European Journal of Chemistry 2012, 3(1), 81-86 | doi: https://doi.org/10.5155/eurjchem.3.1.81-86.507 | Get rights and content






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


Eman Abd El-Rady (1,*) , Islam Helmy El-Azab (2)

(1) South Valley University, Faculty of Science, Chemistry Department, Aswan 81528, Egypt
(2) South Valley University, Faculty of Science, Chemistry Department, Aswan 81528, Egypt
(*) Corresponding Author

Received: 22 Aug 2011 | Accepted: 18 Oct 2011 | Published: 31 Mar 2012 | Issue Date: March 2012

Abstract


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.

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Keywords


Spectral analysis; Elemental analysis; Vilsmeier reaction; Phosphorus oxychloride; Benzo[f]chromeno[2,3-d]pyrimidine; Benzo[f]chromeno[2,3-d][1,3,4]thiadiazolo[3,2-a]pyrimidine

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DOI: 10.5155/eurjchem.3.1.81-86.507

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[2]. Islam El Azab, Mohamed Youssef, Mahmoud Amin
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[3]. Islam H. El Azab, Nadia A. A. Elkanzi, Adil A. Gobouri
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[5]. Ashraf Hassan Fekry Abd El-Wahab, Hany Mostafa Mohamed, Ahmed Mohamed El-Agrody, Ahmed Hammam Bedair
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[8]. Islam H. El Azab, Khaled M. Khaled
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[11]. Islam H. El Azab, Mohamed R. E. Aly, Adil A. Gobouri
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How to cite


El-Rady, E.; El-Azab, I. Eur. J. Chem. 2012, 3(1), 81-86. doi:10.5155/eurjchem.3.1.81-86.507
El-Rady, E.; El-Azab, I. 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(1), 81-86. doi:10.5155/eurjchem.3.1.81-86.507
El-Rady, E., & El-Azab, I. (2012). Reactivity of β-enamino ester of benzo[f]chromene: One pot synthesis of isolated and heterocycle-fused derivatives of benzo[f] chromene. European Journal of Chemistry, 3(1), 81-86. doi:10.5155/eurjchem.3.1.81-86.507
El-Rady, Eman, & Islam Helmy El-Azab. "Reactivity of β-enamino ester of benzo[f]chromene: One pot synthesis of isolated and heterocycle-fused derivatives of benzo[f] chromene." European Journal of Chemistry [Online], 3.1 (2012): 81-86. Web. 6 Jul. 2020
El-Rady, Eman, AND El-Azab, Islam. "Reactivity of β-enamino ester of benzo[f]chromene: One pot synthesis of isolated and heterocycle-fused derivatives of benzo[f] chromene" European Journal of Chemistry [Online], Volume 3 Number 1 (31 March 2012)

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DOI Link: https://doi.org/10.5155/eurjchem.3.1.81-86.507

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