Abstract
The reactions of 6-methoxybenzo[b]furan-3(2H)-one with 2-aryl-1,1-dicyanoethylenes and malononitrile or with aromatic aldehyde and two moles of malononitrile afford 2-amino-4-aryl-1,3-dicyano-7-methoxydibenzo[b,d]furans. The reactions of benzo[b]thiophen-3(2H)-one with 2-aryl-1,1-dicyanoethylenes or with aromatic aldehyde and one mole of malononitrile produce 2-amino-4-aryl-3-cyano-4H-benzothieno[3,2-b]pyrans.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
V. S. Velezheva, D. E. Gedz´, D. V. Gusev, A. S. Peregudov, B. V. Lekshin, and Z. S. Klemenkova, Tez. dokl. 1-i Mezhdunar. konf. "Khimiya i biologicheskaya aktivnost´ azotistykh geterotsiklov i alkanov" [Abstrs. 1st Intern. Conf. "Chemistry and Biological Activity of Nitrogen-containing Geterocycles and Alkaloid] (Moscow, October 9-12, 2000), Iridium Press, Moscow, 2001, 1, 247 (in Russian).
V. S. Velezheva, K. V. Nevskii, and N. N. Suvorov, Khim. Geterotsikl. Soedin., 1985, 230 [Chem. Heterocycl. Compd., 1985, 21, 235 (Engl. Transl.)].
O. Naumov and A. Shestopalov, Abstrs. 7th Blue Danube Symp. on Heterocyclic Chemistry (Eger, Hungary, 1998), Eger, 1998, 124.
C. J. Adams and L. Main, Tetrahedron, 1991, 47, 4979.
Yu. A. Sharanin, V. K. Promonenkov, and V. P. Litvinov, Malononitril, Itogi nauki i tekhniki, Ser. Organicheskaya khimiya [Malononitrile, Advances in Science and Technology, Ser. Organic Chemistry], VINITI, Moscow, 1991, 20, Part 1, 239 pp. (in Russian).
M. Dewar and R. Doherti, Teoriya vozmushchenii molekulyarnykh orbitalei v organicheskoi khimii [Perturbation Theory of Molecular Orbitals in Organic Chemistry], Mir, Moscow, 1977, 273 pp. (Russ. Transl.).
Yu. A. Sharanin, V. K. Promonenkov, and L. G. Sharanina, Zh. Org. Khim., 1982, 18, 625 [J. Org. Chem. USSR, 1982, 18, 544 (Engl. Transl.)].
Yu. A. Sharanin, L. N. Shcherbina, L. G. Sharanina, and V. V. Puzanova, Zh. Org. Khim., 1983, 19, 164 [J. Org. Chem. USSR, 1983, 19, 150 (Engl. Transl.)].
M. S. Chauhan and I. W. J. Still, Can. J. Chem., 1975, 53, 2880.
A. Blom and J. Tambor, Ber., 1905, 38, 3590.
C. Hansch and H. G. Lindwell, J. Org. Chem., 1945, 10, 383.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Shestopalov, A.M., Naumov, O.A. Reaction of 6-methoxybenzo[b]furan-3(2H)-one and benzo[b]thiophen-3(2H)-one with 2-aryl-1,1-dicyanoethylenes as a convenient synthetic route to substituted 2-amino-4-aryl-1,3-dicyano-7-methoxydibenzo[b,d]furans and 2-amino-4-aryl-3-cyano-4H-benzothieno[3,2-b]pyrans. Russian Chemical Bulletin 52, 961–968 (2003). https://doi.org/10.1023/A:1024468813689
Issue Date:
DOI: https://doi.org/10.1023/A:1024468813689
- 6-methoxybenzo[b]furan-3(2H)-one
- 6-methoxy-2-[(4-aryl)methylidene]-1-benzofuran-3(2H)-one
- 2-amino-4-aryl-1,3-dicyano-7-methoxydibenzo[b,d]furan
- benzo[b]thiophen-3(2H)-one
- 2-[(4-aryl)methylidene]-1-benzothiophen-3(2H)-one
- 2-amino-4-aryl-3-cyano-4H-benzothieno[3,2-b]pyran
- three-component condensation
- stability