Abstract
A simple synthetic strategy is described for synthesis of hitherto unreported 3-arylazo derivatives of both [1,2,4]triazolo[4,3-a]benzimidazole and [1,2,4]triazolo[3,4-b]quinazolin-5-one 6 and 7, respectively. This strategy utilises reactions of 3-chloro-1,5-diarylformazans 1 with 2-mercaptobenzimidazole 2 and 2,3-dihydro-2-thioxoquina-zolin-4(1H)-one 4 or their 2-methylthio derivatives 3 and 5, respectively. A plausible reaction mechanism is suggested for the formation of the isolated products 6 and 7.
Keywords
References
1.
Shawali A.S.
, and
Mosselhi M. A. N.
, J. Heterocyclic Chem. , 2003 , 40 , 725 .
2.
(a)
Reynolds G.A.
, and
VanAllan J.
, J. Org. Chem. , 1959 , 24 , 1478 .
3.
Murdoch R.
,
Tully W. R.
, and
Westwood R.
, J. Heterocyclic Chem. , 1986 , 23 , 833 .
4.
(a)
Shawali A.S.
,
Abdelkhalek A. H.
, and
Sayed A. R.
, J. Chin. Chem. Soc. , 2001 , 48 , 693 .
5.
Shawali A.S.
,
Elghandour A. H.
, and
Sayed A. R.
, Synthetic Commun. , 2001 , 31 , 731 .
6.
Abdelhamid A.O.
,
Abbas I. M.
,
Abdallah M. A.
,
Fahmi A. A.
, and
Shawali A. S.
, J. Heterocyclic Chem. , 1985 , 22 , 813 .
7.
Gerard M.
,
Laurent V.
, and
Henri S.
, Eur. Pat. Appl. EP 1997 , 796850; Chem. Abstr. , 1997, 127 : 308426k.
8.
(a)
Ki-tack L.
,
Young-sub S.
,
Soon-yul U.
,
Woo-suk H.
, and
Bum-joon J.
, Repub. Korea KR , 1997 , 119 , 563 ; Chem. Abstr. , 2000, 133 , 224241g.
9.
Junji M.
, and
Tetsuo O.
, Jpn. Ko-kai Tokyo Koho JP 1998, 10 58, 843; Chem. Abstr. , 1998 , 128 , 218368j .
10.
Yukishi M.
, and
Miori I.
, Jpn. Ko-kai Tokyo Koho JP , 1998, 10 204, 307; Chem. Abstr. , 1998 , 129 , 204136r .
11.
Costa S.P. G.
,
Oliveira-Compos A. M. F.
,
Kirsch G.
, and
Griffths J.
, An. Quim. Int. Ed. , 1998 , 94 , 186 .
12.
(a)
Hallas G.
, and
Andrew T.
, Dyes Pigm. , 1996 , 32 , 135 .
13.
Choi J.H.
, Adv. Colour Sci. Technol., 1 , 1999 , 99 ; Chem. Abstr. , 1999, 131 , 46002d.
14.
Katsuta N.
, and
Ootake K.
, Jpn. Kokai Tokyo Koho JP , 1998, 10 237, 335; Chem. Abstr. , 1998 , 129 , 246517w .
15.
Seu G.
,
Mura L.
, and
Massacesi M.
, Am. Dyest. Rep. , 1997 , 86 , 57 ; Chem. Abstr. , 1997, 127 : 308411b.
16.
Tsien H.
,
Chu K.
, and
Chang H.
, U. S. US 1997 , 5 , 652 , 344; Chem. Abstr. , 1977, 127 , 150201w.
17.
Etzbach K.H.
,
Kraeh C.
,
Sens R.
, and
Wuerthner F.
, Ger. Offen. DE , 1997 , 19 , 611 , 351; Chem. Abstr. , 1997, 127 , 294577w.
18.
Hays B.G.
, U.S. pat. 1997 , 5, 669, 967; Chem. Abstr. , 1997, 127 , 279545r;
19.
(a)
Naik R.D.
,
Desai C. K.
, and
Desai K. R.
, Orient. J. Chem. , 2000 , 16 , 163 .
20.
Schaetzer J.
, Eur. Pat. Appl. EP 1997 , 776 , 948 ; Chem. Abstr. , 1997, 127 , 96564b.
21.
Schaetzer J.
, Ger. Offen. DE , 1997 , 19 , 646 , 429; Chem. Abstr. , 1997, 127 , 52209k.
22.
Schaetzer J.
, Ger. Offen. DE , 1997 , 19 , 646 , 430; Chem. Abstr. , 1997, 127 , 52210d.
23.
Desai T.R.
, and
Desai K. R.
, Asian J. Chem. , 1997 , 9 , 677 .
24.
(a)
Bradbury R.
,
Moscrop C.
,
Meyrick B. H.
, and
Holbrook M.
, Brit. UK Pat. Appl. GB 1999 , 2 , 335 , 924; Chem. Abstr. , 2000, 132 , 51147e.
25.
Tateishi K.
, Jpn. Kokai Tokyo Koho JP , 2001 , 181 , 537 ; Chem. Abstr. , 2001, 135 , 783474u.
26.
Tateishi K.
, Jpn. Kokai Tokyo Koho JP , 2001 , 181 , 538 ; Chem. Abstr. , 2001, 135 , 78348v.
27.
Seto N.
, and
Kamio T.
, Jpn. Kokai Tokyo Koho JP , 2000 , 355 , 660 ; Chem. Abstr. , 2001, 134 : 57938b.
28.
Vanallan J.A
, and
Deacon
, Org. Syn. , 1950 , 30 , 24 .
29.
Vanallan J.A
, J. Org. Chem. , 1956 , 21 , 24 .
30.
Rupe H.
, Ber. , 1897 , 30 , 1098 .
31.
Yun L.M.
,
Kh S.
,
Yangibaevis M.
,
Alekseeva V. Ya.
, and
Yunov V.
, Khim. Geterotsikl. Soedin. , 1986 , 9 , 1236 ; Chem. Abstr. , 1987, 106 , 176326g.
32.
Butler R.N.
,
Bhradaigh E. P. N.
,
McArdle P.
, and
Cunningham D.
, J. Chem. Res. , 1995 (S) 224 ; (M) 1401.
33.
(a)
Greenhill J.V.
,
Ismail M. J.
,
Bedford G. R.
,
Edwards P. N.
, and
Taylor P. J.
, J. Chem. Soc. Perkin Trans II , 1985 , 1265 .
34.
Bedford G.R.
, and
Taylor P. J.
, Mag. Res. Chem. , 1995 , 33 , 389 .
35.
Reiter J.
,
Pongo L.
, and
Dyortsak P.
, Tetrahedron , 1987 , 43 , 2597 .
36.
Hagiwara Y.
,
Kuriharaand M.
, and
Yoda N.
, Tetrahedron , 1969 , 25 , 783 .
