PPEG-mediated synthesis of 6-pyrazinyl-/fused pyrazinyl¬quinazolin-4(3H)-ones using Castro–Stephen coupling, oxidation and cyclocondensation reactions

Article Sidebar

PDF (2,235 kB) Supplementary Material (1.92 MB)
Published: May 21, 2020
DOI: https://doi.org/10.2298/JSC190517014P
Keywords:
KMnO4 Bisazaheterocycle 1 2-diamine 2-diketone

Main Article Content

Shankaraiah Pagilla
Department of Humanities and Sciences, Vardhaman College of Engineering, Shamshabad, Hyderabad-501218, Telangana
Angajala Kishore Kumar
Department of Humanities and Sciences, Vardhaman College of Engineering, Shamshabad, Hyderabad-501218, Telangana
Vianala Sunitha
Department of Chemistry, University College of Science, Osmania University, Saifabad, Hyderabad-500004, Telangana
Anagani Kanaka Durga Bhavani
Department of Chemistry, University College of Science, Osmania University, Hyderabad, 500007

Abstract

A PEG-mediated green synthesis of 6-pyrazinyl-/fused pyrazinyl­quinazolin-4(3H)-ones was developed starting from 6-iodo-3-methyl-2-phenyl­quinazolin-4(3H)-one by means of quinazolinone-based internal alkyne/1,2-diketone as intermediates using the Castro–Stephen coupling reaction/potas­sium permanganate mediated oxidation and cyclocondensation reactions.

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

Article Details

How to Cite
[1]
S. Pagilla, A. Kishore Kumar, V. Sunitha, and A. K. D. Bhavani, “PPEG-mediated synthesis of 6-pyrazinyl-/fused pyrazinyl¬quinazolin-4(3H)-ones using Castro–Stephen coupling, oxidation and cyclocondensation reactions”, J. Serb. Chem. Soc., vol. 85, no. 5, pp. 601–608, May 2020.
Issue
Vol. 85 No. 5 (2020)
Section
Organic Chemistry

Creative Commons лиценца
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.

Read more....

Crossref
Scopus
Google Scholar
Europe PMC

References

S. R. Pattan, V. Reddy, F. Manvi, B. Desai, A. Bhat, Indian J. Chem., B 45 (2006) 1778 (http://hdl.handle.net/123456789/6580)

A. S. El-Azab, Phosphorus Sulfur Silicon Relat. Elem. 182 (2007) 333 (http://dx.doi.org/10.1080/10426500600919207)

A. Yesilada, S. Koyunoglu, N. Saygili, E. Kupeli, E. Yesilada, E. Bedir, I. Khan, Arc. Der. Pharm. 337 (2004) 96 (http://dx.doi.org/10.1002/ardp. 200200752)

A. Patil, S. Ganguly, S. Surana, Asian J. Chem. 21 (2009) 1490 (http://dx.doi.org/10.1007/s12039-010-0052-5)

H. Kaur, A. Kumar, Int. J. Pharma Bio Sci. 1 (2010) 1 (http://citeseerx.ist.psu.edu/view-doc/download?doi=10.1.1.180.6399&rep=rep1&type=pdf)

I. J. Pachter, US 2866788 (1958)

P. G. Polishchuk, G. V. Samoylenko, T. M. Khristova, O. L. Krysko, T. A. Kabanova, V. M. Kabanov, A. Y. Kornylov, O. Klimchuk, T. Langer, S. A. Andronati, J. Med. Chem. 58 (2015) 7681 (http://dx.doi.org/10.1021/acs.jmedchem.5b00865)

S. L. Cao, Y. W. Guo, X. B. Wang, M. Zhang, Y. P. Feng, Y. Y. Jiang, Y. Wang, Q. Gao, J. Ren, Arch. Pharm. Chem. Life Sci. 342 (2009) 182 (http://dx.doi.org/10.1002/ardp.200800148)

P. Reddy, V. Mittapelli, V. Reddy, Rasayan J. Chem. 3 (2010) 635 (http://rasayanjournal.co.in/vol-3/issue-4/5.pdf)

P. Reddy, P. P. Reddy, T. Vasantha, Heterocycles 60 (2009)183 (https://ci.nii.ac.jp/naid/40005626824/)

A. M. Venkatesan, I. L. Jeremy, US 5281604 A (1994)

A. L. Banka, J. Botyanszki, M. Duan, M. R. Leivers, J. B. Shotwell, M. D. Tallant, S. H. Dickerson, V. W. Tai, R. B. Mcfadyen, A. M. Redman, J. Yu, X. LI, D. M. Garrido, J. G. Catalano, G. Adjabeng, WO 2012087938 (2012)

