European Journal of Chemistry 2014, 5(1), 133-137. doi:10.5155/eurjchem.5.1.133-137.923

Microwave assisted synthesis of 2-amino-6-methoxy-4H-benzo[h]chromene derivatives


Ahmed Mohamed El-Agrody (1,*) , Al-Anood Mohamed Al-Dies (2) , Ahmed Mahmoud Fouda (3)

(1) Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, 11884, Egypt
(2) Chemistry Department, Faculty of Science, King Khalid University, Abha, 61413, Saudi Arabia
(3) Chemistry Department, Faculty of Science, King Khalid University, Abha, 61413, Saudi Arabia
(*) Corresponding Author

Received: 10 Sep 2013, Accepted: 13 Oct 2013, Published: 31 Mar 2014

Abstract


A convenient and efficient method using microwave assisted synthesis of 4H-benzo[h]chromenes (7 and 8), by the reaction of 4-methoxy-1-naphthol (1) with a mixture of aromatic aldehydes (2) and malononitrile (3) or ethyl cyanoacetate (5) and also, by the reaction of 4-methoxy-1-naphthol (1) with α-cyanocinnamonitriles (4) or ethyl α-cyanocinnamates (6) in ethanolic piperidine solution was examined. Structures of the newly synthesized compounds were established on the basis of spectral data, IR, 1H NMR, 13C NMR, 13C NMR-DEPT and MS data.


Keywords


Benzochromenes; Pyran derivatives; Microwave synthesis; 4-Methoxy-1-naphthol; α-Cyanocinnamonitriles; Ethyl α-cyanocinnamates

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DOI: 10.5155/eurjchem.5.1.133-137.923

