A convenient method for the synthesis of ethyl 6-substituted 6,7,8,9-tetrahydro-2-thia-3,5,6,9-tetraazabenz[cd]azu-lene-1-carboxylates – representing a new heterosystem – from the corresponding ethyl 4,5-diaminothieno[2,3-d]pyrimidine-6-carboxylates, by a two-step protocol is described.
References
1.
TaylorE.C., PatelH. H., SabithaG., and ChaudhariR., Heterocycles, 1996, 43, 349; A.A. Geies, J. Chem. Res., 1998, (S) 290; (M) 1248; M. Robba, D. Laduree, C. Fossey, J. Renault and F. Jourdan, J. Pharm. Belg., 1995, 50, 121; Z.A. Hozien, F.M. Atta, K.M. Hassan, A.A. Abdel-Wahab and S.A. Ahamed, Synth. Commun., 1996, 26, 3733; A. Rosowsky, A.T. Papoulis and S.F. Queener, J. Med. Chem., 1997, 40, 3694; A.M.K. El-Dean, Monatsh. Chem., 1998, 129, 523; J. Clark and G. Hitiris, J. Chem. Soc., Perkin Trans. 1, 1984, 2005; R.K. Russell, J.B. Press, R.A. Rampulla, J.J. McNally, R. Falotico, J.A. Keiser, D.A. Bright and A. Tobia, J. Med. Chem., 1988, 31, 1786; C.J. Shishoo, M.B. Devani, V.G. Bhadti, K.S. Jain, I.S. Rathod, R.K. Goyal, T.P. Gandhi, R.B. Patel and G.R. Nail, Arzneim.-Forsch., 1990, 40, 567; R.J. Ife, T.H. Brown, P. Blurton, D.J. Keeling, C.A. Leach, M.L. Meeson, M.E. Parsons and C.J. Theobald, J. Med. Chem., 1995, 38, 2763
2.
R.K. Russel and R.A. Rampulla, USP 4939137/1990 (Chem. Abstr., 1990, 113, 212 008); A.N. Grinev and N.V. Kaplina, Khim. Geterotsikl. Soedin., 1985, 925; RusselR.K., RampullaR. A., NieveltC. E., and KlaubertD. H., J. Heterocycl. Chem., 1990, 27, 1761.
3.
(a) TumkeviciusS., and PupeikyteR., J. Chem. Res., 1995, (S) 286
BellarosaD., AntonelliG., BambacioniF., GiannottiD., VitiG., NanniciniR., GiachettiA., DianzaniF., WitvrouwM., PauwelsR., DesmyterJ., and De ClercqE., Antiviral Res., 1996, 30, 109; M. Guetschow, K. Droessler, and S. Leistner, Arch. Pharm. (Weinheim, Ger.), 1995, 328, 231; M.J. Fray, D.J. Bull, K. Cooper, J. Parry and M.H. Stefaniak, J. Med. Chem., 1995, 38, 3524; R. Pauwels, K. Andries, J. Desmyter, D. Schols,; M.J. Kukla, H.J. Breslin, A. Raeymaeckers, J. Van Gelder, R. Woestenborgs, J. Haaykants, K. Schellekens, M.A.C. Janssen, E. De Clercq and P.A.J. Jannsen, Nature, 1990, 343, 470.
6.
SantilliA.A., KimD. H., and WanserS. V., J. Heterocycl. Chem., 1971, 8, 445.
7.
TumkeviciusS., and KaminskasA., Chemija (Vilnius), 1999, 140.