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Convenient one-pot access to novel densely functionalized pyrano[2,3-d][1,3,4]thiadiazolo[3,2-a]pyrimidines via three component reaction

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Abstract

In this work, an efficient isocyanide-based three component method is developed for the synthesis of the novel substituted pyrano[2,3-d][1,3,4]thiadiazolo[3,2-a]pyrimidine system, having both the biologically active pyranopyrimidine and thiadiazolopyrimidine scaffolds, from the readily attainable reaction of 7-hydroxy-2-phenyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidine-5-one, isocyanides, and dialkylacetylenedicarboxylates. This procedure has the chief advantages of fairly high reaction yields, mild reaction conditions, high atom-economy, and catalyst-free reaction.

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Fig. 1
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Notes

  1. Single-Crystal X-ray data for 4a (CCDC 151190): C24H24N4O6S: MW = 496.53, Monoclinic, space group P21, cell dimensions a = 10.1483 (8) Å, b = 17.5745 (14) Å, c = 12.6336 (11) Å, β = 93.342 (1)°, V = 2249.4 (3) Å3, Z = 4, Dx = 1.466 Mg m−3, F000 = 1040, crystal size 0.32 × 0.31 × 0.31 mm, Crystallographic data were collected on a Bruker Smart APEX CCD diffractometer Kα radiation (λ = 0.71073 Å). A total of 43,168 reflections (2 ≤θ ≤ 29.4) were collected at a temperature of 100(2) K in a series of ω scans in 1° oscillations and integrated using the Stoe X-AREA software package (5031 reflections were unique with I > 2σ(I)). The structure was solved by direct method and subsequent different Fourier maps and then refined on F2 by a full-matrix least-square procedure using anisotropic displacement parameters. All non-H atoms were refined anisotropically and H-atoms were placed in the ideal positions. Final residuals were R = 0.039 and Rw = 0.

  2. Single-Crystal X-ray data for 4d (CCDC 1524054): C28H34N4O6S: MW = 554.65, Monoclinic, space group P21, cell dimensions a = 8.2682 (3) Å, b = 20.2332 (7) Å, c = 17.1811 (6) Å, α = 90 °, β = 102.056(1)°, γ = 90 °, V = 2810.87(17) Å3, Z = 4, Dx = 1.311 Mg m−3, F000 = 1176 , crystal size 0.194 × 0.094 × 0.083 mm, Crystallographic data were collected on a Bruker D8 VENTURE PHOTON 100 CMOS diffractometer with graphite monochromated Cu Kα radiation (λ = 1.54178 Å). A total of 44,187 reflections (5.2651 ≤ θ ≤ 74.5595) were collected at a temperature of 150(2) K in a series of ω scans in 1° oscillations and integrated using the Stoe X-AREA software package (5031 reflections were unique with I > 2σ(I)). The structure was solved by direct method and subsequent different Fourier maps and then refined on F2 by a full-matrix least-square procedure using anisotropic displacement parameters. All non-H atoms were refined anisotropically and H-atoms were placed in the ideal positions. Final residuals were R = 0.0398 and Rw = 0.0979 for 5736 parameters.

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Acknowledegements

The Research Council of Ferdowsi University of Mashhad is acknowledged for financial support (Grant No. 3/41156).

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Authors and Affiliations

  1. Department of Chemistry, Ferdowsi University of Mashhad, Mashhad, Iran

    Maryam Akhavan, Abbas Ali Esmaeili & Mahdieh Zangouei

  2. Department of Chemistry, Tulane University, New Orleans, LA, USA

    Joel T. Mague

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  1. Maryam Akhavan
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  2. Abbas Ali Esmaeili
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  4. Joel T. Mague
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Correspondence to Abbas Ali Esmaeili.

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Akhavan, M., Esmaeili, A.A., Zangouei, M. et al. Convenient one-pot access to novel densely functionalized pyrano[2,3-d][1,3,4]thiadiazolo[3,2-a]pyrimidines via three component reaction. Res Chem Intermed 43, 4683–4696 (2017). https://doi.org/10.1007/s11164-017-2904-9

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