RODRÍGUEZ ET AL.
9
80ꢀC for 1 minute. The reaction progress was monitored
by TLC in Hx:AcOEt. Upon completion, the reaction
mixture was extracted with CH2Cl2:H2O and thus con-
centrated. The organic phase was recrystallized in EtOH:
H2O to obtain the compounds 7a-v.
[11] Y. Qian, Y. Zhang, P. Zhong, K. Peng, Z. Xu, X. Chen, K. Lu,
G. Chen, X. Li, G. Liang, J. Cell. Mol. Med. 2016, 20, 1427.
[12] P. Budumuru, S. Golagani, B. Pushpanjali, Int. J. Pharm. Sci.
2019, 22, 1172.
[13] X. Yang, Q. Shang, C. Bo, L. Hu, Y. Zhou, ARKIVOC 2018, V, 184.
[14] B. M. Vieira, S. Thurow, M. da Costa, A. M. Casaril,
M. Domingues, R. F. Schumacher, G. Perin, D. Alves,
L. Savegnago, E. J. Lenardao, Asian J. Org. Chem. 2017, 6, 1635.
[15] R. N. Rao, M. M. Balamurali, B. Maiti, R. Thakuria,
K. Chanda, ACS Comb. 2018, 20, 164.
4.8 | Fluorescence and absorbance analysis
[16] P. Budumuru, S. Golagani, V. S. S. Kantamreddi, Asian
J. Pharm. Clin. Res. 2018, 11, 252.
[17] W. J. Dam, T. M. L. Tuong, D. W. Wang, D. Li, A. L. Zhang,
J. M. Gao, Bioorg. Med. Chem. Lett. 2018, 28, 2861.
[18] P. Lavanya, M. Suresh, Y. Kotaiah, N. Haarikrishna,
C. V. Rao, Asian J. Pharm. Clin. Res. 2011, 4, 69.
[19] (a) R. Goel, V. Luxami, K. Paul, Curr. Top. Med. Chem. 2016,
16, 3590. (b) T. Liu, X. Peng, Y. Ma, Y. Ji, D. Chen, M. Zheng,
D. Zhao, M. Cheng, M. Geng, J. Shen, J. Ai, B. Xiong, Acta
Pharmacol. Sin. 2016, 37, 698.
[20] (a) S. Xiao, Z. Liu, J. Zhao, M. Pei, G. Zhang, W. He, RSC Adv.
2016, 6, 27119-27125. (b) S. Srivastava, N. Thakur, A. Singh,
P. Shukla, V. Maikhuri, N. Garg, A. Prasad, R. Pandey, RSC
Adv. 2019, 9, 29856. (c) A. Shaily, A. Kumar, N. Ahmed,
Supramol. Chem. 2017, 29, 146.
The products obtained were dissolved in methanol,
THF, hexane, acetonitrile, and methylene chloride and
were observed under an UV-lamp at 254 and 365 nm.
2 × 10−5 M solutions of the 7e molecules were prepared
in MeOH, THF and CH2Cl2, and 4 × 10−7 M in CH3CN,
and subsequently the UV-absorbance spectra obtained
in a Jenway 7315 spectrophotometer. For the other
products, only MeOH and CH3CN were used at a
2 × 10−5 M concentration. The luminescence emission
was analyzed with a Spectrograph Spectra Acton Pro
3500i and a R955 photomultiplier tube from Hamama-
tsu. The system was PC controlled with Spectra Sense
software.
[21] (a) Z. Zhuand, M. Kung, A. Wilson, C. Lee, K. Plössl, C. Hou,
D. Holtzman, H. Kung, J. Med. Chem. 2003, 46, 237.
(b) C. Fookes, T. Pham, F. Mattner, I. Greguric, C. Loc'h,
X. Liu, P. Berghofer, R. Shepherd, M. Gregoire, A. Katsifis,
J. Med. Chem. 2008, 51, 3700.
[22] M. Pordel, H. Chegini, S. Ramezani, M. Daee, J. Mol. Struct.
2017, 1129, 105.
[23] A. J. Stasyuk, M. Banasiewicz, M. K. Cyranski, D. T. Gryko,
J. Organomet. Chem. 2012, 77, 5552.
ACKNOWLEDGMENTS
We acknowledge the financial support from the program
of Proyecto de Nuevo PTC 2018, Grant UACOAH-PTC-
456, and to Yolanda Ortega for her technical assistance.
ORCID
[24] S. Velázquez-Olvera, H. Salgado-Zamora, M. Velázquez-
Ponce, E. Campos-Aldrete, A. Reyes-Arellano, C. Pérez-
González, Chem. Cent. J. 2012, 6, 1.
[25] J. Catalán, E. Mena, F. Fabero, F. Amat-Guerri, J. Chem. Phys.
1992, 96, 2005.
[26] D. Firmansyah, A. Ciuciu, V. Hugues, M. Blanchard-Desce,
L. Flamigni, D. Gryko, Chem. Asian J. 2013, 8, 1279.
[27] T. Haruhiko, H. Takafumi, S. Shojiro, M. Toshiki, A. Koji,
Bull. Chem. Soc. Jpn. 1999, 72, 1327.
[28] D. M. Rackham, Appl. Spectrosc. 1979, 33, 561.
[29] S. Hu, D. Liu, C. Yan, M. Cai, Synth. Commun. 2018, 48, 2983.
REFERENCES
[1] B. M. Vieira, N. Padilha, N. M. Nascimento, G. Perin, D. Alves,
R. F. Schumacher, E. J. Lenardao, ARKIVOC 2019, ii, 6.
[2] S. A. Jadhav, M. G. Shiookar, O. S. Chavan, A. P. Sarkate,
D. B. Shinde, Synth. Commun. 2017, 47, 285.
[3] F. Tufail, S. Singh, M. Saquib, J. Tiwari, J. Singh, J. Singh,
Chem. Select. 2017, 2, 6082.
[4] C. He, J. Hao, H. Xu, Y. Mo, H. Liu, J. Han, A. Lei, Chem.
Commun. 2012, 48, 11073.
[5] S. Mishra, R. Ghosh, Synthesis 2011, 21, 3463.
[6] K. C. Chunavala, G. Joshi, E. Suresh, S. Adimurthy, Synthesis
2011, 4, 635.
SUPPORTING INFORMATION
Additional supporting information may be found online
in the Supporting Information section at the end of this
article.
[7] S. Santra, A. K. Bagdi, A. Majee, A. Hajra, Adv. Synth. Catal.
2013, 355, 1065.
[8] S. Ponnala, S. T. V. S. Kiran Kumar, B. A. Bhat, D. Prasad
Sahu, Synth. Commun. 2005, 35, 901.
[9] A. K. Bagdi, S. Santra, K. Monir, A. Hajira, Chem. Commun.
2015, 51, 1555.
[10] M. G. Rimoli, L. Avallone, P. de Caprariis, E. Luraschi,
E. Abignente, W. Filippelli, L. Berrino, F. Rossi, Eur. J. Med.
Chem. 1997, 32, 195.
How to cite this article: Rodríguez JC,
Maldonado RA, Ramírez-García G, Díaz
Cervantes E, de la Cruz FN. Microwave-assisted
synthesis and luminescent activity of imidazo[1,2-
a]pyridine derivatives. J Heterocyclic Chem. 2020;