Abstract
Treatment of 5,6-di(2-furyl)-3-thioxo-2,3-dihydropyridazine-4-carbonitrile with phosphonate carboanions stabilised with electron withdrawing group (CO2R, CN, SR’) led, under microwave irradiation and the effect of basic catalysis, to excellent yields of a variety of condensed sulfur, nitrogen and phosphorus-containing heterocycles as major products, along with fused thieno- and thiazole ring systems bearing a phosphonate moiety. On the other hand, fused thiazaphosphinine oxide and thiopyranone phosphonate were obtained in equal yields from the reaction of 5,6-di(2-furyl)-3-thioxo-2,3-dihydropyridazine-4-carbonitrile with diethyl vinylphosphonate. Screening results of antimicrobial potency for the products were discussed in terms of structure-activity relationships (SAR), and an attempt was made to define the structural features for lead compounds.
Keywords
References
1.
Majoural J.P.
, and
Bertrand G.
(eds), New aspects in phosphorus chemistry , Springer , Heidelberg, Germany , 2002 .
2.
Schmidpeter A.
, and
Karaghiosoff K.
, in Multiple bonds and low coordination in phosphorus chemistry ,
Regitz M.
, and
Scherer O. J.
, (eds), George Thieme Verlag , Stutgart , 1990 .
3.
Huang T.B.
, and
Zhang J. L.
, Phosphorus, Sulfur, Silicon , 1995 , 104 , 33 .
4.
Kar R.
, and
Ugi Z.
, Tetrahedron , 1990 , 46 , 3167 .
5.
Ota H.
,
Tanaka T.
,
Tono S.
, and
Fukuchi T.
, Jpn. Kokai Tokkyo Koho JP , 62, 234,090 (1986 ), Chem. Abstr. 1988, 109 , 22969.
6.
Wu S.Y.
, and
Hirashima A.
, Agric. Biol. Chem. , 1988 , 52 , 2911 .
7.
For recent account:
Abdou W.M.
,
Khidre M. D.
, and
Khidre R. E.
, J. Heteocycl. Chem. , 2008 , 45 , 1571 .
8.
Abdou W.M.
, and
Barghash R. F.
, Trends Heterocycl. , 2005 , 10 , 57 .
9.
Abdou W.M.
,
Ganoub N. A. F.
,
Fahmy A. F. M.
, and
Shaddy A. M.
, Phosphorus, Sulfur Silicon , 2004 , 180 , 2373 .
10.
Abdou W.M.
,
Salem M. A. I.
, and
Sediek A. A.
, Monatsh. Chem. , 2003 , 134 , 1373 .
11.
Abdou W.M.
,
Salem M. A. I.
, and
Sediek A. A.
, Bull. Chem. Soc. Jpn. , 2002 , 75 , 2481 .
12.
Abdou W.M.
, Phosphorus, Sulfur Silicon , 2002 , 177 , 325 .
13.
Abdou W.M.
,
Elkhoshnieh Y. O.
,
Salem M. A. I.
, and
Barghash R. F.
, Synlett 2002 , 1417 .
14.
Abdou W.M.
,
Sediek A. A.
, and
Khidre M. D.
, Monatsh. Chem. , 2008 , 139 , 617 .
15.
Abdou W.M.
,
Salem M. A. I.
, and
Barghash R. F.
, Arkivoc , 2007 , 15 , 45 .
16.
Abdou W.M.
,
Salem M. A. I.
, and
Barghash R. F.
, Synth. Commun. , 2003 , 33 , 1341 .
17.
Abdou W.M.
, and
Shaddy A. M.
, Lett. Org. Chem. , 2008 , 5 , 569 .
18.
Abdou W.M.
,
Khidre M. D.
, and
Khidre R. E.
, Eur. J. Med. Chem. , 2008 , in press.
19.
Abbady M.S.
, and
Radwan Sh. M.
, Phosphorus, Sulfur Silicon , 1994 , 86 , 203 .
20.
Silverstein R.M.
,
Webster F. X. W.
, and
Kiemle D. J.
, Spectrometric Identification of Organic Compounds , John, Wiley and Sons, Inc. 7th edn. 2005 .
21.
Otto Kalinowski H.
,
Berger St.
, and
Braun S.
, 13C NMR-Spektroscopie , Thieme Verlag , Stuttgart , 1984 .
22.
Kalyagin G.A.
,
Boldeskul I. E.
,
Egorov Yu. P.
, and
Balitskii Yu. V.
, Teor Eksp. Khim. , 1980 , 16 , 815 ; Chem. Abstr , 1981, 94 , 120688.
23.
Ciganek E.
, J. Org. Chem. , 1970 , 35 , 3631 .
24.
Vicente J.
,
Chicote M. T.
,
Fernandez-Baeza J.
, and
Lahoz F.
