NOVEL PHOTOSYNTHESIS AND CHARACTERIZATION OF 4-(5,7- DICHLORO-8aH-CHROMENE-2-YL)-N, N-DIMETHYLANILINE FROM ITS CHALCONE ISOMER
Keywords:
Chalcone, Chromene, FT-IR, NMR, LC/Q-TOF/MS, CHNO.
Abstract
In the present study, trans-3-(2,4-dichlorophenyl)-1-(4-(dimethylamino)phenyl)prop-2-en-1-one (trans
2,4-dimethyl amino chalcone) was synthesized by Claisen-Schmidt reaction in the presence of aqueous
alcoholic alkali solution by condensation of a substituted acetophenone with substituted benzaldehydes,
Then, The photosynthesis of 4-(5,7-dichloro-8aH-chromen-2-yl)-N,N-dimethylaniline (2,4-dimethylamino
chromene) was accomplished from the irradiation of the( trans 2,4-dimethyl amino chalcone) with xenon
light. The products were characterized by UV-Visible, FT-IR, 1HNMR, thin layer chromatography
Elemental analysis(CHNO) and liquid chromatography-quadrupole-time-of-flight mass spectrometry
(LC-Q-ToF-MS).
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References
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Reviews, 117(12), 7762–7810.
https://doi.org/10.1021/acs.chemrev.7b00020
Synthesis of some new chalcone derivatives
and evaluation of their Anticancer activity
Page. Int. J. Drug Dev. & Res., 6(1), 231–238.
Asiri, a. M., Karabacak, M., Sakthivel, S., Al-youbi,
A., Muthu, S., Hamed, S. a., … Alaganesan,
T. (2015). Synthesis, molecular structure,
spectral investigation on (E)-1-(4-
bromophenyl)-3-(4-
(dimethylamino)phenyl)prop-2-en-1-one.
Journal of Molecular Structure.
https://doi.org/10.1016/j.molstruc.2015.08.047
Bruice, P. Y. Organic Chemistry (4th Ed.). In:
(University of California, Santa Barbara)
published by Prentice Hall in 2004.
Costa, M., Dias, T. A., Brito, A., & Proença, F.
(2016). Biological importance of structurally
diversified chromenes. European Journal of
Medicinal Chemistry, 123, 487–507.
https://doi.org/10.1016/j.ejmech.2016.07.057
Dekić, M., Kolašinac, R., Radulović, N., Šmit, B.,
Amić, D., Molčanov, K., Marković, Z. (2017).
Synthesis and theoretical investigation of
some new 4-substituted flavylium salts. Food
Chemistry, 229(April), 688–694.
https://doi.org/10.1016/j.foodchem.2017.02.13
9
Gavara, R., Gago, S., Jordão, N., & Pina, F. (2014).
4’-carboxy-7-hydroxyflavylium. A multistate
system involving twelve species reversibly
interconverted by pH and light stimuli. The
Journal of Physical Chemistry. A, 118(26),
4723–4731. Retrieved from
http://www.ncbi.nlm.nih.gov/pubmed/248926
92
Kumar, D., Sharma, P., Singh, H., Nepali, K., Gupta,
G. K., Jain, S. K., & Ntie-Kang, F. (2017).
The value of pyrans as anticancer scaffolds in
medicinal chemistry. RSC Advances, 7(59),
36977–36999.
https://doi.org/10.1039/c7ra05441f
Mahadevan, D., Periandy, S., & Ramalingam, S.
(2011). Vibrational spectroscopy (FTIR and
FTRaman) investigation using ab initio (HF) and DFT (B3LYP) calculations on the
structure of 3-Bromo phenol. Spectrochimica
Acta - Part A: Molecular and Biomolecular
Spectroscopy, 78(2), 575–581.
https://doi.org/10.1016/j.saa.2010.11.025
Orlikova, B., Tasdemir, D., Golais, F., Dicato, M., &
Diederich, M. (2011). Dietary chalcones with
chemopreventive and chemotherapeutic
potential. Genes and Nutrition, 6(2), 125–147.
https://doi.org/10.1007/s12263-011-0210-5
Pavia, D.L., Lampman, G.M., Kriz, G.S. and Vyvyan,
J. A. (2014). Introduction to Spectroscopy 5th
Ed. Cengage Learning;.
