Mass Spectrometry of Substituted Ethyl-4-anilinopyrazolo[3,4-b]pyridine-5-carboxylates

Samia Khakwani; Samina Aslam; Mehrzadi Noureen Shahi; Alice M. Rolim Bernardino; Misbahul Ain Khan

doi:10.14233/ajchem.2016.19477

Issue

Vol. 28 No. 4 (2016): Vol 28 Issue 4

Issue Published : December 30, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Mass Spectrometry of Substituted Ethyl-4-anilinopyrazolo[3,4-b]pyridine-5-carboxylates

https://doi.org/10.14233/ajchem.2016.19477

Samia Khakwani

Department of Chemistry, The Women University Multan, Multan, Pakistan

Samina Aslam

Department of Chemistry, The Women University Multan, Multan, Pakistan; Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, Pakistan

Mehrzadi Noureen Shahi

Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, Pakistan

Alice M. Rolim Bernardino

Departamento de Quimica Organica, Instituto de Quimica, Universidade Federal Fluminense, Niteroi, RJ, 24020-150, Brazil

Misbahul Ain Khan

Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, Pakistan

Corresponding Author(s) : Samina Aslam

saminaaslam2009@gmail.com

Asian Journal of Chemistry, Vol. 28 No. 4 (2016): Vol 28 Issue 4
Article Published : December 30, 2015

Abstract

The mass spectra of a number of ethyl 4-anilinopyrazolo [3,4-b]pyridine-5-carboxylates are presented. The fragmentation is initiated by the elimination of ethanol molecule followed by the elimination of CO (m/z 28) and HCN molecules. In another alternative route an HCl may be removed followed by the CO loss (m/z 28). Further loss of one or more molecules of HCN (m/z 27) brings to shorter fragments till a fragment corresponding to a phenyl C₆H₅ (m/z 77) radical cation is reached.

Keywords

Fragmentations Pyrazolopyrimidines Pyrazolopyridines Cyclizations

Khakwani, S., Aslam, S., Shahi, M. N., Rolim Bernardino, A. M., & Khan, M. A. (2015). Mass Spectrometry of Substituted Ethyl-4-anilinopyrazolo[3,4-b]pyridine-5-carboxylates. Asian Journal of Chemistry, 28(4), 789–792. https://doi.org/10.14233/ajchem.2016.19477

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References

C.R. Hardy, Adv. Heterocycl. Chem., 36, 343 (1984); doi:10.1016/S0065-2725(08)60117-8.
M. Chauhan and R. Kumar, Bioorg. Med. Chem., 21, 5657 (2013); doi:10.1016/j.bmc.2013.07.027.
H.W. Hamilton, D.F. Ortwine, D.F. Worth and J.A. Bristol, J. Med. Chem., 30, 91 (1987); doi:10.1021/jm00384a016.
S.A. Poulsen and R.J. Quinn, J. Med. Chem., 39, 4156 (1996); doi:10.1021/jm960052s.
F.A. Harden, R.J. Quinn and P.J. Scammells, J. Med. Chem., 34, 2892 (1991); doi:10.1021/jm00113a031.
B.M. Lynch, M.A. Khan, H.C. Teo and F. Pedrotti, Can. J. Chem., 66, 420 (1988); doi:10.1139/v88-074.
A.M. Salaheldin, A.M.F. Oliveira-Campos and L.M. Rodrigues, Tetrahedron Lett., 48, 8819 (2007); doi:10.1016/j.tetlet.2007.10.079.
A.M.R. Bernardino, V.F. Ferreira, G.A.T. Fontoura, I.C.P.P. Frugulhetti, M.Y. Lee, G.A. Romeiro, M.C.B. Souza and P.M. Sá, J. Braz. Chem. Soc., 7, 273 (1996); doi:10.5935/0103-5053.19960055.
V.D. Someshwar, S.R. Bhupendra, G.G. Maruti, B.G. Vishwas and B.D. Avinash, J. Chem. Pharm. Res., 6, 540 (2014).
M. Hassan, V. Yadav, B. Kumar and B. Ahmad, Int. J. Adv. Pharm. Sci., 1, 329 (2013).
S.C. Santosh, G.M. Gajanan, S.Y. Omprakash, S.K. Santosh and S.D. Bhaskar, Int. J. Chem. Tech. Res., 3, 938 (2011).
A. Chaubey and S.N. Pandeya, Asian J. Pharm. Clinical Res., 4, 5 (2011).
F.C. Teixeira, M.C. Lucas, M. João, M. Curto, M. Neves, M.T. Duarte, V. Andréc and A.P.S. Teixeira, J. Braz. Chem. Soc., 24, 1295 (2013); doi:10.5935/0103-5053.20130164.
M.A. Khan and A. Mustafa, Pharmazie, 2, 813 (1986).
T. Maqbool, M.A. Khan, M.N. Khan, M.C. Elliott, M.A. Munawar, M. Nasrullah, A.W. Bhatti and A. Nazeer, Asian J. Chem., 25, 7715 (2013); doi:10.14233/ajchem.2013.14573A.
T. Maqbool, A. Nazeer, M.N. Khan, M.C. Elliott, M.A. Khan, M. Ashraf, M. Nasrullah, S. Arshad and M.A. Munawar, Asian J. Chem., 26, 2870 (2014); doi:10.14233/ajchem.2014.15918.
N. Perveen, S. Aslam, T. Maqbool, A.M.R. Bernadino and M.A. Munawar, Afinidad, 71, 566 (2014).
A.R. de Azevedo, I.C.P.P. Frugulhetti, M.A. Khan, S. Khakwani and A.M.R. Bernardino, Heterocycl. Commun., 8, 47 (2002); doi:10.1515/HC.2002.8.1.47.
Q.N. Porter and J. Baldas, in eds.: A. Weissbeger and E.C. Taylor, Mass Spectrometry of Heterocyclic Compounds, Wiley-Interscience, New York (1971).
F.W. McLafferty, Decomposition and Rearrangements of Organic Ions, in Mass Spectrometry of Organic Ions, Academic Press, New York (1963).
R.G. Gould and W.A. Jacobs, J. Am. Chem. Soc., 61, 2890 (1939); doi:10.1021/ja01265a088.
A. Zaman, M.A. Khan, M.A. Munawar, M. Athar, M. Pervaiz, A. Pervaiz and A. Mahmood, Asian J. Chem., 27, 2823 (2015); doi:10.14233/ajchem.2015.18094.

