European Journal of Chemistry

Reactivity of β-enamino ester of benzo[f]chromene: One pot synthesis of isolated and heterocycle-fused derivatives of benzo[f] chromene

Main Article Content

Eman Abd El-Rady
Islam Helmy El-Azab


The formation of isolated and fused benzo[f]chromene derivatives was achieved via reacting ethyl 3-amino-1-phenyl-1H-benzo[f]chromene-2-carboxylate (1) with some selected reagents under basic conditions. The new compound, ethyl 3-(dimethylaminomethyleneamino)-1-phenyl-1H-benzo[f]chromene-2-carboxylate  (2) was prepared from compound 1 and N,N-dimethyl formamide in presence of phosphorus oxychloride under mild conditions in excellent yield using Vilsmeier reaction. Also, 10-amino-12-phenyl-9-sulfanyl-12H-benzo[f] chromeno[2,3-d]pyrimidine-11(10H)-one (12), 10-aryl-14-phenyl-14H-benzo[f]chromeno [2,3-d][1,3,4]thiadiazolo[3,2-a]pyrimidine-13-one (15), ethyl 3-(4-oxo-2-thioxothiazolidin-3-yl)-1-phenyl-1H-benzo[f]chromene-2-carboxylate (18), ethyl 3-(4-phenyl-2-thioxothiazol-3(2H)-yl)-1-phenyl-1H-benzo[f]chromene-2-carboxylate (20), ethyl 3-acetamido-1-phenyl-1H-benzo[f]chromene-2-carboxylate (21), and 10-amino-9-methyl-12-phenyl-12H-benzo[f] chromeno[2,3-d]pyrimidine-11(10H)-one (23) were prepared. The structures of these compounds were established by elemental analysis, IR, MS and NMR spectral analy­sis.


icon graph This Abstract was viewed 2029 times | icon graph Article PDF downloaded 706 times

How to Cite
El-Rady, E. A.; El-Azab, I. H. Reactivity of β-Enamino Ester of benzo[f]chromene: One Pot Synthesis of Isolated and Heterocycle-Fused Derivatives of benzo[f] Chromene. Eur. J. Chem. 2012, 3, 81-86.

Article Details

Crossref - Scopus - Google - European PMC

[1]. Curini, M.; Cravotto, G.; Epifano, F.; Giannone, G. Curr. Med. Chem. 2006, 13, 199-222.

[2]. El Agrody, A. M.; Abd El Latif, M. S.; El Hady, N. A.; Fakery, A. H.; Badair, A. H. Molecules 2001, 6, 519-527.

[3]. Badair, A. H.; El Hady, N. A.; Abd El Latif, M. S.; Fakery, A. H.; El Agrody, A. M. Farmaco 2000, 55, 708-714.

[4]. El Agrody, A. M.; El Hakim, M. H.; Abd El Latif, M. S.; Fakery, A. H.; El Sayed, E. S. M.; El Ghareab, K. A. Acta Pharm. 2000, 50, 111-120.

[5]. Smith, W. P.; Sollis, L. S.; Howes, D. P.; Cherry, C. P.; Starkey, D. I.; Cobley, N. K. J. Med. Chem. 1998, 41, 787-797.

[6]. Taylor, R. N.; Cleasby, A.; Singh, O.; Sharzynski, T.; Wonacott, J. A.; Smith, W. P.; Sollis, L. S.; Howes, D. P.; Cherry, C. P.; Bethell, R.; Colman, P. J. Med. Chem. 1998, 41, 798-807.

[7]. Quagliato, D. A. US 5, 171, 857, Chem. Abstr., 118 (1993) 233887q.

[8]. Oganesyan, E. T.; Tuskaev, V. A.; Saraf, A. S.; Sarkisov, L. S. Russ, Ru 2, 039, 747, Chem. Abstr. 124 (1996) 316989z.

[9]. Koga, H.; Nabata, N.; H. PCT INT APP WO 92, 14 439, Chem. Abstr. 118 (1993) 233885n.

[10]. Martinez, A. G.; Marco, L. G.; Bioorg. Med. Chem. Lett. 1997, 7, 3165-3170.

[11]. Dell, C. P.; Smith. C. W. European Patent Appl. EP537949. Chem. Abstr. 119 (1993) 139102d.

[12]. Bianchi, G.; Tava, A. Agric, Biol. Chem. 1987, 51, 2001-2002.

[13]. Mohr, S. J.; Chirigos, M. A.; Fuhrman, F. S.; Pryor, J. W. Cancer Res. 1975, 35, 3750-3754.

[14]. Eiden, F.; Denk, F. Arch. Pharm. (Weinheim Ger.) 1991, 324, 353-354.

[15]. Kenny, R. S.; Mashelkar, U. C.; Rane, D. M.; Bezawada, D. K. Tetrahedron 2006, 62, 9280-9288.

[16]. Brun, P.; Guglielmetti, R.; Pepe, G.; Anguille, S. J. Photochem. Photobiol. A. Chem. 2003, 156, 77-82.

[17]. Eman, A. El Rady.; Magda, A. B. J. Heterocyclic Chem. 2008, 45, 1233-1236.

[18]. Eman, A. El Rady.; Mohamed, A. K. J. Chinese Chem. Soc. 2004, 51, 779-784.

[19]. Fawi, M. A. El Latif.; Eman, A. El Rady.; Mohamed, A. K. Phosphorus Sulfur 2002, 177, 2497-2505.

[20]. Eman, A. El Rady.; Magda, A. B. J. Heterocyclic Chem. 2006, 43, 243-247.

Supporting Agencies

Most read articles by the same author(s)

Dimensions - Altmetric - scite_ - PlumX

Downloads and views


Download data is not yet available.


Metrics Loading ...
License Terms

License Terms


Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License ( By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License ( are administered by Atlanta Publishing House LLC (European Journal of Chemistry).