2,5-Bis(morpholinomethyl)furan

2,5-Bis(morpholinomethyl)furan, 11

Yield 98%, 1H NMR (CDCl3) = 6.13 (s, 2H), 3.70 (m, 8H), 3.51 (s, 4H), 2.45 (m, 8H);

13C NMR (CDCl3) = 150.9, 109.7, 66.8, 55.3, 53.2 ppm.

 m/z HRMS (ESI) Calcd. for C14H22N2O3 [M+H]: 267.1703. Found 267.1703.

Efficient route for the construction of polycyclic systems from bioderived HMF 

Green Chem., 2017, Advance Article
DOI: 10.1039/C7GC02211E, Paper

F. A. Kucherov, K. I. Galkin, E. G. Gordeev, V. P. Ananikov
Efficient one-pot synthesis of tricyclic compounds from biobased 5-hydroxymethylfurfural (HMF) is described using a [4 + 2] cycloaddition reaction.

Efficient route for the construction of polycyclic systems from bioderived HMF

F. A. Kucherov,^a  K. I. Galkin,^a  E. G. Gordeev^a  and  V. P. Ananikov*^a 

 Author affiliations

*Corresponding authors

^aZelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow 119991, Russia
E-mail: val@ioc.ac.ru
Web: http://AnanikovLab.ru

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Recent Developments in Chemistry of Phthalazines

From hydrazine and hydrazine derivatives

Hydrazine and hydrazine derivatives are the most common reagents used for the synthesis of phthalazinone derivatives via their reactions with phthalic anhydride, phthalides, phthalimides etc.

Hydrazines with anhydrides: Several methods were reported for the preparation of phthalazinones derivatives. These methods mainly involve the reaction of phthalic anhydrides with hydrazine hydrate in the presence of acetic acid [42-44].

Phthalazinones 5,7-9 were synthesized from commercially available phthalic anhydride in 2-3 steps as depicted in (Scheme 1 and 2) [45-51].

Additionally, reaction of phthalic anhydride and aromatic hydrocarbons in the presence of anhydrous aluminum chloride under Friedel-Craft’s conditions afforded 2-aroylbenzoic acids 10 which treated with hydrazine hydrate and hydrazine derivatives to give the phthalazine (2H)-1-one 11,12 [52-57] (Scheme 3).

Recent Developments in Chemistry of Phthalazines
Fatma SM Abu El-Azm*, Mahmoud R Mahmoud, and Mohamed H Hekal
Chemistry Department, Faculty of Science, Ain Shams University, Abbassia, Cairo, Egypt
Corresponding Author :	Fatma SM Abu El-Azm Chemistry Department Faculty of Science Ain Shams University, Abbassia Cairo, Egypt, Post code 11566 Tel: 0201220383276 E-mail: ftmsaber@yahoo.com
http://www.omicsonline.org/open-access/recent-developments-in-chemistry-of-phthalazines-2161-0401.1000132.php?aid=40611
Citation: El-Azm FSMA, Mahmoud MR, Hekal MH (2015) Recent Developments in Chemistry of Phthalazines. Organic Chem Curr Res 4:132. doi: 10.4172/2161-0401.1000132

Chemistry Department
Faculty of Science
Ain Shams University, Abbassia
Cairo, Egypt








/////Phthalazine derivatives,  Pyrazolophthalazines,  Indazolophthalazines,  [1,2,4] Triazolophthalazines, Fatma SM Abu El-Azm

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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