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[1]. Fawzia F. Alblewi, Rawda M. Okasha, Zainab M. Hritani, Hany M. Mohamed, Mohammed A.A. El-Nassag, Ahmed H. Halawa, Ahmed Mora, Ahmed M. Fouda, Mohammed A. Assiri, Al-Anood M. Al-Dies, Tarek H. Afifi, Ahmed M. El-Agrody
Antiproliferative effect, cell cycle arrest and apoptosis generation of novel synthesized anticancer heterocyclic derivatives based 4H-benzo[h]chromene
Bioorganic Chemistry  87, 560, 2019
DOI: 10.1016/j.bioorg.2019.03.059
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[2]. Fawzia Alblewi, Rawda Okasha, Areej Eskandrani, Tarek Afifi, Hany Mohamed, Ahmed Halawa, Ahmed Fouda, Al-Anood Al-Dies, Ahmed Mora, Ahmed El-Agrody
Design and Synthesis of Novel Heterocyclic-Based 4H-benzo[h]chromene Moieties: Targeting Antitumor Caspase 3/7 Activities and Cell Cycle Analysis
Molecules  24(6), 1060, 2019
DOI: 10.3390/molecules24061060
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[3]. Ayman M. S. Youssef, Ahmed M. Fouda, Rasha M. Faty
Microwave assisted synthesis of some new thiazolopyrimidine and pyrimidothiazolopyrimidopyrimidine derivatives with potential antimicrobial activity
Chemistry Central Journal  12(1), , 2018
DOI: 10.1186/s13065-018-0419-0
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[4]. Shivaputra A Patil, Siddappa A Patil, Renukadevi Patil
Microwave-assisted synthesis of chromenes: biological and chemical importance
Future Medicinal Chemistry  7(7), 893, 2015
DOI: 10.4155/fmc.15.38
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[5]. Ivan N. Bardasov, Anastasiya U. Alekseeva, Denis L. Mihailov, Oleg V. Ershov, Dmitry A. Grishanov
Double heteroannulation reactions of 1-naphthol with alkyl- and arylmethylidene derivatives of malononitrile dimer
Tetrahedron Letters  56(14), 1830, 2015
DOI: 10.1016/j.tetlet.2015.02.081
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[6]. Ahmed M. El-Agrody, Ahmed H. Halawa, Ahmed M. Fouda, Al-Anood M. Al-Dies
The anti-proliferative activity of novel 4H-benzo[h]chromenes, 7H-benzo[h]-chromeno[2,3-d]pyrimidines and the structure–activity relationships of the 2-, 3-positions and fused rings at the 2, 3-positions
Journal of Saudi Chemical Society  21(1), 82, 2017
DOI: 10.1016/j.jscs.2016.03.002
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[7]. Rawda Okasha, Fawzia Albalawi, Tarek Afifi, Ahmed Fouda, Al-Anood Al-Dies, Ahmed El-Agrody
Structural Characterization and Antimicrobial Activities of 7H-Benzo[h]chromeno[2,3-d]pyrimidine and 14H-Benzo[h]chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidine Derivatives
Molecules  21(11), 1450, 2016
DOI: 10.3390/molecules21111450
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[8]. Tarek H. Afifi, Sayed M. Riyadh, Anwar A. Deawaly, Arshi Naqvi
Novel chromenes and benzochromenes bearing arylazo moiety: molecular docking, in-silico admet, in-vitro antimicrobial and anticancer screening
Medicinal Chemistry Research  28(9), 1471, 2019
DOI: 10.1007/s00044-019-02387-5
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[9]. Ahmed M. El-Agrody, Ahmed M. Fouda, Al-Anood M. Al-Dies
Studies on the synthesis, in vitro antitumor activity of 4H-benzo[h]chromene, 7H-benzo[h]chromene[2,3-d]pyrimidine derivatives and structure–activity relationships of the 2-,3- and 2,3-positions
Medicinal Chemistry Research  23(6), 3187, 2014
DOI: 10.1007/s00044-013-0904-x
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[10]. Hany E.A. Ahmed, Mohammed A.A. El-Nassag, Ahmed H. Hassan, Hany M. Mohamed, Ahmed H. Halawa, Rawda M. Okasha, Saleh Ihmaid, Shimaa Mohamed Abd El-Gilil, Essam S.A.E.H. Khattab, Ahmed M. Fouda, Ahmed M. El-Agrody, Ateyatallah Aljuhani, Tarek H. Afifi
Developing lipophilic aromatic halogenated fused systems with specific ring orientations, leading to potent anticancer analogs and targeting the c-Src Kinase enzyme
Journal of Molecular Structure  1186, 212, 2019
DOI: 10.1016/j.molstruc.2019.03.012
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How to cite


El-Agrody, A.; Al-Dies, A.; Fouda, A. Eur. J. Chem. 2014, 5(1), 133-137. doi:10.5155/eurjchem.5.1.133-137.923
El-Agrody, A.; Al-Dies, A.; Fouda, A. Microwave assisted synthesis of 2-amino-6-methoxy-4H-benzo[h]chromene derivatives. Eur. J. Chem. 2014, 5(1), 133-137. doi:10.5155/eurjchem.5.1.133-137.923
El-Agrody, A., Al-Dies, A., & Fouda, A. (2014). Microwave assisted synthesis of 2-amino-6-methoxy-4H-benzo[h]chromene derivatives. European Journal of Chemistry, 5(1), 133-137. doi:10.5155/eurjchem.5.1.133-137.923
El-Agrody, Ahmed, Al-Anood Mohamed Al-Dies, & Ahmed Mahmoud Fouda. "Microwave assisted synthesis of 2-amino-6-methoxy-4H-benzo[h]chromene derivatives." European Journal of Chemistry [Online], 5.1 (2014): 133-137. Web. 16 Sep. 2019
El-Agrody, Ahmed, Al-Dies, Al-Anood, AND Fouda, Ahmed. "Microwave assisted synthesis of 2-amino-6-methoxy-4H-benzo[h]chromene derivatives" European Journal of Chemistry [Online], Volume 5 Number 1 (31 March 2014)

DOI Link: https://doi.org/10.5155/eurjchem.5.1.133-137.923

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