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Synthesis of 2,6-diaminopyridine substituted α-oxoketene S,N-acetals: Crystal structure and hydrogen bonding interactions

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Abstract

Polyaza α-oxoketene S,N-acetals can exist as either enamino or imino tautomeric forms. Based on the spectroscopic data and structural analysis of one of the S,N-acetals, the stereochemistry was unambiguously assigned as an all-E-configuration. The crystal structure confirms the enamino structure and shows extensive use of C-H⋯X (X = N, O, and S) weak hydrogen bonding interactions, thereby generating a 3-dimensional network in solid state.

A new series of polyaza α-oxoketene S,N- acetals 3a-d was synthesized by thiomethyl displacement of α-oxoketene dithioacetals 2a-d with lithiated 2,6-diaminopyridine in good yields. The rotameric conformations and hydrogen bonding interactions are discussed with crystal structure.

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Acknowledgements

Financial supports from the Council of Scientific and Industrial Research (CSIR), India (project No. 01(2387)/10/EMR-II) and the Department of Science and Technology (DST), India (project No. SR/S1/OC-31/2009) are gratefully acknowledged. We thank Atta M Arif (University of Utah, USA) for crystal structure analysis. We also thank (SAIF), (CDRI), Lucknow and SAIF, NEHU, Shillong for the spectral recordings.

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Authors and Affiliations

  1. Department of Chemistry, Manipur University, Canchipur, 795 003, India

    OKRAM MUKHERJEE SINGH & LAISHRAM RONIBALA DEVI

  2. Department of Chemistry, Indian Institute of Technology Patna, Patna, 800 013, India

    NEELADRI DAS

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  1. OKRAM MUKHERJEE SINGH
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  2. LAISHRAM RONIBALA DEVI
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Correspondence to OKRAM MUKHERJEE SINGH.

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Supplementary information

CCDC-749446 (3b) contains the supplementary crystallographic data for this article. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data_request/cif.

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SINGH, O.M., DEVI, L.R. & DAS, N. Synthesis of 2,6-diaminopyridine substituted α-oxoketene S,N-acetals: Crystal structure and hydrogen bonding interactions. J Chem Sci 125, 1103–1107 (2013). https://doi.org/10.1007/s12039-013-0488-5

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