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Nucleophilic Reaction Lab Report

Decent Essays

March 2017 Selective Synthesis Dispiro[indoline-3,2′-pyrrolidine-3′,3″-quinoline]
Derivatives and Spiro[imidazole-4,3′-quinoline] Derivatives via

1,3-Dipolar Cycloaddition Reaction

859

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niv am cem
02/
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e-3 de cycloadditio

structure 4

The target compound 7 was prepared by adding the re- ortion. The poxide for-

ave methyl
© 2016 Wiley Periodicals, Inc. nitrogen atom from sarcosine and carbonyl of isatin, 4-hydroxy-7-methoxy-2-oxo-1,2-dihydroquinoline-3-carbo for this reaction, leading to the formed spiro
. The nucleophilic reaction between the

Moreover, the treatment of compound 9 w disulphide in the presence of dimethylsulphate g
Chemistry. The 1,3-dipolar cycloaddition reaction of azomethine ylide b with dipolarophile 3 yielded …show more content…

We try to synthesize
5′-(4-hydroxy-7-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)-
3′H-spiro[indoline-3,2′-(1,3,4)thiadiazol]-2-one (12) by heating compound 11 with isatin according to literature procedure [18], but this attempt was unsuccessful
(Scheme 3).Figure 1.

13C NMR of compounds 4 and 11.

Scheme 1. Synthesis of 7″-methoxy-4′-(4-methoxyphenyl)-1′-methyl-2″H-dispiro[indoline-3,2′-pyrrolidine-3′,3″-quinoline]-2,2″,4″(1″H)-trione (4).

Scheme 2. Mechanism of formation of 2-amino-7′-methoxy-5-(4-methoxyphenyl)-2′H-spiro[imidazole-4,3′-quinoline]-2′,4′(1′H)-dione (7).

860 W. S. Hamama, A. E. E. Hassanien, M. G. El-Fedawy, and H. H. Zoorob Vol 54

Journal of Heterocyclic Chemi stry DOI 10.1002/jhet

parameters such as heat of formation, electronic energy, nu- clear energy, and dipole moment.

EXPERIMENTAL

Scheme 3. Synthesis of 4-hydroxy-7-methoxy-2-oxo-1,2-dihydroquinoline-3-carbothiohydrazide (11).

Figure 2. Optimum geometry of intermediate b. [Color figure can be viewed at wileyonlinelibrary.com]

March 2017 Synthesis of Dispiro Spiro Quinoline Derivatives …show more content…

Anal. for C28H25N3O5 (483.18): Calcd: C
69.55, H 5.21, N 8.69%. Found: C 69.59, H 5.19, N 8.50%.

2-Amino-7′-methoxy-5-(4-methoxyphenyl)-2′H-spiro[imidazole-
4,3′-quinoline]-2′,4′ (1′H)-dione (7). A mixture of 3 (1.0 g,
3.23mmol), H2O2 (0.37mL, 30%), and ethanol (20mL) was stirred at room temperature then added guanidine nitrate (0.59 g, 4.83mmol) and aqueous solution of KOH
(50%) (1.30mL) were stirred at 80°C for 2 h. The ethanol was evaporated, and water (30mL) was added to the reaction mixture remainder. The outcome product was filtered off, washed accurately with water. The wet product slightly still wet filter cover was mixed with ethanol (10mL), and the resulted suspension refluxed for
30min. After cooling, the precipitate was filtered off, washed with ethanol, and finally dried.
Yellow crystals (0.35 g, 30%), mp 196–197°C (DMF/

H2O); Rf = 0.63 [ethyl acetate: pet. ether (40:60)](1.5:4);
IR(KBr): γ/cm�1 = 3327 (NH2), 3267 (NH), 1658 (CO),
1612 (CONH); 1H NMR (CDCl3): δ: 3.72 (s, 3H, OCH3- quinolone), 3.83 (s, 3H, OCH3-aromatic), 6.77–6.89 (m,
7H, aromatic-CH), 7.87 (broad s, 1H, NH, D2O exchange- able), 9.83 (broad s, 2H, NH2, D2O exchangeable);

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