Abstract
Triazolo-thieno[3,2-e]pyrimidines obtained by cyclisation of 4-hydrazino-2-(methylthio)thieno[2,3-d]pyrimidine with formic acid, acetic acid, cyanogen bromide and carbon disulfide, and by oxidation of the derived aldehyde hydrazones, are found to be the triazolo[4,3-c] isomers. These [4,3-c] compounds resist isomerisation in acid, but they undergo Dimroth rearrangement to the [1,5-c] isomers under basic conditions. The crystal structure of one such rearranged product, 5-methoxy-8,9,10,11-tetrahydro[1]benzothieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine (
References
1.
Gillespie
E.
,
Dungan
K.W.
,
Gomol
A.W.
, and
Seidehamel
R.J.
, Int. J. Immunopharmacol. , 1985 , 7 , 655 .
2.
Gomol
A.W.
, and
Temple
D.L.
, Drug Dev. Res. , 1987 , 10 , 57 .
3.
Shishoo
C.J.
,
Shirsath
V.S.
,
Rathod
I.S.
, and
Yande
V.D.
, Eur. J. Med. Chem. , 2000 , 35 , 351 .
4.
Shishoo
C.J.
,
Shirsath
V.S.
,
Rathod
I.S.
,
Patil
M.J.
, and
Bhargava
S.S.
, Arzneim. Forsch. , 2001 , 51 , 221 .
5.
Unverferth
K.
, Pharmazie , 1990 , 45 , 545 .
6.
Russel
P.K.
,
Press
J.B.
,
Rampulla
R.A.
,
McNally
J.J.
,
Falotico
R.
,
Keiser
J.A.
,
Bright
D.A.
, and
Tobia
A.
, J. Med. Chem. , 1988 , 31 , 1786 .
7.
Cannito
A.
,
Perrssin
M.
,
Luu Duc
C.
,
Huguet
F.
,
Gaultier
C.
, and
Narcisse
G.
, Eur. J. Med. Chem. , 1990 , 25 , 635 .
8.
Santagati
A.
,
Modica
M.
,
Santagati
M.
,
Caruso
A.
, and
Cutuli
V.
, Pharmazie , 1994 , 49 , 64 .
9.
Patil
C.D.
,
Sadana
G.S.
, and
Deadhar
K.D.
, J. Indian Chem. Soc. , 1991 , 68 , 169 .
10.
El-Bahaie
S.
, and
Assy
M.G.
, Pharmazie , 1990 , 45 , 216 .
11.
Nasr
M.N.
, and
Gineinnah
M.M.
, Arch. Pharm. , 2002 , 335 , 289 .
12.
Sasaki
S.
,
Cho
N.
,
Nara
Y.
,
Harada
M.
,
Endo
S.
,
Suzuki
N.
,
Furuya
S.
, and
Fujino
M.
, J. Med. Chem. , 2003 , 46 , 113 .
13.
Patil
V.D.
,
Vise
D.S.
,
Worting
L.L.
,
Bloomer
R.C.
, and
Townsend
L.B.
, J. Med. Chem. , 1985 , 28 , 423 .
14.
Ram
V.J.
,
Pandey
H.K.
, and
Vietinek
A.J.
, J. Heterocycl. Chem. , 1981 , 18 , 1277 .
15.
Dickinson
R.P.
,
Bell
A.W.
,
Hitchcock
C.A.
,
Narayana-Swami
S.
,
Ray
S.J.
,
Richardson
K.
, and
Troke
P.F.
, Bioorg. Med. Chem. Lett. , 1996 , 6 , 2031 .
16.
Ulusoy
N.
,
Gursoy
A.
, and
Otuk
G.
, Farmaco , 2001 , 56 , 947 .
17.
Palaska
E.
,
Sahin
G.
,
Kelicen
P.
,
Durlu
N.T.
, and
Altinok
G.
, Farmaco , 2002 , 57 , 101 .
18.
El-Sherbeny
M.A.
,
El-Ashmawy
M.B.
,
El-Subbagh
H.I.
,
El-Emam
A.A.
, and
Badria
F.A.
, Eur. J. Med. Chem. , 1995 , 30 , 445 .
19.
Santagati
M.
,
Modica
M.
,
Santagati
A.
,
Russo
F.
, and
Spampinato
S.
, Pharmazie , 1996 , 51 , 7 .
20.
Brown
D.J.
, and
Harper
J.S.
, J. Chem. Soc. , 1963 , 1276 .
21.
Hamed
A.A.
,
Badr
H.F.
, and
El-Ashry
E.H.
, Z. Naturforsch. , 2001 , 56B , 826 .
22.
Hamed
A.A.
,
Zeid
I.F.
,
El-Ganzory
H.H.
, and
Abdel Aal
M.T.
, Monatsh. Chem. , 2008 , in press.
23.
Gewald
K.
,
Schinke
E.
, and
Bottcher
H.
, Chem. Ber. , 1966 , 99 , 94 .
24.
Abdel-Fatah
A.M.
,
Aly
A.S.
,
Gad
F.A.
,
Hassan
N.A.
, and
El-Gazzar
A.B.A.
, Phosphorus, Sulfur, Silicon , 1991 , 60 , 223 .
25.
Shishoo
C.J.
,
Devani
M.B.
,
Ullas
G.V.
,
Ananthar
S.
, and
Bhadti
V.S.
, J. Heterocycl. Chem. , 1985 , 22 , 83
26.
Shishoo
C.J.
,
Devani
M.B.
,
Ullas
G.V.
,
Ananthar
S.
, and
Bhadti
V.S.
, J. Heterocycl. Chem. , 1981 , 18 , 43 .
27.
Shishoo
C.J.
,
Devani
M.B.
,
Ullas
G.V.
,
Ananthar
S.
, and
Bhadti
V.S.
, J. Heterocycl. Chem. , 1985 , 22 , 825 .
28.
Volkova
N.V.
,
Konyukhov
V.N.
,
Koksharova
T.G.
,
Dianova
L.G.
, and
Pushkareva
Z.V.
, Khim. Geterotsikl. Soedin. , 1979 , 262 .
29.
Khandker
M.H.B.
,
Rahman
M.
,
Abdur Rahim
K.H.
,
Hossain
M.I.
, and
Abu Nasser
M.
, Acta Pharm. , 2006 , 56 , 441 .