Abstract
In a multistep reaction, N-substituted-5′-amino-4′-cyano-1,3-dioxo-1,3-dihydro-spiro[indene-2,3′-pyrazole]-2′(1H) carbothioamides (63–71 %) and 4-substituted-3-thioxo-3H-indeno[1,2-e][1,2,4] triazin-9(4H)-ones (17–26 %) have been formed, from a series of 4-substituted thiosemicarbazides 1a–f with (1,3-dioxo-2,3-dihydro-1H-inden-2-ylidene)propanedinitrile 3 in aerated ethyl acetate. Rationales of these conversions involving the nucleophilic reactions and condensation are presented.
References
1.
Jung K.Y.
,
Kim S.K.
,
Gao Z.G.
,
Gross A.S.
,
Melman N.
,
Jacobson K.A.
, and
Kim Y.C.
, Bioorg. Med. Chem. , 2004 , 12 , 613 .
2.
Belicchi-Ferrari M.
,
Bisceglie F.
,
Casoli C.
,
Durot S.
,
Morgenslem-Badarau I.
,
Pelosi G.
,
Pilotti E.
,
Pinelli S.
, and
Tarasconi P.
, J. Med. Chem. , 2005 , 48 , 1671 .
3.
Pan K.
,
Scott M.K.
,
Lee D.H.S.
,
Fitzpatrick L.J.
,
Crooke J.J.
,
Riverno R.A.
,
Rosenthal D.I.
,
Vaidya A.H.
,
Zhao B.
, and
Reitz A.B.
, Bioorg. Med. Chem. , 2003 , 11 , 185 .
4.
Garcia C.C.
,
Brousse B.N.
,
Carlucci M.J.
,
Moglioni A.G.
,
Alho M.M.
,
Moltrasio G.Y.
,
D'Accorso N.B.
, and
Damonte E.B.
, Antiviral. Res. , 2000 , 57 , 61 .
5.
Kasuage N.C.
,
Sekino K.
,
Ishikawa M.
,
Honda A.
,
Yokoyama M.
,
Nakano S.
,
Shimada
,
koumo C.
, and
Nomiya K.
, J. Inorg. Biochem. , 2003 , 96 , 298 .
6.
Easmon J.
,
Purshinger G.
,
Heinisch G.
,
Roth T.
,
Fiebig H.H.
,
Holzer W.
,
Jäger W.
,
Jennny M.
, and
Hofmann J.
, J. Med. Chem. , 2001 , 44 , 2164 .
7.
Zelenin K.N.
,
Solod O.V.
,
Alekssav V.V.
,
Pekhk T.I.
,
Kuznetsova O.B.
,
Pekhk T.I.
,
Kuznetsova O.B.
,
Terent'ev P.B.
, and
Kalandarishvil G.
, Chem. Heterocycl. Comp. , 1990 , 26 , 1051 .
8.
El-Essawy F.A.
,
Khattab A.F.
, and
Abdel-Rahman A.A.-H.
, Monatsh. Chem. , 2007 , 138 , 77 .
9.
Öztür O.F.
, Trans. Met. Chem. , 2007 , 32 , 224 .
10.
Çapan G.
,
Ulusoy N.
,
Ergenç N.
, and
Kiraz M.
, Monatsh Chem. , 1999 , 130 , 1399 .
11.
Neidlein R.
, and
Ober W.-D.
, Monatsh Chem. , 1976 , 107 , 1252 .
12.
Shagun L.G.
,
Ermolyuk L.P.
,
Sara Pulova G.I.
, and
Dorofeev I.A.
, and
Voronkov M.G.
, Chem. Heterocycl. Comp. , 2005 , 41 , 946 .
13.
Fathalla W.
, and
Pazdera P.
, International Conference on Synthetic Organic Chemistry (ECSOC-11)1,3 November 2007 . http://www.usc.es/congresos/ecsoc/11/ECSOC11.htm.
14.
Dobosz M.
,
Pitucha M.
, and
Wujec M.
, Acta Pol. Pharm. , 1996 , 53 , 31
15.
Paul S.
,
Gupta V.
, and
Gupta R.
, Synth. Commun. , 2003 , 33 , 1917 .
16.
Tomita Y.
,
Kabashima S.
,
Okawara Y.
,
Yamasaki Y.
, and
Furukawa M.
, J. Heterocycl. Chem. , 1990 , 27 , 707 .
17.
Hassan A.A.
,
Mohamed N.K.
,
Shawky A.M.
, and
Döpp D.
, Arkivoc. , 2003 , ι , 118 .
18.
Hassan A.A.
,
Ibrahim Y.R.
,
Shawky A.M.
, and
Döpp D.
, J. Heterocycl. Chem. , 2006 , 43 , 849 .
19.
Aigner H.
,
Junek H.
, and
Sterk H.
, Monatsh. Chem. , 1970 , 101 , 1145 .
20.
Fischer-Colbrie H.
,
Aigner H.
, and
Juvek H.
, Monatsh. Chem. , 1975 , 106 , 743 .
21.
Junek H.
,
Aigner H.
, and
Fischer-Colbrve H.
, Monatsh. Chem. , 1972 , 103 , 639 .
22.
Rappoport Z.
, and
Ladkani D.
, J. Chem. Soc. (Perkin 2 )., 1973 , 1045 .
23.
Boila-Göckel A.
,
Fabian W.M.F.
, and
Junek H.
, Liebigs Ann. Chem. , 1996 , 397 .
24.
Hassan A.A.
, and
Shehatta H.S.
, J. Chem. Res. , 2007 , 629 .
25.
Kalinowski H.-O.
,
Berger S.
, and
Broun S.
(13C NMR Spektroskopie). , Thieme , Stuttgart , 1984 , p. 121
26.
Gewald K.
, and
Shnidler R.
, J. Prakt. Chem. , 1990 , 332 , 223 .
27.
Schulze K.
,
Richter C.
,
Ludwig R.
, and
Klatt K.
, Z. Chem. , 1988 , 28 , 288 .
28.
Hassan A.A.
,
Ibrahim Y.R.
, and
Shawky A.M.
, Z. Naturforsch. , 2008 , 63B , 998 .
29.
Stanovnik B.
, and
Tišler M.
, J. Org. Chem. , 1960 , 25 , 2234 .
30.
Eberhardt M.
,
Rabe J.
,
Anger I.
,
Schmidt J.
, and
Grunert H.
, East German Patent. , 1971 , 83 , 559 ; Appl. Wp Co7c 1970, 1149 , 657; Chem. Abstr. , 1973, 78 , 96674c.
31.
Pavanjpe M.G.
, and
Deshpand P.H.
, Indian J. Chem. , 1969 , 7 , 186 .
32.
Nikolaeva I.V.
,
Tsurkan A.A.
,
Levshin I.B.
,
Vyunov K.A.
, and
Ginak A.I.
, Zh. Parket. Khim. (Leningrad )., 1986 , 58 , 1189 ; Chem. Abstr., 1985, 103 , 177952h.
33.
Pohloudek-Fabini I.R.
, and
Goeckeritz D.
, Pharmazie. , 1962 , 17 , 515 .
34.
Vasil'eva E.B.
,
Sevenard D.V.
,
Khamutov O.G.
,
Kuznetsova O.A.
,
Karpenko N.S.
, and
Filyakova V.I.
, Russ. J. Org. Chem. (Translation of Zhurnal Organicheskoi, Khim )., 2004 , 40 , 874 .
35.
Chaterjee S.
, J. Chem. Soc. (B )., 1969 , 725 .