A Simple and Convenient Synthesis of Isolated-Fused Heterocycles Based on: 2-Imino-N-phenyl-2H-chromene-3-carboxamide


Starting from 2-imino-N-phenyl-2H-chromene-3-carbox-amide, (1) a series of functionalized chromenes were achieved; such as, 2-ethoxy-2,3-dihydro-3-phenylchromeno[2,3-d]pyrimidin-4-one (2), and 2-hydrazinyl-2,3-dihydro-3-phenylchromeno-[2,3-d]pyrimidin-4-one (3). Furthermore, reactions of (3) with some of laboratory available compounds gave pyrazoles (4-9, 12, 13a, 13b), tetrazoles (11), 2-(2-benzylidenehydrazinyl)-3-phenyl-3H-chromeno[2,3-d]pyrimidin4(10H)-oneisoxazoles (14), 5-chloro-1-(4-oxo-3-phenyl-4,10-dihydro-3H-chromeno[2,3-d]pyrimidin-2-yl)-3-phenyl-2, 3-dihydro-1H-pyrazole-4-carbonitrile (17), pyrimidines (28a, b), pyridines (29a-29e, 30, 33a, 33b), benzo[b][1, 4]oxazepin-2- amines (32a, b), 3-chloro-4-(2-imino-2H-chromen-3-yl)-1-phenyl-4-(phenylamino) azetidin-2-one (34a-34e) and 2-(2- imino-2H-chromen-3-yl)-3-phenyl-2-(phenyl amino)thiazolidin-4-onee (35a-35e). The structures of these compounds were established by elemental analysis, IR, MS and NMR spectral analysis.


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I. El Azab and F. Abd El Latif, "A Simple and Convenient Synthesis of Isolated-Fused Heterocycles Based on: 2-Imino-N-phenyl-2H-chromene-3-carboxamide," Open Journal of Synthesis Theory and Applications, Vol. 1 No. 3, 2012, pp. 44-57. doi: 10.4236/ojsta.2012.13008.

Conflicts of Interest

The authors declare no conflicts of interest.