Pratap, R., & Ram, V. J. (2014). Natural and
Synthetic Chromenes, Fused Chromenes, and
Versatility of Dihydrobenzo[ h ]chromenes in
Organic Synthesis. Chemical Reviews,
114(20), 10476–10526.
https://doi.org/10.1021/cr500075s
Rammohan, A., Reddy, J. S., Sravya, G., Rao, C. N.,
& Zyryanov, G. V. (2020). Chalcone
synthesis, properties and medicinal
applications: a review. Environmental
Chemistry Letters.
https://doi.org/10.1007/s10311-019-00959-w
RJ, K. (2011). An efficient fluorescent polymer
sensing material for detection of traces of
benzo [a] pyrene in environmental samples.
Environmental Chemistry Letters, 9, 389–395.
Robert M. Silverstein, F. X. W. (2005). Spectrometric
Identification of Organic Compounds 7th Ed.
Rosaleen J. Anderson, David J. Bendell, P. W. G.
(2004). Organic Spectroscopic Analysis.
Sudha, S., Sundaraganesan, N., Vanchinathan, K.,
Muthu, K., & Meenakshisundaram, S. (2012).
Spectroscopic (FTIR, FT-Raman, NMR and
UV) and molecular structure investigations of
1,5-diphenylpenta-1,4-dien-3-one: A
combined experimental and theoretical study.
Journal of Molecular Structure, 1030, 191–
203.
https://doi.org/10.1016/j.molstruc.2012.04.030
Tomasch, M., Schwed, J. S., Weizel, L., & Stark, H.
(2012). Novel chalcone-based fluorescent
human histamine H 3 receptor ligands as
pharmacological tools. Frontiers in SYSTEMS
NEUROSCIENCE, 6, 1–16.
https://doi.org/10.3389/fnsys.2012.00014
Tran, T.-D., Nguyen, T.-C.-V., Nguyen, N.-S.,
Nguyen, D.-M., Nguyen, T.-T.-H., Le, M.-T.,
& Thai, K.-M. (2016). Synthesis of Novel
Chalcones as Acetylcholinesterase Inhibitors.
Applied Sciences, 6(7), 198.
https://doi.org/10.3390/app6070198
Watanabe, H., Saji, H., & Ono, M. (2018). Novel
Fluorescence Probes based on the Chalcone
Scaffold for In vitro Staining of β-
Amyloid Plaques. Bioorganic & Medicinal
Chemistry Letters.
https://doi.org/10.1016/j.bmcl.2018.08.009
Yadav, N., Dixit, S. K., Bhattacharya, A., Mishra, L.
C., Sharma, M., Awasthi, S. K., & Bhasin, V.
K. (2012). Antimalarial Activity of Newly
Synthesized Chalcone Derivatives In Vitro.
Chemical Biology and Drug Design, 80(2),
340–347. https://doi.org/10.1111/j.1747-
0285.2012.01383.x
Zhou, B., Jiang, P., Lu, J., & Xing, C. (2016).
Characterization of the Fluorescence
Properties of 4-Dialkylaminochalcones and
Investigation of the Cytotoxic Mechanism of
Chalcones. Arch. Pharm. Chem. Life Sci, 349,
1–14. https://doi.org/10.1002/ardp.201500434
Zhuang, C., Zhang, W., Sheng, C., Zhang, W., Xing,
C., & Miao, Z. (2017). Chalcone: A Privileged
Structure in Medicinal Chemistry. Chemical
Reviews, 117(12), 7762–7810.
https://doi.org/10.1021/acs.chemrev.7b00020
Published
2020-12-11
How to Cite
CHALABI, N. A., & FADHIL, G. F. (2020). NOVEL PHOTOSYNTHESIS AND CHARACTERIZATION OF 4-(5,7- DICHLORO-8aH-CHROMENE-2-YL)-N, N-DIMETHYLANILINE FROM ITS CHALCONE ISOMER. Journal of Duhok University, 23(2), 135-149. https://doi.org/10.26682/sjuod.2020.23.2.15
Section
Pure and Engineering Sciences
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