Abstract
3-Aminoacrylonitrile derivatives (1d–g) coupled with aromatic and heteroaromatic diazonium salts yielding arylhydrazonals and pyrazolo[5,1-c]triazines. The enaminonitriles 1d–g condensed to form dienes 6a–c on reflux in acetic acid. The latter underwent Diels-Alder type addition to naphthoquinone. Aminopyrazolopyrimidines were obtained from reaction of 1d–g with heteroaromatic aminoazoles. Enaminonitrile 1d formed pyran 21 with benzylidene malononitrile, and dihydropyrimidine 22 with benzaldehyde and urea.
References
1.
Elassar A.A.
, and
El-khair A. A.
, Tetrahedron , 2003 , 59 , 8463 .
2.
Langer P.
, Angew. Chem. Int. Ed. , 2000 , 39 , 3049 .
3.
Davis K.M.
, and
Carpenter B. K.
, J. Org. Chem , 1996 , 61 , 4617 .
4.
Stanovnik B.
, J. Heterocycl. Chem. , 1999 , 36 , 1581 .
5.
Patai S.
, Ed, The Chemistry of Enamines , J. Wiley and Sons , New York , 1994 .
6.
Winter A.
, and
Risch N.
, Synlett , 2003 , 1 .
7.
Al-Zaydi K.M.
,
Hafiz E. A.
, and
Elnagdi M. H.
, J. Chem. Res. (S) , 2000 , 154 , 510 .
8.
Al-Omran F.
,
Khalik M. M. A.
,
El-Khair A. A.
, and
Elnagdi M. H.
, Synthesis , 1997 , 91 .
9.
Khalik M.M. A.
, and
Elnagdi M. H.
, Synthetic Commun. , 2002 , 32 , 159 .
10.
Al-Omran F.
,
Al-Awadi N.
,
El-Khair A. A.
, and
Elnagdi M. H.
, Org. Prep. Proc. Int. , 1997 , 29 , 285 .
11.
Al-Anezi A.
,
Al-Saleh B.
, and
Elnagdi M. H.
, J. Chem. Res. (S) , 1997 , 116 .
12.
El-Taweel F.M. A.
, and
Elnagdi M. H.
, J. Heterocyclic Chem. , 2001 , 38 , 981 .
13.
Al-Saleh B.
,
Al-Awadi N.
,
Abdel-khalik M. M.
, and
Elnagdi M. H.
, J. Chem. Res (S) , 2000 , 16 , 201 .
14.
Al-Mousawi S.
,
Abdel-khalik M. M.
,
John E.
, and
Elnagdi M. H.
, J. Heterocyclic Chem. , 2003 , 40 , 689 .
15.
Al-Saleh B.
,
Abdel-khalik M. M.
,
Salah O. A.
, and
Elnagdi M. H.
, Heteroatom Chem. , 2002 , 13 , 141 .
16.
Scotti F.
, and
Frazza E. J.
, J. Org. Chem. , 1964 , 29 , 1800 .
17.
Leonard E.C.
, Vinyl and Diene Monomers , p. 22 . Wiley-Interscience , New York 1970 .
18.
Rudolf G.
, and
Urich H.
, Angew. Chem. , 1981 , 93 , 297 .
19.
Wamhoff H.
,
Dzenis J.
, and
Hirota K.
, Adv. Heterocycl. Chem. , 1992 , 55 , 129 .
20.
Rene L.
;
Poncent J.
, and
Auzou G.
, Synthesis , 1986 , 419 .
21.
Al-Saleh B.
,
Al-Apasery M.
, and
Elnagdi M. H.
, J. Chem. Res. , 2004 , in press.
22.
Al-Saleh B.
,
Abdel-khalik M. M.
,
Eltoukhy A. M.
, and
Elnagdi M. H.
, J. Heterocyclic Chem. , 2002 , 39 , 1035 .
23.
Hassanien A.A.
,
Ghozlan S. A. S.
, and
Elnagdi M. H.
, J. Heterocyclic Chem. , 2003 , 40 , 225 .
24.
Elnagdi M. H.
,
Taha N. H.
,
Abdel-All F. A.
,
Abdel-Moteleb R. M.
, and
Mahmoud F. F.
, Collection Czech. Chem. Commun. , 1989 , 54 , 1982 .
25.
Elnagdi M.H.
,
Taha N. H
,
Abdell-All F. A.
,
Abdel-Moteleb R. M.
, and
Mahmoud F. F.
, Collection Czech. Chem. Commun. , 1989 , 54 , 1982
26.
Makino K.
,
Kim H. S.
, and
Kurasawa Y.
, J. Heterocyclic Chem. , 1998 , 35 , 489 and references therein.
27.
Behhbehani H.
,
Kalik M. A.
, and
Elnagdi M. H.
, Org. Prep. Proced. Int. , 1999 , 551 .
28.
Al-Zaydi K.M.
,
Borik R. M.
, and
Elnagdi M. H.
, Molecules , 2003 , 8 , 910 .
29.
Elnagdi M.H.
,
Elmoghayer M. R. H.
, and
Sadek K. U.
, Adv. Heterocyclic Chem. , 1990 , 48 , 223 .
30.
Ciller J.A.
,
Martin N.
,
Seoane C.
, and
Soto J. L.
, J. Chem. Soc., Perkin Trans. 1985 , 1 , 2581 .