[1] A. M. El-Agrody M. S. Abd El-Latif, N. A. El-Hady, A. H. Fakery and A. H. Bedair, “Heteroaromatization with 4-Hydroxycoumarin Part II: Synthesis of Some New Pyrano[2, 3-d]pyrimidines,[1,2,4]triazolo[1,5-c]pyrimidines and Pyrimido[1,6-b]-[1,2,4]triazine Derivatives,” Molecules, Vol. 6, No. 6, 2001, pp. 519-527. doi:10.3390/60600519
[2] K. Mazaahir, S. Shilpi, M. R. K. Khalilur and S. T. Sharanjit, “Aqua Mediated Synthesis of Substituted 2-Amino4H-chromenes and in Vitro Study as Antibacterial Agents,” Bioorganic & Medicinal Chemistry Letters, Vol. 15, No. 19, 2005, pp. 4295-4298. doi:10.1016/j.bmcl.2005.06.041
[3] A. Luke, P. Soizic, S. Brigitte, M. Sylvie, K. Michel, T. C. Stewart, T. Fran?ois and L. J. Yves, European Journal of Medicinal Chemistry, 2009, pp. 1-9.
[4] B. Andrea, V. Nicole, T. Jakob, H. Sonja, B. Stefan and E. M. Christa, “Synthesis and Pharmacological Evaluation of Coumarin Derivatives as Cannabinoid Receptor Antagonists and Inverse Agonists,” Bioorganic & Medicinal Chemistry, Vol. 17, No. 7, 2009, pp. 2842-2851. doi:10.1016/j.bmc.2009.02.027
[5] P. Vassiliki, K. K. Ioannis, M. Panagiotis, P. Nicole and A. Ioanna, “Synthesis and Free Radical Scavenging Activity of Some New Spiropyranocoumarins,” Bioorganic & Medicinal Chemistry Letters, Vol. 18, No. 21, 2008, pp. 5781-5784. doi:10.1016/j.bmcl.2008.09.065
[6] N. Tadigoppula, K. Tanvir, N. Shweta, G. Neena and G. Suman, Bioorganic & Medicinal Chemistry, Vol. 13, No. 13, 2005, pp. 6543-6550.
[7] K. William, K. Shailaja, S. C. Jiang, H. Zhang, J. H. Zhao, S. J. Jia, L. F. Xu, C. Crogan-Grundya, R. Denis, N. Barriault, L. Vaillancourt, S. Charron, J. Dodd, G. Attardo, D. Labrecque, S. Lamothe, H. Gourdeau, B. Tseng, J. Drewea and S. X. Cai, “Discovery of 4-Aryl-4H-chromenes as a New Series of Apoptosis Inducers Using a Celland Caspase-Based High-Throughput Screening Assay. 2. Structure—Activity Relationships of the 7and 5-, 6-, 8-Positions,” Bioorganic & Medicinal Chemistry Letters, Vol. 15, No. 21, 2005, pp. 4745-4751. doi:10.1016/j.bmcl.2005.07.066
[8] G. Danielle, V. Samuel, L. M. Vijay, C. Frédéric, V. Guillaume, M. Florence, J. Philippe and G. René, “The Synthesis of New, Selected Analogues of the Pro-Apoptotic and Anticancer Molecule HA 14-1,” Tetrahedron Letters, Vol. 49, No. 20, 2008, pp. 3276-3278. doi:10.1016/j.tetlet.2008.03.070
[9] T. El-Sayed Ali, S. A.-A. Abdel-Aziz, H. M. El-Shaaer, F. I. Hanafy and A. Z. El-Fauomy, Turkish Journal of Chemistry, Vol. 32, 2008, pp. 365-374.
[10] M. K. Mostafa, H. F. A. Ashraf, A. E. Fathy and M. E. Ahmed, IL Farmaco, Vol. 57, 2002, pp. 715-722.
[11] A. G. Martinez and L. J. Marco, “Friedl?nder Reaction on 2-Amino-3-cyano-4H-pyrans: Synthesis of Derivatives of 4H-Pyran [2,3-b] Quinoline, New Tacrine Analogues,” Bioorganic & Medicinal Chemistry Letters, Vol. 7, No. 24, 1997, pp. 3165-3170. doi:10.1016/S0960-894X(97)10165-2
[12] C. P. Dell and C. W. Smith, European Patent No. EP537949, 1993.
[13] R. L. Dorta, A. Martin, E. Suárez and C. Betancor, “Endipitous Acid-Catalyzed Rearrangement of 13-Methoxy1,6,8-trioxadispiro[]pentadecane to 3-Chroman-5ylpropan-1-ol,” The Journal of Organic Chemistry, Vol. 62, No. 7, 1997, pp. 2273-2274. doi:10.1021/jo962065j
[14] Y. S. Vyacheslav, S. M. Vladimir and A. I. Roman, “Reactions of 3-(Polyfluoroacyl)chromones with Hydroxylamine. The First Synthesis of 3-Cyano-2-(polyfluoroalkyl)chromones,” Tetrahedron Letters, Vol. 47, No. 48, 2006, pp. 8543-8546. doi:10.1016/j.tetlet.2006.09.136
[15] D. Brian, Z. Liren, T. Junko, P. Joseph, H. Sarah, C. Brett, E. H. Christopher, W. Jenny, N. Christi, M. Ajay, S. David, W. Warren and S. G. Val, Bioorganic & Medicinal Chemistry Letters, Vol. 16, 2006, pp. 4237-4242.
[16] Y.-W. Guo, Y.-L. Shi, H.-B. Li and M. Shi, “Reactions of Salicyl N-Tosylimines or Salicylaldehydes with Diethyl Acetylenedicarboxylate for the Synthesis of Highly Functionalized Chromenes,” Tetrahedron, Vol. 62, No. 25, 2006, pp. 5875-5882. doi:10.1016/j.tet.2006.04.011
[17] Y. Seiji, M. Mikiko, M. Yohei, M. Masahiro and H. Yoshiro, Tetrahedron Letters, Vol. 45, 2004, pp. 6971-6973.
[18] E. H. E. Galal and H. H. E. Ahmed, “Activated Nitriles in Heterocyclic Synthesis. Novel Synthesis of 5-Imino-5H[1]benzopyrano[3,4-c]pyridine-4(3H)-thiones and Their Oxo Analogues,” Bulletin of the Chemical Society of Japan, Vol. 63, No. 4, 1990, pp. 1230-1232. doi:10.1246/bcsj.63.1230
[19] M. M. Rafat, Z. S. Hoda and H. E. Mohamed, Gazzetta Chimica Italiana, 1992, 122.
[20] M. K. Sergiy, E. B. Igor, M. S. Konstantyn, P. C. Valentyn and V. B. Yaroslav, “A New Pathway to 3-Hetaryl-2oxo-2H-chromenes: On the Proposed Mechanisms for the Reaction of 3-Carbamoyl-2-iminochromenes with Dinucleophiles,” Molecules, Vol. 5, No. 10, 2000, pp. 11461165. doi:10.3390/51001146
[21] S. Andrea, V. Daniel, L. André and F. ?ubomír, ARKIVOC, Vol. 6, 2001, pp. 122-128.
[22] T. Steinfuhrer, A. Hantschmann, M. Pietsch and M. Weissenfels, Liebigs Ann. Chem., Vol. 23, 1992.

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