M. P. Trova, N. Zhang, WO 9823617 (1999)

C. C. Lee, L. Sun, M. Hoemann, D. Niu, D. Yan, R. C. Petter, H. Feng, WO 2007076086 (2007)

M. G. Stout, R. K. Robins, J. Org. Chem. 33 (1968) 1219 (http://dx.doi.org/10.1021/jo01267a061)

D. J. Brown, E. C. Taylor, J. A. Ellman, Quinoxalines, Suppl. 2, John Wiley & Sons, New York, 2004

T. Wei, J. Chen, X. Wang, Y. Zhang, L. Wang, Synth. Commun. 26 (1996) 1447 (http://dx.doi.org/10.1080/00397919608003507)

P. Li, H. Alper, J. Org. Chem.51 (1986) 4354 (http://dx.doi.org/10.1021/jo00373a005)

J. R. Blanton, Synth. Comnun. 27 (1997) 2093 (http://dx.doi.org/10.1080/00397919608003507)

P. Shankaraiah, S. Veeresham, A. K. D. Bhavan, Russ. J. Gen. Chem. 86 (2016) 368 (http://dx.doi.org/ 10.1134/S1070363216020286)

S. O. C. J. Rudolph, P. Coish, P. Wickens, G. Bondar, C. Y. Chuang, P. Ramsden, D. Lowe, D. Bierer, L. Chen, W. Fu, U. Khire, X. G. Liu, A. Mcclure, L. Wang, L. Yi, WO 2006012577A2 (2006)

J. J. Li, J. Nahra, A. R. Johnson, A. Bunker, P. OBrien, W.-S. Yue, D. F. Ortwine, C.-F. Man, V. Baragi, K. Kilgore, J. Med. Chem. 51 (2008) 835 (http://dx.doi.org/10.1021/jm701274v)

E. C. Lawson, W. A. Kinney, M. J. Costanzo, W. J. Hoekstra, J. A. Kauffman, D. K. Luci, R. Santulli, B. A. Tounge, S. C. Yabut, P. Andrade-Gordon, Lett. Drug Des. Discov. 1 (2004) 14 (http://dx.doi.org/10.2174/1570180043485644)

Y.-P. Zhu, Z. Fei, M.-C. Liu, F.-C. Jia, A.-X. Wu, Org. Lett. 15 (2012) 378 (http://dx.doi.org/10.1021/ol303331g)

M. S. Malamas, J. J. Erdei, W. F. Fobare, D. A. Quagliato, S. A. Antane, A. J. Robichaud, US 20070072925 (2008)

J. M. Hancock, A. P. Gifford, Y. Zhu, Y. Lou, S. A. Jenekhe, Chem. Mat. 18 (2006) 4924 (http://dx.doi.org/10.1021/cm0613760)

V. Vasin, Y. Y. Masterova, V. Razin, N. Somov, Can. J. Chem. 91 (2012) 465 (http://dx.doi.org/10.1139/cjc-2012-0159)

Z. R. Owczarczyk, W. A. Braunecker, A. Garcia, R. Larsen, A. M. Nardes, N. Kopidakis, D. S. Ginley, D. C. Olson, Macromolecules 46 (2013) 1350 (http://dx.doi.org/10.1021/ma301987p)

S.-J. Yoo, C.W. Jeon, J.-J. Ha, S.Y. Nam, S.C. Shin, J. Hwang, Y.-H. Kim, Macromol. Res. 21 (2013) 463 (http://dx.doi.org/10.1007/s13233-013-1108-4)

H. Yamashita, J. Abe, ‎J. Phys. Chem., A 115 (2011) 13332 (http://dx.doi.org/10.1021/jp204440s)

T. Q. Huang, W. Y. Qu, J. C. Ding, M. C. Liu, H. Y. Wu, J. X. Chen, J. Heterocycl. Chem. 50 (2013), 293 (http://doi.org/10.1002/jhet.1043).