References

C.R. Hardy, Adv. Heterocycl. Chem., 36, 343 (1984); doi:10.1016/S0065-2725(08)60117-8.

M. Chauhan and R. Kumar, Bioorg. Med. Chem., 21, 5657 (2013); doi:10.1016/j.bmc.2013.07.027.

H.W. Hamilton, D.F. Ortwine, D.F. Worth and J.A. Bristol, J. Med. Chem., 30, 91 (1987); doi:10.1021/jm00384a016.

S.A. Poulsen and R.J. Quinn, J. Med. Chem., 39, 4156 (1996); doi:10.1021/jm960052s.

F.A. Harden, R.J. Quinn and P.J. Scammells, J. Med. Chem., 34, 2892 (1991); doi:10.1021/jm00113a031.

B.M. Lynch, M.A. Khan, H.C. Teo and F. Pedrotti, Can. J. Chem., 66, 420 (1988); doi:10.1139/v88-074.

A.M. Salaheldin, A.M.F. Oliveira-Campos and L.M. Rodrigues, Tetrahedron Lett., 48, 8819 (2007); doi:10.1016/j.tetlet.2007.10.079.

A.M.R. Bernardino, V.F. Ferreira, G.A.T. Fontoura, I.C.P.P. Frugulhetti, M.Y. Lee, G.A. Romeiro, M.C.B. Souza and P.M. Sá, J. Braz. Chem. Soc., 7, 273 (1996); doi:10.5935/0103-5053.19960055.

V.D. Someshwar, S.R. Bhupendra, G.G. Maruti, B.G. Vishwas and B.D. Avinash, J. Chem. Pharm. Res., 6, 540 (2014).

M. Hassan, V. Yadav, B. Kumar and B. Ahmad, Int. J. Adv. Pharm. Sci., 1, 329 (2013).

S.C. Santosh, G.M. Gajanan, S.Y. Omprakash, S.K. Santosh and S.D. Bhaskar, Int. J. Chem. Tech. Res., 3, 938 (2011).

A. Chaubey and S.N. Pandeya, Asian J. Pharm. Clinical Res., 4, 5 (2011).

F.C. Teixeira, M.C. Lucas, M. João, M. Curto, M. Neves, M.T. Duarte, V. Andréc and A.P.S. Teixeira, J. Braz. Chem. Soc., 24, 1295 (2013); doi:10.5935/0103-5053.20130164.

M.A. Khan and A. Mustafa, Pharmazie, 2, 813 (1986).

T. Maqbool, M.A. Khan, M.N. Khan, M.C. Elliott, M.A. Munawar, M. Nasrullah, A.W. Bhatti and A. Nazeer, Asian J. Chem., 25, 7715 (2013); doi:10.14233/ajchem.2013.14573A.

T. Maqbool, A. Nazeer, M.N. Khan, M.C. Elliott, M.A. Khan, M. Ashraf, M. Nasrullah, S. Arshad and M.A. Munawar, Asian J. Chem., 26, 2870 (2014); doi:10.14233/ajchem.2014.15918.

N. Perveen, S. Aslam, T. Maqbool, A.M.R. Bernadino and M.A. Munawar, Afinidad, 71, 566 (2014).

A.R. de Azevedo, I.C.P.P. Frugulhetti, M.A. Khan, S. Khakwani and A.M.R. Bernardino, Heterocycl. Commun., 8, 47 (2002); doi:10.1515/HC.2002.8.1.47.

Q.N. Porter and J. Baldas, in eds.: A. Weissbeger and E.C. Taylor, Mass Spectrometry of Heterocyclic Compounds, Wiley-Interscience, New York (1971).

F.W. McLafferty, Decomposition and Rearrangements of Organic Ions, in Mass Spectrometry of Organic Ions, Academic Press, New York (1963).

R.G. Gould and W.A. Jacobs, J. Am. Chem. Soc., 61, 2890 (1939); doi:10.1021/ja01265a088.

A. Zaman, M.A. Khan, M.A. Munawar, M. Athar, M. Pervaiz, A. Pervaiz and A. Mahmood, Asian J. Chem., 27, 2823 (2015); doi:10.14233/ajchem.2015.18094.

Issue

Vol. 28 No. 4 (2016): Vol 28 Issue 4

Mass Spectrometry of Substituted Ethyl-4-anilinopyrazolo[3,4-b]pyridine-5-carboxylates

Corresponding Author(s) : Samina Aslam

Abstract

Keywords

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