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Synthesis and Structures of 3-Ethyl 1,2-Dimethyl 5-Chloroindolizine-1,2,3-Tricarboxylate and 3-Ethyl 1,2-Dimethyl 5-Bromoindolizine-1,2,3-Tricarboxylate from 2-Chloro-1-(2-Ethoxy-2-Oxoethyl)Pyridin-1-Ium Bromide

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Abstract

In this title compounds 3-ethyl 1,2-dimethyl 5-chloroindolizine-1,2,3-tricarboxylate 3 and 3-ethyl 1,2-dimethyl 5-bromoindolizine-1,2,3-tricarboxylate 4, there are two molecules in the asymmetric unit. This crystal was prepared by one-pot multicomponent reaction of 2-chloro-1-(2-ethoxy-2-oxoethyl)pyridin-1-ium bromide salt 1 with dimethyl acetylenedicarboxylate 2 in the presence triethylphosphite at room temperature in high yield. The indolozine products were confirmed with IR, mass, 1H, and 13C NMR. X-ray crystallographic technique was also conducted and the result showed the crystal belong to monoclinic system, space group pbca with a = 17.6696(7), b = 7.9336(3), c = 23.2275(9)Å, v = 3093.1(2)Å3, D c  = 1.521 mg/m3, µ = 0.31 mm−1. In both compounds no typical hydrogen bonding interactions could be located.

Graphical Abstract

Synthesis, and crystal structure of two 3-ethyl 1,2-dimethyl 5-chloroindolizine-1,2,3-tricarboxylate and 3-ethyl 1,2-dimethyl 5-bromoindolizine-1,2,3-tricarboxylate are reported.

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Acknowledgments

We acknowledge the financial support of Islamic Azad University, Bushehr Branch.

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Authors and Affiliations

  1. Chemistry Department, Bushehr Branch, Islamic Azad University, PO Box 7519619555, Bushehr, Iran

    Gholamhossein Khalili, Farzaneh Farid Ghiasi, Seyed Abolghasem Hashemi & Hamed Ghaedi

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  1. Gholamhossein Khalili
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  2. Farzaneh Farid Ghiasi
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  3. Seyed Abolghasem Hashemi
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  4. Hamed Ghaedi
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Correspondence to Gholamhossein Khalili.

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Khalili, G., Ghiasi, F.F., Hashemi, S.A. et al. Synthesis and Structures of 3-Ethyl 1,2-Dimethyl 5-Chloroindolizine-1,2,3-Tricarboxylate and 3-Ethyl 1,2-Dimethyl 5-Bromoindolizine-1,2,3-Tricarboxylate from 2-Chloro-1-(2-Ethoxy-2-Oxoethyl)Pyridin-1-Ium Bromide. J Chem Crystallogr 46, 341–344 (2016). https://doi.org/10.1007/s10870-016-0663-x

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  • DOI: https://doi.org/10.1007/s10870-016-0663-x

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