, J. Inorg. Chem. , 1991 , 30 , 3617 .
25.
Barnhardt R.G.
Jr.
, and
McEwen W. E.
, J. Am. Chem. Soc. , 1967 , 89 , 1009 .
26.
Yamakawa M.
,
Kubota T.
,
Terui Y.
,
Honma T.
, and
Tada Y.
, Bull. Chem. Soc. (Jpn) , 1978 , 51 , 3059 .
27.
Blade'-Font A.
,
McEwen W. E.
, and
Wanderwerf C. A.
, J. Am. Chem. Soc. , 1960 , 82 , 2646 .
28.
He L.N.
,
Cai R.
,
Chen Y.
, and
Zho J.
, Phosphorus, Sulfur and Silicon , 1997 , 130 , 65 .
29.
Arbuzov B.A.
,
Arshinova R. P.
, and
Sorokina T. D.
, Izv. Akad. NauK. SSSR, Ser Khim. , 1978 (9), 2010; Chem. Abstr. , 1979 , 90 , 22186 .
30.
Trippett S.
, J. Chem. Soc. , 1962 , 4733 .
31.
Boulos L.S.
, and
Abdel-Malek H. A.
, Phosphorus, Sulfur, Silicon , 2004 , 179 , 79 .
32.
Abdou W.M.
, and
Ganoub N. A. F.
, Phosphorus, Sulfur, Silicon , 1995 , 105 , 63 .
33.
Mercey J.M.
, and
Toube T. P.
, J. Chem. Res. (S) 1987 (3 ), 62 ; (M) 680.
34.
Boulos L.S.
, and
Arsanious M. H. N.
, Phosphorus, Sulfur, Silicon , 1994 , 89 , 185 .
35.
Yakout E.M. A.
,
Giurgius D. B.
, and
Boulos L. S.
, Phosphorus, Sulfur, Silicon , 1999 , 148 , 177 .
36.
Boulos L.S.
,
Arsanious M. H. N.
, and
Eldin N. K.
, Phosphorus, Sulfur, Silicon , 1997 , 122 , 49 .
37.
Abdou W.M.
, and
Khidre M. D.
, Phosphorus, Sulfur, Silicon , 2004 , 179 , 1307 .
38.
Caddick S.
, Tetrahedron , 1995 , 51 , 10403 .
39.
Varma R.S.
, Green Chem. , 1999 , 43 .
40.
Mojtahedi M.M.
,
Saidi M. R.
, and
Bolourtchian M.
, J. Chem. Res. (S) , 1999 , 710 .
41.
Kappe C.O.
, and
Stadler A.
, Microwaves in organic synthesis , 2nd ed.
Loupy A.
,
Kappe C. O.
(eds), Wiley-VCH , 2005 .
42.
Marvel G.
, Annual report on NMR spectroscopy ,
Mooney E.F.
(ed.), Academic Press , 1973 , Vol 58 .
43.
Zayed M.F.
,
El-Khoshnieh Y. O.
, and
Boulos L. S.
, Phosphorus, Sulfur, Silicon , 1991 , 62 , 251 .
44.
Abdou W.M.
,
Ganoub N. A. F.
, and
Mohamed A. A.
, Heterocycl. Commun. , 1997 , 3 , 57 .
45.
Schonberg A.
, and
Awad W. L.
, J. Chem. Soc. , 1945 , 197 .
46.
Schonberg A.
, and
Awad W. L.
, J. Chem. Soc. , 1947 , 651 .
47.
Abdou W.M.
,
Ganoub N. A.
,
Fahmy A. F. M.
, and
Shaddy A. M.
, Heteroatom Chem. , 2005 , 16 , 56 .
48.
Boyd M.R.
, Princ Pract Oncology , 1989 , 3 , 1 .
49.
Alley M.C.
,
Scudiero D. C.
,
Mönks A.
,
Flugsey M. L.
,
Czerwinski M. J.
,
Fine D. L.
,
Abbott B. J.
,
Mayo J. C.
,
Shoemaker R. H.
, and
Boyd M. R.
, Cancer Res. , 1988 , 48 , 589 .
50.
Zbiral E.
, Tetrahedron Lett. , 1970 , 5107 .
51.
Krespan C.G.
, J. Am. Chem. Soc. , 1961 , 83 , 33434 .
52.
Zbiral E.
, in Organophosphorus Reagents in Organic Synthesis ,
Cadogen J.I. G.
, Ed., 2nd edn. London , Academic Press 1979 , chap. 5, pp. 223 –268 .
53.
Abdou W.M.
, and
Hennawy I. T.
, Phosphorus, Sulfur, Silicon , 1994 , 89 , 105 .
54.
Abdou W.M.
, and
Ganoub N. A.
, Phosphorus, Sulfur, Silicon , 1995 , 105 , 63 .