Cyclocondensation of 2-(1H-benzimidazol-2-yl)anilines 1a,b with carbon disulfide in the presence of potassium t-butoxide in boiling DMF afforded the corresponding benzimidazo[1,2-c]quinazoline-6(5H)-thiones 2a,b. Treatment of these compounds with hydrazine hydrate at reflux in ethanol gave the hydrazine derivatives 3a,b which were subsequently cyclised to the title compounds 4a–f on heating with orthoesters in ethanol.
(a) NarayanS.T.A., KumarV., and PujariH.K., Indian. J. Chem., Sect. B, 1986, 25, 267; (b) A. Chimirri, S. Grasso, G. Romeo and M. Zappala, Heterocycles, 1988, 27, 1975.
3.
(a) FenichelR.L., GregoryF.G., and AlburnH.E., Br. J. Cancer, 1976, 33, 329; (b) R.M. Scholtz, J.D. Papamatheakis, J. Luetzeler and M.A. Chirigos, Cancer Res., 1977, 37, 3338.
4.
(a) SchauerP., LikarM., StanovnikB., and TislerM., Biol. Vestn., 1972, 20, 65; (b) P.H.L. Wei and S.C. Bell, US Pat., 3 704 239 (Chem. Abstr., 1973, 78, 43482 m); (c) P.H.L. Wei and S.C. Bell, U.S. Pat. 3 775 426 (Chem. Abstr., 1974, 80, 70804u).
5.
AchesonR.M., and ElmoreN.F., Adv. Heterocycl. Chem., 1978, 23, 263.
6.
(a) HeraviM.M., and BakavoliM., J. Chem. Res. (S), 1995, 11, 480; (b) M.M. Heravi, G.H. Rajabzadeh, M. Rahimizadeh, M. Bakavoli and M. Ghassemzadeh, Phosphorus, Sulfur Silicon, 2001, 174, 129; (c) M.M. Heravi, N. Montazeri, M. Rahimizadeh, M. Bakavoli and M. Ghassemzadeh, J. Chem. Res. (S), 2000, 584; (d) M.M. Heravi, N. Montazeri, M. Rahimizadeh, M. Bakavoli and M. Ghassemzadeh, Monatsh. Chem, 2001, 132, 1225; (e) M. Rahimizadeh, Z. Tavallai and M. Bakavoli, Indian J. Chem, 2004, 43B, 679; (f) M.M. Heravi, A. Kivanloo, M. Rahimizadeh, M. Bakavoli and M. Ghassemzadeh, Tetrahedron Lett., 2004, 45, 5747; (g) M.M. Heravi, A. Kivanloo, M. Rahimizadeh, M. Bakavoli, B. Neumuller and M. Ghassemzadeh, Tetrahedron Lett., 2005, 46, 1607; (h) M. Bakavoli, G. Bagherzadeh and M. Rahimizadeh, Mendeleev Commun, 2005, 4, 145; (i) M.M. Heravi, M. Bakherad, M. Rahimizadeh, M. Bakavoli and M. Ghassemzadeh, Heterocycl. Commun., 2004, 10, 335; (j) M. Bakavoli, M. Nikpour and M. Rahimizadeh, Phosphorus, Sulfur Silicon, 2005, 180, 2265; (k) M. Bakavoli, B. Reihani, M. Rahimizadeh and M. Nikpour, Phosphorus, Sulfur Silicon, 2006, 181, 99.
7.
(a) BakavoliM., DavoodniaA., RahimizadehM., HeraviM.M., and GhassemzadehM., J. Chem. Res. (S), 2002, 178; (b) M. Bakavoli, A. Davoodnia, M. Rahimizadeh and M.M. Heravi, Mendeleev Commun., 2006, 16, 29; (c) A. Davoodnia, M. Bakavoli, A. Vahedinia, M. Rahimizadeh and M. Roshani, Heterocycles, 2006, 68, 801.
8.
(a) ChaurasiaM.R., and SharmaA.K., J. Indian. Chem. Soc., 1983, 60, 1071; (b) R.H. Bahekar and A.R. Rao, Indian J. Pharm. Sci, 2000, 62, 41; (c) V.B. Rao and C.V. Ratnam, Indian J. Chem. Sect. B, 1977, 15B, 1100; (d) P. Molina, M. Alajarin and A. Vidal, Tetrahedron Lett., 1988, 29, 3849.
9.
ZaikiaL.L., and JoulliéM.M., J. Heterocycl. Chem., 1966, 3, 289; L.L. Zaikia, Diss. Abstr., 1965, 25, 6976 (Univ. of Pennsylvania, USA.) (Chem. Abstr. 1965, 63, 13261e).
10.
MolinaP., AlajarinM., and VidalA., Tetrahedron, 1989, 45, 4263.