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Synlett 2018; 29(11): 1502-1504
DOI: 10.1055/s-0036-1591991
DOI: 10.1055/s-0036-1591991
letter
Synthetic Approach Toward Heterocyclic Hybrids of [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazines
Thanks are due to the University of Aveiro and FCT/MEC for financial support to the QOPNA research project (FCT UID/QUI/00062/2013), financed by national funds and, when appropriate, co-financed by FEDER under the PT2020 Partnership Agreement. Thanks are also due to the Portuguese NMR Network. We would also like to thank FCT/MEC and the General Directorate for Scientific Research and Technological Development – DGRSDT of Algeria and the Agence Thématique de Recherche en Sciences et Technologie ATRST for approving the co-financed bilateral project PT-DZ/0005.
Weitere Informationen
Publikationsverlauf
Received: 10. März 2018
Accepted: 24. März 2018
Publikationsdatum:
23. April 2018 (online)
Abstract
The synthesis of novel heterocyclic [1,2,4]triazolo[3,4-b][1,3,4]thiadiazine hybrids by a bimolecular reaction of 2-(4-amino-5-mercapto-4H-[1,2,4]triazol-3-yl)phenol with an aromatic or heterocyclic α-bromoacetyl derivatives is described. This synthetic procedure starts from an unprotected phenol.
Key words
triazolothiadiazines - triazolylphenol - bromomethyl ketones - polycycles - heterocycles - cyclizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591991.
- Supporting Information
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References and Notes
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- 8 [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazines 3a–e; General Procedure Equimolar amounts of the appropriate α-bromoacetyl derivative 2a–e (1.0 mmol) and triazolylphenol 1 (0.2 g; 1.0 mmol) were dissolved in absolute EtOH (10 mL) containing a catalytic amount of AcOH (1 mL), and the mixture was heated for 2 h, then cooled to r.t. The resulting solid was collected by filtration and washed with EtOH and Et2O to give the pure product.
- 9 7-Hydroxy-3-[3-(2-hydroxyphenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-2H-chromen-2-one (3b) C19H12N4O4S. Green solid; yield: 0.23 g (60%); mp 239–241 °C. 1H NMR (400 MHz, DMSO-d 6): δ = 5.00 (s, 2 H, H-7′), 6.80 (d, J = 2.2 Hz, 1 H, H-8), 6.89 (dd, J = 8.6, 2.2 Hz, 1 H, H-6), 6.93–7.01 (m, 1 H, H-5′′), 7.06 (dd, J = 8.3, 0.7 Hz, 1 H, H-3′′), 7.41–7.46 (m, 1 H, H-4′′), 7.71 (dd, J = 7.8, 1.7 Hz, 1 H, H-6′′), 7.85 (d, J = 8.6 Hz, 1 H, H-5), 8.77 (s, 1 H, H-4), 10.23 (s, 1 H, 2′′-OH), 11.33 (s, 1 H, 7-OH). 13C NMR (100 MHz, DMSO-d 6): δ = 44.0 (C-7′), 102.4 (C-8), 110.0 (C-1′′), 111.4 (C-4a), 115.1 (C-6), 117.7 (C-3′′), 117.9 (C-3), 120.1 (C-5′′), 129.3 (C-6′′), 133.6 and 133.7 (C-4′′ and C-5), 149.9 (C-4), 156.5 (C-2′′), 158.0 (C-8a), 159.6 (C-2), 163.3 (C-8′a), 164.9 (C-3′, C=N), 165.4 (C-7), 189.9 (C-6′, C=N). HRMS-ESI+: m/z [M + H]+ calcd for C19H13N4O4S: 393.0658; found: 393.0677.