Green chemical principles based regioselective functionalization of 2,4,6-trichloropyrimidine-5-carbaldehyde: Application in the synthesis of new pyrimidines and pyrrolopyrimidine Scientific paper
Article Sidebar
Main Article Content
Abstract
The present work reports the synthesis of three new nitrogen-containing heteronuclear molecules (two pyrimidines and one pyrrolopyrimidine). Based on the 12 principles of green chemistry, chemical methodologies are planned and executed. Various phase transfer catalysts were examined in the crucial step to execute C–N bond formation (through the SnAr mechanism), TBAI was found to be a better option than those of TBAB and CTAB. The one-pot synthetic methodology was optimized involving Wittig olefination and bromination to achieve a key precursor for the synthesis of a new pyrrolopyrimidine.
Downloads
Metrics
Article Details
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution license 4.0 that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
References
P. K. Maji, Curr. Org. Chem 24 (2020) 1055 (https://doi.org/10.2174/1385272824999200507123843)
A. Mahapatra, T. Prasad, T. Sharma, Futur. J. Pharm. Sci. 7 (2021) 1 (https://doi.org/10.1186/s43094-021-00274-8)
H. K. Akula, H. Kokatla, G. Andrei, R. Snoeck, D. Schols, J. Balzarini, L. Yang, M. K. Lakshman, Org. Biomol. Chem. 15 (2017) 1130 (https://doi.org/10.1039/C6OB02334G)
S. Kumar, B. Narasimhan, Chem. Central J. 12 (2018) 38 (https://doi.org/10.1186/s13065-018-0406-5)
A. Frank,F. Meza-Arriagada, C. O. Salas, C. Espinosa-Bustos, H. Stark, Bioorg. Med. Chem. 27 (2019) 3194 (https://doi.org/10.1016/j.bmc.2019.05.042)
A. Ali, M. Khalid, M. F. U Rehman, S. Haq, A. Ali, M. N. Tahir, M. Ashfaq, F. Rasool, A. C. Braga, ACS Omega 5 (2020) 15115 (https://doi.org/10.1021/acsomega.0c00975)
A. Ali, M. Khalid, M. N. Tahir, M. Imran, M. Ashfaq, R. Hussain, M. A. Assiri, I. Khan, ACS Omega 6 (2021) 7047 (https://doi.org/10.1021/acsomega.0c06323)
A. Ali, A. Kuznetsov, M. Ashfaq, M. N. Tahir, M. Khalid, M. Imran, A. Irfan, J. Mol. Struct. 1243 (2021) 130789 (https://doi.org/10.1016/j.molstruc.2021.130789)
M. Khalid, A. Ali, S. Haq, M. N. Tahir, J. Iqbal, A. A. C. Braga, M. Ashfaq, S. U. H. Akhtar, J. Mol. Struct. 1224 (2021) 129308 (https://doi.org/10.1016/j.molstruc.2020.129308)
M. Ashfaq, A. Ali, A. Kuznetsov, M. N. Tahir, M. Khalid, J. Mol. Struct. 1228(2021) 129445 (https://doi.org/10.1016/j.molstruc.2020.129445)
S. Datta, S. Bhattacharya, Soft Matter. 11 (2015) 1945 (https://doi.org/10.1039/C4SM02792B)
P. K. Gu, S. Daunert, M. R. Nassiri, L. L. Wotring, J. C. Drach, L. B. Townsend, J. Med. Chem. 32(1989) 402 (https://doi.org/10.1021/jm00122a019)
D. S. Ramakrishna, Chem. Data Collect. 33 (2021) 100685 (https://doi.org/10.1016/j.cdc.2021.100685)
D. S. Ramakrishna, Chem. Data Collect. 32 (2021) 100667 (https://doi.org/10.1016/j.cdc.2021.100667).
D. S. Ramakrishna, A. Pradhan, ARKIVOC 2021 (2021) 1 (https://doi.org/10.24820/ark.5550190.p011.519)
G. Kumaraswamy, D. Ramakrishna, K. Santhakumar, Tetrahedron: Asymmetry 21 (2010) 544 (https://doi.org/10.1016/j.tetasy.2010.02.024)
G. Kumaraswamy, K. Sadaiah, D. S. Ramakrishna, N. Police, B. Sridhar, J. Bharatam, Chem. Commun. (2008) 5324 (https://doi.org/10.1039/B810770J)
G. Kumaraswamy, A. Pitchaiah, G. Ramakrishna, D. S. Ramakrishna, K. Sadaiah, Tetrahedron Lett. 47 (2006) 2013 (https://doi.org/10.1016/j.tetlet.2006.01.050)
H. P. Kokatla, M. K. Lakshman, Org. Lett. 20 (2010) 4478 (https://doi.org/10.1021/ol101655h)
R. Meesala, Y. K. Lee, A. S. Md. I. Abdullah, Md. N. Mordi, N. A. Rahman, Synlett 31 (2020) 2054 (DOI: 10.1055/s-0040-1706477)
R. Meesala, A. S. Md. Arshad, Md. N. Mordi, S. M. Mansor, Tetrahedron 72 (2016) 8537 (https://doi.org/10.1016/j.tet.2016.10.069)
J. M. Hatcher, J. Zhang, ‘H. G. Choi, G. Ito, D. R. Alessi, N. S. Gray, ACS Med. Chem. Lett. 6 (2015) 584 (https://doi.org/10.1021/acsmedchemlett.5b00064)
R. L. Beingessner, B. L. Deng, P. E. Fanwick, H. Fenniri, J. Org. Chem.73 (2008) 931 (https://doi.org/10.1021/jo7021422)
U. Karama, R. Mahfouz, Z. Al-Othman, I. Warad,A.Almansour, Synth. Comm. 43 (2013) 893(https://doi.org/10.1080/00397911.2011.614712)
Y. H. Jang, S. W. Youn, Org. Lett. 16 (2014) 3720 (https://doi.org/10.1021/ol5015398)
A. Udayasri, M. M. Chandrasekhar, M. V. N. Brahmeswararao, G. Varanasi, P. L. Praveen, D. S. Ramakrishna, TopCatal. (2022) (https://doi.org/10.1007/s11244-022-01602-9).