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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Developing Multi-kilogram Continuous Flow Cyclopropanation

Following reaction optimisation using a FlowSyn, a convenient and high yielding flow cyclopropanation process using EDSA following by a base mediated isomerisation was developed to afford trans-(dioxo)-azabicyclo-[3.1.0]-hexane carboxylate

Efficient controlled mixing was shown to be a key requirement to obtain a high yield and minimise side-product formation.

In this way, the reaction yield was increased significantly under flow conditions in comparison to batch and the robustness and reproducibility of the process was demonstrated by the synthesis of this key intermediate on a multi-kilogram scale.

 

F. G. Buono, M. C. Eriksson, B.-S. Yang, S. R. Kapadia, H. Lee, J. Brazzillo, J. C. Lorenz, L. Nummy, C. A. Busacca, N. Yee , C. Senanayake, Org. Process Res. Dev., 2014, 18 (11), pp 1527–1534