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Synthesis, Characterization and Structural Conformation Studies of 2-Amino-3-ethoxycarbonyl-4-(4′-methoxy Phenyl)-4H-pyrano-[3,2-c]-chromene-6-methyl-5-one

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Abstract

2-amino-3-ethoxycarbonyl-4-(4′-methoxy Phenyl)-4H-pyrano-[3,2-c]-chromene-6-methyl-5-one was synthesized by the two-component reaction of 6-methyl-4-hydroxy coumarin with 4′-methoxy-2-cyano cinnamate, which was synthesized by Knoevenagel reaction with 88% yield. The compound obtained was characterized by spectroscopic techniques and confirmed by X-ray crystallographic studies. The crystallographic data analysis reveals that the title compound crystallizes in the triclinic space group \(P\overline{1}\) with cell parameters a = 7.7750(8) Å, b = 9.0310(6) Å, c = 15.6120(17) Å, α = 77.249(7)°, β = 115.860(3)°, γ = 70.139(7)°, V = 1,003.0(16) Å3 for Z = 4. The structure has been solved by direct methods and refined to R1 = 0.0552 for 3,164 observed reflections with I > 2 σ(I). The pyran ring is in a flattened boat conformation. The carbonyl group is oriented in a -synperiplanar(cis) conformation.

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Scheme 1
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Notes

  1. “CCDC 615274 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html (or from The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44-1223-336033. email: deposit@ccdc.cam.ac.uk”

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Acknowledgements

The authors would like to express their thanks to Department of Chemistry, Saurashtra University, Rajkot for the laboratory facility and DST, Government of India for financial assistance under the project SP/I2/FOO/93.

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Correspondence to M. Anandalwar Sridhar.

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Naveen, S., Lakshmi, S., Manvar, D. et al. Synthesis, Characterization and Structural Conformation Studies of 2-Amino-3-ethoxycarbonyl-4-(4′-methoxy Phenyl)-4H-pyrano-[3,2-c]-chromene-6-methyl-5-one. J Chem Crystallogr 37, 733–738 (2007). https://doi.org/10.1007/s10870-007-9241-6

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  • DOI: https://doi.org/10.1007/s10870-007-9241-6

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