An efficient and rapid synthesis of 2,3-disubstituted-4(3H)quinazolinones by condensation of 2-aminobenzamide (substituted anthraniamides) with orthoesters in the presence of K-10 clay under solvent free conditions using microwave irradiation or classical heating is described.
For recent reviews see: LaszloP., Acc. Chem. Res., 1996, 19, 121; A. Cornelis and P. Laszlo, Synlett, 1994, 155; M, Balogh and P. Laszlo, Organic Chemistry Using Clays. Springer Verlag, New York, 1993.
2.
For recent reviews see: JinT.S., Chin. J. Org. Chem., 1996, 16, 385; B. Perio, M.J. Dozias, P. Jacquault and J. Hamelin, Tetrahedron Lett., 1997, 38, 7867; S. Jolivet-Fauchet, J. Hamelin, F. Texier-Boullet, L. Toupet and P. Jacquault, Tetrahedron, 1998, 54, 4561; K. Toshima, Y. Ushilci, G. Matsuo and S. Matsumura, Tetrahedron Lett., 1997, 38, 7375.
3.
AbramovitchR.A., Org. Prep. Proc. Int., 1991, 23, 683; D.M.P. Mingos and D.R. Baghurst, Chem. Soc. Rev., 1991, 20, 1-47; S. Caddick, Tetrahedron, 1995, 51, 10403; C.R. Strauss and R. W. Trainer, Aust. J. Chem., 1995, 48, 1665. For a review see: P. Lidström, J. Tierney, B. Wathey, and J. Westman, Tetrahedron, 2001, 57, 9225; A. Loupy, A. Petit. J. Hamelin, F. Texier- Boullet, P. Jacquault and D. Mathe, Synthesis, 1998, 1213.
4.
DeloudeL., and LaszloP., J. Org. Chem., 1996, 61, 6360; R.S. Varma and R. Dehiya, Synlett, 1997, 857; R.S. Varma and H.M. Meshram, Tetrahedron Lett., 1997, 38, 7973.
5.
OmarA.M. M. E, El-DinS. A. S., LaboutaI. M., and El-TambaryA. A., Alexandria J. Pharm. Sci., 1991, 5, 94 (Chem. Abstr., 1992, 116, 55402b).
6.
BaekD.J., ParkY. K., HeoH. I., LeeM. H., YangZ. Y., and ChoiM. H., Bioorg. Med. Chem. Lett., 1998, 8, 3287.
7.
NiementowskiV., J. Prakt. Chem., 1895, 51, 546.
8.
MakinoS., SuzukiN., NakanishiE., and TsujiT., Synlett., 2000, 1670.
9.
MayerJ.P., LewisG. S., CurtisM. J., and ZhangJ. W., Tetrahedron Lett., 1997, 38, 8445.
10.
YangR.Y., and KaplanA., Tetrahedron Lett., 2000, 41, 7005.
11.
DeetzM.J., MalerichJ. P., BeattyA. M., and SmithB. D., Tetrahedron Lett., 2001, 42, 1851.
12.
AlexanderF-R., BerecibarA., WrigglesworthR., and BessonT., Tetrahedron, 2003, 59, 1413; J.S. Yadav and B.V.S. Reddy, Tetrahedron Lett., 2002, 43, 1905; H. Hazarkhani and B. Karimi, Tetrahedron, 2003, 59, 4757.
13.
ClarkR.H., and WagnerE. C., J. Org. Chem., 1944, 9, 55.
14.
GrimmelH.W., GuentherA., and MorganJ. F., J. Am. Chem. Soc., 1946, 68, 542.
