Abstract
Polyfunctional 4-(3-cyanopyridin-2-ylthio)acetoacetates were used in the synthesis of 4-hydroxy-1H -thieno[2,3-b :4,5-b ]dipyridin-2-ones. The latter were used in reactions with arylidenemalononitriles or in three-component reactions with aldehydes and malononitrile to give 2-amino-4-aryl-3-cyano-5-oxo-5,6-dihydro-4H -pyrano[2,3-d ]pyrido[3′,2′:4,5]thieno[3,2-b ]pyridines. Utilizing 4-(3-cyanopyridin-2-ylthio)acetoacetates and arylidenemalononitriles or aldehydes and malononitrile, we developed a method for the synthesis of substituted 3-alkoxycarbonyl-6-amino-4-aryl-2-(3-cyanopyridin-2-ylthiomethyl)-4H -pyrans. Reactions of substituted 4-(3-cyanopyridin-2-ylthio)acetoacetates with hydrazine hydrate yielded substituted 3-hydroxypyrazoles, which were further used for the preparation of 6-amino-4-aryl-5-cyano-3-(pyrid-2-ylthiomethylene)-2,4-dihydropyrano[2,3-c ]pyrazoles. Analogously, ethyl 4-(3-cyano-1,4-dihydropyridin-2-ylthio)acetoacetates were used for the synthesis of substituted 2-amino-4H -pyrans.
Key words
2-amino-4H -pyrans - thienopyridines - 4-(3-cyanopyridin-2-ylthio)acetoacetates - pyranopyridines - multi-component reactions
References
1
Rodinovskaya LA.
Shestopalov AM.
Russ. Chem. Bull. Int. Ed.
2000,
49:
348
2
The Merck Index
13th ed.:
Merck and Co.;
Whitehouse Station NJ / USA:
2001.
p.1818
3
Litvinov VP.
Rodinovskaya LA.
Sharanin YA.
Shestopalov AM.
Senning A.
Sulfur Rep.
1992,
13:
1
4 Urbahns K, Heine H.-G, Junge B, Mauler F, Wittka R, and De Vry J.-M.-V. inventors; Eur. Pat. 758647.
; Chem. Abstr . 1997 , 126 , 225216v
5 Tanaka KT, Makino SK, Oshio IT, Shimotori TT, Aikawa YT, Inaba TN, Yoshida CT, Takano SM, and Taniguchi YT. inventors; Eur. Pat. 695547.
; Chem. Abstr . 1996 , 124 , 23835c
6 Ambler SJ, Heath WF, Singh JP, Smith CW, and Stramm LE. inventors; Eur. Pat. 619314.
; Chem. Abstr . 1995 , 122 , 31327d
7
Joshi KC.
Jain R.
Arora S.
J. Indian Chem. Soc.
1988,
65:
277
8
Panda D.
Singh JP.
Wilson L.
J. Biol. Chem.
1997,
272:
7681
9
Rodinovskaya LA.
Shestopalov AM.
Gromova AV.
Russ. Chem. Bull. Int. Ed.
2003,
52:
2185
10
Sharanin YA.
Goncharenko MP.
Litvinov VP.
Russ. Chem. Rev. (Engl. Transl.)
1998,
67:
393
11
Elagamey AGA.
Sowellim SZA.
El-Taweel FMAA.
Elnagdi MH.
Collect. Czech. Chem. Commun.
1988,
53:
1534
12
Sharanina LG.
Promonenkov VK.
Marshtupa VP.
Pashchenko AV.
Puzanova VV.
Sharanin YA.
Klyuev NA.
Gusev LF.
Gnatusina AP.
Chem. Heterocycl. Compd.
1982,
18:
607
13
Shestopalov AM.
Emeliyanova YM.
Shestopalov AA.
Rodinovskaya LA.
Niazimbetova ZI.
Evans DH.
Org. Lett.
2002,
4:
423
14
Shestopalov AM.
Yakubov AP.
Tsyganov VV.
Emel’yanova YM.
Nesterov VN.
Chem. Heterocycl. Compd.
2002,
38:
1180
15
Sharanin YA.
Sukharevskaya LY.
Shelyakin VV.
Russ. J. Org. Chem.
1998,
34:
552
16
Piao MZ.
Imafuku K.
Tetrahedron Lett.
1997,
38:
5301
17
Rodinovskaya LA.
Gromova AV.
Shestopalov AM.
Nesterov VN.
Russ. Chem. Bull. Int. Ed.
2003,
52:
2207
18 The X-ray diffraction study was performed by Doct. Sci. (Chem.) V. S. Sergienko at the N. S. Kurnakov Institute of General and Inorganic Chemistry (Moscow).
19
Sheldrick GM.
SHELXS97. Program for the Solution of Crystal Structures
University of Göttingen;
Germany:
1997.
20
Sheldrick GM.
SHELXL97. Program for the Refinement of Crystal Structures
University of Göttingen;
Germany:
1997.