Abstract
2-Cyano-2-carboximidic acid alkyl ester-oxiranes react with hydrazides and carbazates to give epoxy acylamidrazones. Some of the last ones are precursors of tetrasubstituted push-pull alkenes, which in turn can be efficiently converted into 3,5-diaminopyrazoles. Using ortho -phenylenediamine as nucleophile directly affords 3,4-dihydro-2, 2’-biquinoxalines.
Key words
oxiranes - epoxyacylamidrazones - diaminopyrazoles - biquinoxalines
References
1
Hurtaud D.
Baudy-Floc"h M.
Le Grel P.
Tetrahedron Lett.
1999,
40:
5001
2
Robert A.
Baudy-Floc"h M.
Le Grel P.
Foucaud A.
Trends in Organic Chemistry
1995,
5:
37
3
Le Grel P.
Baudy-Floc"h M.
Robert A.
Synthesis
1987,
306
4a
Aubry A.
Mangeot JP.
Vidal J.
Collet A.
Zerkout S.
Marraud M.
Int. J. Pept. Prot. Res.
1994,
43:
305
4b
Yang D.
Qu J.
Li B.
Ng FF.
Wang XCC.
Cheung KK.
Wang DP.
Wu YD.
J. Am. Chem. Soc.
1999,
121:
589
4c Cheguillaume, A.; Salaün, A.; Sinbandhit , S.; Potel, M.; Gall, P.; Baudy-Floc’h, M.; Le Grel, P. J. Org. Chem. 2001 , in press.
5a
Neilson G.
Roger R.
Heatlie JWM.
Newlands LR.
Chem. Rev.
1970,
70:
151
5b
Reimlinger H.
Lingier WRF.
Vandewalle JJM.
Chem. Ber.
1971,
104:
639
5c
Mc Killop A.
Henderson A.
Ray PS.
Avendano C.
Malinero EG.
Tetrahedron Lett.
1982,
23:
3357
5d
Francis JE.
Gorczyca LA.
Mazzenga GC.
Meckler H.
Tetrahedron Lett.
1987,
28:
5133
5e
Cocco MT.
Congiu C.
Onnis V.
Maccioni A.
J. Heterocycl. Chem.
1991,
28:
797
6a
Vaquero JJ.
Fuentes L.
Del Castillo JC.
Pérez MI.
Garcia JL.
Soto JL.
Synthesis
1987,
33
6b
Echevarria A.
Elguero J.
Yranzo GI.
Diez-Barra E.
de la Hoz A.
Moreno A.
Garcia-Martin MA.
J. Chem. Soc., Perkin Trans. 1
1993,
2229
6c
Elnagdi MH.
El-Ghamry I.
Kandeel E.
Rahman AHA.
Al-Naggar AA.
Amer S.
Riad M.
Gaz. Chim. Ital.
1997,
127:
791
7
Yammaghuchi Y.
Okamoto Y.
Harada K.
J. Heterocycl. Chem.
1999,
36:
841
8
Taylor EC.
Maryanoff CA.
Skotnicki JS.
J. Org. Chem.
1980,
45:
2512
9a
Epifani E.
Florio S.
Ingrosso G.
Sgarra R.
Stasi F.
Tetrahedron
1987,
43:
2769
9b
Sheinkman AK.
Lopatinskaya KY.
Terent"ev PB.
Chem. Heterocycl. Compd.
1985,
21:
805
9c
Baranowska I.
Monatsh. Chem.
1987,
118:
659
10
Bouchet P.
Elguero J.
Jacquier R.
Pereillo JM.
Bull. Soc. Chim. Fr.
1972,
6:
2264
11 Crystallographic data (without structure factors) for the structure reported in this paper have been deposited at the Cambridge Crystallographic Data Center as supplementary publication no. CCDC - 135239. Copies of the data can be obtained free of charge on application to CCDC, 12 Union road, Cambridge CB2 1EZ, UK [Fax: (inter.) +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk].