Abstract
The communication deals with the eco-friendly synthesis and X-ray crystal structure of an organic carbonitrile, namely 6-amino-3-phenyl-4-(pyridin-4-yl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile. The title compound was synthesized in 89% yield by following a simple, straightforward and highly efficient multicomponent one-pot protocol under the excellent catalytic influence of non-toxic trisodium citrate dihydrate under ambient conditions. X-ray diffraction studies reveal the packing of molecules in the crystal, which is strongly influenced by both intra and intermolecular hydrogen interactions. In addition, aromatic π–π interactions stabilize the molecular chains propagating along [001].
Similar content being viewed by others
REFERENCES
J. L. Wang, D. Liu, Z. J. Zhang, et al., Proc. Natl. Acad. Sci. USA 97, 7124 (2000).
M. B. Hogale and B. N. Pawar, J. Ind. Chem. Soc. 66, 206 (1989).
E. H. El-Tamany, F. A. El-Shahed, and B. H. Mohamed, J. Serb. Chem. Soc. 64, 9 (1999).
M. E. A. Zaki, H. A. Soliman, O. A. Hiekal, and A. E. Rashad, Z. Naturforsch C 61, 1 (2006).
M. Kasiotis, E. N. Tzanetou, S. A. Haroutounian, Front. Chem. 2, 1 (2014).
F. M. Abdelrazek, P. Metz, O. Kataeva, et al., Arch. Pharm. 340, 543 (2007).
E. M. Kassem, E. R. El-Sawy, H. I. Abd-Alla, et al., Egypt Pharm. J. 11, 116 (2002).
A. H. Mandour, E. R. El-Sawy, M. S. Ebaid, and S. M. Hassan, Acta Pharm. 62, 15 (2012).
N. Foloppe, L. M. Fisher, R. Howes, et al., Bioorg. Med. Chem. 14, 47922 (2006).
S. Bhavanarushi, V. Kanakaiah, E. Yakaiah, et al., Med. Chem. Res. 22, 2446 (2013).
K. E.-D. El-Ansary, A. T. Taher, A. A. E.-H. El-Rahmany, and S. E. Awdan, J. Am. Sci. 10, 284 (2014).
G. Brahmachari and B. Banerjee, Asian J. Org. Chem. 5, 271 (2016).
Oxford Diffraction, CrysAlis PRO (Oxford Diffraction Ltd, Yarnton, Oxfordshire, England, 2010).
G. M. Sheldrick, Acta Crystallogr. A 64, 112 (2008).
A. L. Spek, Acta Crystallogr. D 65, 148 (2009).
M. Nardelli, J. Appl. Crystallogr. 28, 659 (1995).
N. Sharma, G. Brahmachari, B. Banerjee, et al., Acta Crystallogr. E 70, o875 (2014).
N. S. Topno, K. Kumaravel, M. Kannan, et al., Acta Crystallogr. E 67, o956 (2011).
S. Yousuf, H. Bano, M. T. Muhammad, and K. M. Khan, Acta Crystallogr. E 71, o453 (2015).
W. L. Duax and D. A. Norton, Atlas of Steroid Structure (Plenum, New York, 1975), Vol. 1.
A. Lorente, C. Galan, I. Fonseea, and J. Sanz-Aparicio, Can. J. Chem. 73, 1546 (1995).
F. H. Allen, O. Kennard, D. G. Watson, et al., J. Chem. Soc. Perkin Trans. 2, S1 (1987).
C. F. Macrae, P. R. Edgington, P. MacCabe, et al., J. Appl. Crystallogr. 39, 453 (2006).
Funding
GB is thankful to CSIR, New Delhi, for financial support.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Sharma, S., Brahmachari, G. & Gupta, V.K. X-Ray Crystal Structure Analysis of Novel 6-Amino-3-Phenyl-4-(Pyridin-4-yl)-2,4-Dihydropyrano[2,3-c]pyrazole-5-Carbonitrile. Crystallogr. Rep. 65, 1202–1207 (2020). https://doi.org/10.1134/S1063774520070184
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1063774520070184