Novel 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine bearing substituted phenylquinolin-2-one moiety

Figure 1.

General structure of final synthesized derivatives.

Scheme 1. 

Synthetic Scheme for 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine bearing substituted phenylquinolin-2-one (4a–4t). Where R = H, 2-Br, 3-Br, 4-Br, 2-Cl, 3-Cl, 4-Cl, 2-F, 3-F, 4-F, 2-NO₂, 3-NO₂, 4-NO₂, 2-CH₃, 3-CH₃, 4-CH₃, 2-OCH₃, 3-OCH₃, 4-OCH₃, 3,4,5-t-OCH₃. Reagents and conditions: (a) C₂H₅OH, Nitrobenzene, Con. H₂SO₄, reflux, 80 °C, 4 h; (b) chloroacetic acid, NaHCO₃, water, CuO, reflux, 80 °C, 5 h; (c) thiocarbohydrazide, Δ, 2 h; (d) phenacyl bromide, anhydrous ethanol, NH₄OH, 50 °C, 6 h.

 In the present work twenty derivatives of phenylquinoline-1,2,4-triazolothiadiazines were synthesized. The structures of the synthesized compounds were established by spectral data. According to IR spectroscopic data compounds (4a–4t) showed peaks at 1306–1330 cm⁻¹, 650–682 cm⁻¹ due to -NC and CSC stretching vibrations respectively and no absorption peaks at 3140–3280 cm⁻¹, 3050–3090 cm⁻¹ due to -NH₂ and -SH groups respectively indicated smooth cyclization of triazoles leading to the formation of thiadiazine ring. Further, ¹H NMR spectra of the synthesized compounds were confirmed by the appearance of SCH₂ proton of 1,3,4-thiadiazine ring at 4.40–4.54 ppm and CH₂ proton at 5.97–6.20 ppm as broad singlet. All other aromatic protons were observed at expected region. Mass spectra (ESI-MS) of all the synthesized compounds showed molecular ion [M + H]⁺ peak in agreement with their molecular formula. Physical and elemental analyses are listed in Table 1.

2.6.20. 6,7,8-Trimethoxy-4-phenyl-1-({6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl}methyl)-1,2-dihydroquinolin-2-one (4t)

White needle Crystal; IR (KBr, cm⁻¹): 3023 (Ar CH str), 2901 (Aliphatic CH str),1706 (CO str), 1620 (CN str), 1564 (CC str), 1330 (Ar CN str), 683 (CSC); ¹H NMR (CDCl₃, 300 MHz): δ (ppm): 3.84 (s, 9H, 3xOCH₃), 4.51 (s, 2H, SCH₂), 5.98 (s, 2H, CH₂), 6.85 (s, 1H, CH), 7.45(d, 2H, J = 8.5 Hz, ArH), 7.48(m,5H, ArH), 7.74 (q, 4H, ArH). ESI-MS (m/z) calcd. is 539.6, found 540.7 [M + H]⁺; anal. calcd. for C₂₉H₂₅N₅O₄S (539.60): C 64.55, H 4.67, N 12.98; found: C 64.54, H 4.63, N 12.95.

 Arabian Journal of Chemistry
 

Available online 11 July 2015

In Press, Corrected Proof — Note to users

ORIGINAL ARTICLE

Synthesis, characterization and antimicrobial evaluation of some novel 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine bearing substituted phenylquinolin-2-one moiety

• Swagatika Ghosh^a, ,
• Amita Verma^{a, ,} ,
• Alok Mukerjee^b,
• Milan Kumar Mandal^a

• ^a Department of Pharmaceutical Sciences, Faculty of Health Sciences, Allahabad, Uttar Pradesh 211007, India
• ^b Department of Pharmaceutical Chemistry, United Institute of Pharmacy, UPSIDC, Naini, Allahabad, Uttar Pradesh 211010, India

Received 3 April 2014, Accepted 7 July 2015, Available online 11 July 2015

Open Access funded by King Saud University

Under a Creative Commons license

http://www.sciencedirect.com/science/article/pii/S187853521500218X

doi:10.1016/j.arabjc.2015.07.003

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Renewable conjugated acids as curatives for high-performance rubber/silica composites

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Sulphur-cured diene-based rubbers generally suffer from insufficient anti-ageing properties, and the curing process involves the use of toxic additives. Renewable conjugated acids are demonstrated to effectively cure epoxidized natural rubber into a high-performance elastomer, without the use of any toxic accelerators or antioxidants.

Renewable conjugated acids as curatives for high-performance rubber/silica composites

Tengfei Lin,^a   Xuhui Zhang,^a   Zhenghai Tang^a and   Baochun Guo*^a  

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*Corresponding authors

^aDepartment of Polymer Materials and Engineering, South China University of Technology, Guangzhou, P. R. China
E-mail: psbcguo@scut.edu.cn
Fax: +86 20 22236688
Tel: +86 20 87113374

Green Chem., 2015,17, 3301-3305

 

http://pubs.rsc.org/en/content/articlelanding/2015/gc/c5gc00834d#!divAbstract
DOI: 10.1039/C5GC00834D
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Hispidin

Hispidin

 

6-(3,4-dihydroxystyryl)-4-hydroxy-2-pyrone

cosy, hsqc, ftir seehttp://www.uvu.edu/chemistry/docs/research/hispidin.pdf

HMBC

FTIR

HSQC

http://www.uvu.edu/chemistry/docs/research/hispidin.pdf

Details
	Spectral Data Additional Data Download Type: 13C Atom No. ⇓ Mult.(coupling const.) Meas. Shift CSEARCH-Prediction 0 1 D 134.81 134.2 2 D 120.91 121.2 3 D 116.65 116.8 4 D 115.53 116.4 5 D 113.89 114.6 6 D 100.14 101.6 7 D 89.93 94.5 8 S 127.99 127.6 9 S 169.85 161.8 10 S 160.35 158.3 11 S 146.70 148.4 12 S 145.52 147.1 13 S 162.82 169.2 Spectral Data Additional Data Download Type: 1H Atom No. ⇓ Mult.(coupling const.) Meas. Shift Intensity 1-H 7.29 (H 19) 1.0 2-H 6.88 (H 21) 1.0 3-H 6.69 (H 20) 1.0 4-H 6.91 (H 22) 1.0 5-H 7.17 (H 23) 1.0 6-H 6.13 (H 24) 1.0 7-H 5.37 (H 25) 1.0 14-H 15-H 16-H

 1H NMR PREDICT

13C NMR PREDICT

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