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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 | Issue Date: March 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
DOI: 10.5155/eurjchem.5.1.133-137.923
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King Abdulaziz City for Science and Technology (KACST)
Citations
[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
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DOI: 10.1016/j.bioorg.2019.03.059
[2]. Ahmed M. Fouda, Mohammed A. Assiri, Ahmed Mora, Tarik E. Ali, Tarek H. Afifi, Ahmed M. El-Agrody
Microwave synthesis of novel halogenated β-enaminonitriles linked 9-bromo-1H-benzo[f]chromene moieties: Induces cell cycle arrest and apoptosis in human cancer cells via dual inhibition of topoisomerase I and II
Bioorganic Chemistry 93, 103289, 2019
DOI: 10.1016/j.bioorg.2019.103289
[3]. 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
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[4]. Ayman M. S. Youssef, Ahmed M. Fouda, Rasha M. Faty
Microwave assisted synthesis of some new thiazolopyrimidine and pyrimidothiazolopyrimidopyrimidine derivatives with potential antimicrobial activity
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DOI: 10.1186/s13065-018-0419-0
[5]. 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
[6]. 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
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DOI: 10.1016/j.tetlet.2015.02.081
[7]. Subrahmanya Ishwar Bhat
Catalyst-Free Cascade Synthesis of Densely Functionalized Chromenes in Water
Asian Journal of Chemistry 31(11), 2532, 2019
DOI: 10.14233/ajchem.2019.22191
[8]. 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
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DOI: 10.1016/j.jscs.2016.03.002
[9]. 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
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[10]. Tarek H. Afifi, Sayed M. Riyadh, Anwar A. Deawaly, Arshi Naqvi
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DOI: 10.1007/s00044-019-02387-5
[11]. 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
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DOI: 10.1007/s00044-013-0904-x
[12]. 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
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DOI: 10.1016/j.molstruc.2019.03.012
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