Abstract
Practicable and concise syntheses of 6-chloro-7,8,9,14-tetrahydroquinolino[2′,3′:7,6]cyclohept[b]indoles by two routes are described. Both commenced with 1-oxo-2,3,4,5,10-hexahydrocyclohept[b]indoles and utilised either the acid-catalysed condensation with 2-aminobenzonitrile, followed by treatment with POCl3 or, better, direct condensation of the ketone with anthranilic acid in POCl3.
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References
1.
Merlic
C.A.
,
Motamed
S.
,
Quinn
B.
, J. Org. Chem. , 1995 , 60 , 3365 .
2.
Malapel Andrieu
B.
,
Merour
J. Y.
, Tetrahedron , 1998 , 54 , 11095 .
3.
Radchenko
O.S.
,
Novikov
V. L.
,
Elyakov
G. B.
, Tetrahedron Lett. , 1997 , 38 , 5339 .
4.
Abouabdellah
A.
,
Dodd
R. H.
, Tetrahedron Lett. , 1998 , 39 , 2119 .
5.
Abas
S.A.
,
Hossain
M. B.
,
Vanderhelm
D.
,
Schmitz
F. J.
, J. Org. Chem. , 1996 , 61 , 2709 .
6.
Balamurali
R.
, and
Rajendra Prasad
K. J.
, IL Farmaco , 2001 , 56 , 239 .
7.
Rice
L.M.
,
Hertz
E.
,
Freed
M. E.
, J. Med. Chem. , 1964 , 7 , 313 .
8.
Carelli
V.
,
Marchini
P.
,
Moracci
F. M.
, and
Liso
G.
, Tetrahedron Lett. , 1967 , 8 , 3427 .
9.
Perkin
W.H.
, and
Plant
S. G. P.
, J. Chem. Soc. , 1928 , 2583 .
10.
Kavitha
C.
,
Rajendra Prasad
K. J.
, Heterocycl. Commun. , 1999 , 5 , 481 .
11.
Gribble
G.W.
, J. Chem. Soc. Perkins Trans. 1 , 2000 , 1045 .
12.
Knolker
H-J.
,
Reddy
K. R.
, Chem. Rev. , 2002 , 102 , 4303 .
13.
Kawasaki
T.
,
Higuchi
K.
, Nat. Prod. Rep. , 2005 , 22 , 761 .
14.
Bennasar
M.L.
,
Vidal
B.
,
Bosch
J.
, J. Am. Chem. Soc. , 1993 , 115 , 5340 .
15.
Bennasar
M.L.
,
Vidal
B.
,
Bosch
J.
, J. Org. Chem. , 1997 , 62 , 3597 .
16.
Bennasar
M.L.
,
Vidal
B.
,
Kumar
R.
,
Lasaro
A.
,
Bosch
J.
, Eur. J. Org. Chem. , 2000 , 3919 .
17.
Bennasar
M.L.
,
Vidal
B.
,
Lazaro
A.
,
Kumar
R.
,
Bosch
J.
, Tetrahedron Lett. , 1996 , 37 , 3541 .
18.
Bennasar
M.L.
,
Zulaica
E.
,
Juan
C.
,
Llauger
L.
,
Bosch
J.
, Tetrahedron Lett. , 1999 , 40 , 3961 .
19.
Bennasar
M.L.
,
Zulaica
E.
,
Sole
D.
,
Alonso
A.
, Synlett , 2008 , 667 .
20.
Yamuna
E.
,
Sridharan
M.
,
Rajendra Prasad
K. J.
,
Zeller
M.
, J. Chem. Crystallogr. 2010 , 40 , 402 .
21.
Benoit
J.
,
Routier
S.
,
Merour
J. Y.
,
Colson
P.
,
Hoursier
C.
,
Bailly
C.
, Anticancer Res. , 2000 , 20 , 3307 .
22.
Clivio
P.
,
Richard
B.
,
Nuzillard
J. M.
,
Zeches-Hanrot
M.
, Phytochemistry , 1995 , 40 , 987 .
23.
Fehenel
E.A.
, J. Org. Chem. , 1966 , 31 , 2899 .
24.
Borsche
W.
,
Sinn
F.
, Leibigs Ann. Chem. , 1939 , 538 , 283 .