

2) MeLi
Me Me
Et2O, 0 oC to rt
 Check Box
B076
O

Cl3C OEt Cl

NaOMe
Cl
petroleum ether
0 oC to rt

B077
1) Cl3CCO2H, Cl3CCO2Na
DMF, rt; Ac2O, rt
Zn, AcOH, 60 oC
CHO
2) MeLi, THF, -10 oC
H3O+

B078
BnNH2
aq HCHO
OH
TFA
SiMe3
H2O, 25 oC NBn
H

B079
O
Me Me O Me Me
S
Me HN NH2 Me
H Me H Me
NO2
Me H Me H
EtO2C N N CO2Et
H H H H
Ph3P, NMM
HO -30 oC to rt H

B080
1) Ph3P CHCO2Et
CHO benzene, reflux

NO2 2) (EtO)3P N CO2Et

170 oC H
 Check Box
B081

H2N CO2H NaNO2 Cl CO2H

H aq HCl H
Me Me
rt

B082

MeO NaNO2
A
aq HCl, 0 oC
NH2

1) KOH, EtOH-H2O
A
O 0 oC MeO Me
CO2Et
Me 2) aq HCl, EtOH
Et N CO2Et
65 oC H

B083

O (C6H13)3B O
N2 C6H13
Ph THF-H2O Ph
reflux

B084
O I2, AgNO3
HC(OMe)3 OMe
Me
MeOH O
i-Bu reflux; i-Bu
H2O

B085
Me Me Me Me
H2SO4

Ac2O
Me -20 oC to rt
O O
SO3H
 Check Box
B086

OMs
Me B2H6, THF

aq NaOH Me
reflux

B087
1) Br2, CHCl3-CH2Cl2 Me
Me
0 oC
O O
2) t-BuOK, Et2O
Me 65 oC Me

B088

N
N H
+
N N toluene
O MS 4A N
reflux

B089
OH
N aq NaOCl N O
Et3N
H +
CH2Cl2
0 oC

B090
PhN C O (2eq)
N Me
Et3N O
O2N Me + AcO
benzene
AcO
rt to 80 oC

B091
CH3C(OMe)3
Me Me
EtCO2H (cat)
EtO2C
HO 138 oC
Me Me
 Check Box
B092
O
PhCHO Me
Me CSA
N Ph
H Me OMe benzene N
reflux

Me

B093
1) TBSOTf , Et3N
O CH2Cl2
-78 to 0 oC HO2C OMe
O
2) toluene, 110 oC;
1 N HCl, THF, rt
OMe

B094
O
S
Ph
Me NaH
CHO
THF decalin Me
rt 150 oC
OH

B095
1) 1,3-dithiane, 20 oC
2) n-BuLi, THF
-78 oC
Br
3) HgCl2, MeCN-H2O
reflux CHO

B096

Br H CO2Et
Me
N CO2Et N
CHO K2CO3 Me H
DMF toluene
OH H
20 oC reflux
Dean-Stark trap O
 Check Box

B097

1) NaOCl, pyridine NOH

Me
AcO -78 oC AcO

Me 2) hv , benzene, rt Me
AcO AcO
H 3) THF-i-PrOH H
Me OH Me OH
OAc reflux OAc

B098
O NO2
hv O
Ph O
Ph OH
CCl4, rt

B099
O
Me P(OEt)2
O O n-BuLi Me O
THF
-78 oC

B100

PPh3 Br
NaH
CHO
N Et2O N
H reflux

B101
N3 H
Ph3P N
Ph H H
Ph
OH toluene Ph Ph
reflux
 Check Box

B102
Ph3P Se
H O H TFA
Ph Ph Ph Ph
CH2Cl2, rt

B103
S
1)
N N N N
HO OH toluene, reflux

Ph Ph 2) (MeO)3P Ph Ph
reflux

B104

O Me3SiI (2 eq)
C8H17 C8H17 CCl4, rt C8H17 C8H17

B105

OMOM 1) Pt[(H2C=CHSiMe2)2O]2 OMOM

C6H13 toluene, 60 oC C6H13
O H 2) 30% H2O2, aq KOH
Si OH OH
Me Me MeOH-THF, rt

B106

Me Me PhSCl Me Me
Me Et3N
OH
CH2Cl2
Me -78 oC to rt Me
Me
SPh
O
 Check Box
B107
O Me
HO
SmI2 (4 eq)
MeO I
Me THF-HMPA O
O 0 oC to rt Me

B108
MeO OMe MeO OMe
Me Hg(OTf )2 (1% mol) Me

MeNO2
0 oC H
Me
Me

B109
PCy3
Cl
Ru
Cl
PCy3 Ph MeO2C
O (cat) O
MeO2C H N
CH2Cl2 H
reflux

B110

SMe2 I
NaH NaN3
CHO N3
N o
THF, 0 C H2O, 0 C o N
H
OH
B111
O Ph
TfOH
N (n = 1)
Me
CH2Cl2
O N3 0 oC
O
Me n Ph TfOH
Me (n = 3)
CH2Cl2
0 oC NHPh
 Check Box

B112
O O O O
S S
N Tol S S Tol O
Et3N aq HCl S

MeCN, reflux 50 oC S

B113
Ph
t-BuOK
O PhCHO O
AcN HN
NAc t-BuOH-DMF NAc
O rt O

B114
O

Me
Me
N
OH CSA (0.1 eq)
Me

CO2H THF, 0 oC toluene O

reflux
O

B115
Na (4eq)
CO2Et Me3SiCl (4 eq) OSiMe3

toluene
CO2Et reflux OSiMe3

B116
O3
MeOH-CH2Cl2
-78 oC;
TsOH
-78 oC to rt OMe

NaHCO3 MeO CHO

(neutralize);
Me2S
 Check Box
B117
O3
M OH-CH2Cl2
e
-78 oC; OMe

evaporation; O CHO
Ac2O, Et3N
0 oC

B118
OEt n-Bu3SnCl (cat)
I NaBH3CN OEt
O AIBN, t-BuNC O

t-BuOH, reflux

CN

B119
O
N3 BF3-Et2O N O

CH2Cl2, rt

B120

Ph O
NMO, Et3N
NOH N Ph
Cl CH2Cl2 O
rt

B121
O O

decalin
290 oC
 Check Box

B122
Me Me 1) CH2N2, Et3N Me Me
Et2O, 0 oC

2) 95 oC
O O
SO2Cl

B123

PPh3Br
O
t-BuOK

THF, rt

B124
1) CHCl3, reflux
OTBS
2) PhSeCl, CH2Cl2 Me
O -78 oC
O
Me 3) aq H2O2, THF
0 oC H

B125
1) ClCH2COPh, K2CO3
THF, rt
S
Ph SH
2) hv , cyclopentadiene
Ph
CH2Cl2, rt

B126

Me O Me
Me rhodium(II) mandelate
AcO
N2 CH2Cl2
AcO reflux Me O
 Check Box

B127
Cr(CO)5 OMe
Ph Ph Ph
OMe
n-Bu2O Cr(CO)3
Ph
45 oC
OH

B128
Ti(Oi-Pr)4 (cat)
O EtMgBr (2 eq) Me OH
Me OMe Et2O, rt