Abstract
The easily accessible 2-(chloroseleno)benzoyl chloride has broad application in the synthesis of benzizoselenazol-3(2H)-ones and benzo[b]selenophen-3(2H)-ones. Treatment of 2-acylbenzo[b]selenophen-3(2H)-ones with nitrogen nucleophiles such as hydrazines and hydroxylamine resulted in formation of 2-substituted 3-hydroxybenzo[b]selenophenes in 72–98% yield.
ACKNOWLEDGMENT
The work was supported by the Ministry of Science and Higher Education (Grant 351788/20305).
Notes
b
Yields of 7 with MeNHNH2 as reagent.
c
Yields of 7 with PhNHNH2 as reagent.
d
Yields of 7 with NH2OH as reagent.
Kloc
,
K.
;
Osajda
,
M.
;
Młochowski
,
J.
2-(Chloroseleno)benzoyl chloride: A tandem reagent for selenenylation–acylation of C-H acids
.
Chem. Lett.
2001
,
30
,
826
–
827
.
Kloc
,
K.
;
Młochowski
,
J.
Selenenylation–acylation of ketones with 2-chloroselenobenzoyl chloride: A novel route to benzo[b]selenophenes
.
Tetrahedron Lett.
2001
,
42
,
4899
–
4902
.
Kloc
,
K.
;
Osajda
,
M.
;
Młochowski
,
J.
2-(Chloroseleno)benzoyl chloride: A tandem reagent for selenenylation–acylation of C-H acids
.
Chem. Lett.
2001
,
30
,
826
–
827
.
Kloc
,
K.
;
Osajda
,
M.
;
Młochowski
,
J.
2-(Chloroseleno)benzoyl chloride: A tandem reagent for selenenylation–acylation of C-H acids
.
Chem. Lett.
2001
,
30
,
826
–
827
.
Kloc
,
K.
;
Osajda
,
M.
;
Młochowski
,
J.
2-(Chloroseleno)benzoyl chloride: A tandem reagent for selenenylation–acylation of C-H acids
.
Chem. Lett.
2001
,
30
,
826
–
827
.
Kloc
,
K.
;
Osajda
,
M.
;
Młochowski
,
J.
2-(Chloroseleno)benzoyl chloride: A tandem reagent for selenenylation–acylation of C-H acids
.
Chem. Lett.
2001
,
30
,
826
–
827
.
Kloc
,
K.
;
Młochowski
,
J.
Selenenylation–acylation of ketones with 2-chloroselenobenzoyl chloride: A novel route to benzo[b]selenophenes
.
Tetrahedron Lett.
2001
,
42
,
4899
–
4902
.