546
I. Osaka
N
S
N
N
S
N
S
S
R
R
NTz2T
O
O
N
S
N
S
S
N
S
N
S
S
N
N
R
R
R
R
NaBH 4
(20 eq)
CoCl 2 .6H 2 O
(5 mol%)
THF/EtOH
H 2 N
NH 2
N
Se
N
N
S
N
S
S
R
R
SeOCl 2
Pyridine
/Chloroform
N
Se
N
N
Se
N
S
S
R
R
NSz2T
O
O
N
Se
N
S
S
R
R
NaBH4
(20 eq)
CoCl 2 .6H 2 O
(5 mol%)
THF/EtOH
SOCl2
Pyridine/
Chloroform
H 2 N
NH2
N
Se
N
S
S
N
N
R
R
N
O
N
N
O
N
S
S
R
R
NOz2T
O
O
N
O
N
S
S
N
O
N
S
S
N
N
R
R
R
R
NaBH 4
(20 eq)
CoCl 2 .6H 2 O
(5 mol%)
THF/EtOH
N
S
N
N
O
N
S
S
R
R
Pyridine/Chloroform
H 2 N
NH 2
SOCl 2
Pyridine/Chloroform
N
Se
N
N
O
N
S
S
R
R
SeOCl 2
NTP2T
90%
90%
92%
92%
NTS2T
NSP2T
71%
80%
71%
NOP2T
NOT2T
NOS2T
Scheme 15.3 Synthesis of hybrid naphthalene-based nitrogen-containing heteroaromatics