Solvent‐free neat synthetic route to tetrahydroacridinones

Kidwai, Mazaahir; Rastogi, Shweta

doi:10.1002/hc.20080

Cited by 23 publications

(8 citation statements)

References 20 publications

(19 reference statements)

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“…For the biological and physical activity of compounds containing the acridine skeleton, see: Wysocka-Skrzela & Ledochowski (1976); Matsumoto et al (1983); Popielarz et al (1997). Jia et al (2007); Kidwai & Rastogi (2005); Srividya et al (1996). For microwave irradiation in organic synthesis, see: Tu et al (2002Tu et al ( , 2004.…”

Section: Related Literaturementioning

confidence: 99%

“…We have already reported the synthesis of heterocyclic compounds under microwave irradiation (Tu et al 2004). M. Kidwai and S. Rastogi have reported the synthesis of polyhydroacridinones without additional fused benzene rings (Kidwai et al 2005). The efficiency of microwave irradiation in promoting organic reaction and the success of its application in heterocyclic synthesis (Jia et al 2007) has rapidly gained in popularity.…”

Section: S1 Commentmentioning

confidence: 99%

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9,9-Dimethyl-12-(3-nitrophenyl)-7,8,9,10,11,12-hexahydrobenz[a]acridin-11-one

Jia¹,

Peng²,

2009

Acta Cryst E

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Section: Related Literaturementioning

confidence: 99%

Section: S1 Commentmentioning

confidence: 99%

9,9-Dimethyl-12-(3-nitrophenyl)-7,8,9,10,11,12-hexahydrobenz[a]acridin-11-one

Jia¹,

Peng²,

2009

Acta Cryst E

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“…The effectiveness of lasing can be controlled by substituents at the 9‐ and 10‐positions of the acridine chromophore [6]. Therefore, acridinediones with substituents at 9‐ or 10‐positions have already been synthesized by using different methods [7–13]. Photochemical properties of some acridinedione dyes were reported in literature [14–16].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and laser activity of halo‐acridinedione derivatives

Kaya

Yıldırır

Türker

2009

Journal of Heterocyclic Chem

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magnified imageSynthesis of 10‐(halophenyl)‐9‐(4‐methoxyphenyl)‐3,4,6,7,9,10‐hexahydroacridine‐1,8‐(2H,5H)‐dione derivates have been prepared and their absorption, emission, and laser properties have been evaluated. The structures of all the synthesized compounds were characterized by spectroscopic methods IR, 1H NMR, 13C‐APT, MS, and elemental analysis. J. Heterocyclic Chem., (2009).

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“…[5][6][7] Many studies have been carried out on acridine derivatives, in particular, how to modify the 9-and 10-positions of the acridine cores. [8][9][10][11][12][13][14][15] Many methods have been developed for the preparation of acridine derivatives including the synthesis of the intermediates and changes of catalyst. [16][17][18][19][20][21] We now report a new series of 10-substituted 3,6-diphenyl-9aryl-3,4,6, 7,9,10-hexahydroacridine-1,8(2H,5H)-dione derivatives.…”

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Synthesis of 10-Substituted 3,6-Diphenyl-9-Aryl-3,4,6,7,9,10-Hexahydroacridine-1,8(2H,5H)-Dione Derivatives

Wang¹,

Bao

et al. 2015

Journal of Chemical Research

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Acridine derivatives include many bioactive compounds, which were widely used as antibacterial, 1 anti-inflammatory, 2 antimalarial, deworming, antitumour, 3,4 anti-blood-sucking insects and memory enhancement agents. [5][6][7] Many studies have been carried out on acridine derivatives, in particular, how to modify the 9-and 10-positions of the acridine cores. [8][9][10][11][12][13][14][15] Many methods have been developed for the preparation of acridine derivatives including the synthesis of the intermediates and changes of catalyst. [16][17][18][19][20][21] We now report a new series of 10-substituted 3,6-diphenyl-9aryl-3,4,6, 7,9,10-hexahydroacridine-1,8(2H,5H)-dione derivatives. They were synthesised from 5-phenylcyclohexane-1,3-dione, aromatic aldehydes and different amines in two steps. Results and discussionAs shown in the Scheme 1, compounds 1a-d were first obtained by reacting 5-phenylcyclohexane-1,3-dione with aromatic aldehydes in methanol/ethanol (1:1) mixture with good yields and high purity, catalysed by trace l-proline at room temperature for about 4h. The product was reacted with different amines, such as ammonium acetate, aniline, p-chloroaniline and naphthylamine, to prepare compounds 2a-n by refluxing in acetic acid. The crude products were purified by column chromatography with the eluent ethyl acetate/cyclohexane (1:5). The melting points and yields of compounds 1 and 2 are shown in Table 1.All data of MS, IR, 1 H NMR and elemental analysis shown in the experimental section, confirmed the compounds structures. The 1 H NMR data of compounds 1a-d revealed there was a multiplet signal for one proton at δ 7.01-7.14, which were different to the data of 2a-n and can be attributed to the peak of hydroxyl group at 10a-position. The peaks at δ 3.99-5.52 were the characteristic proton shifts of the 9-position, which also existed in 1 H NMR data of compounds 2a-n. They were influenced by aryl group and cyclohexene groups nearby. In all their IR spectra, the absorption bands around 1632-1648 cm -1 can be ascribed to ν (C=O), accordingly. However, there also existed broad absorption bands around 3370-3418 cm -1 in IR spectra of 1a-d that may be ascribed to ν (O-H), which was not found in the IR spectra of 2a-n.We also obtained the single crystal of 1b and its molecular structure was confirmed by the single-crystal X-ray diffraction analysis. The ORTEP diagram in Fig. 1 shows that a threemembered xanthene ring formed with the hydroxyl group at the 10a-position and benzyl ring at 9-position in compound 1b. That confirmed the analysis results of the spectra.

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Solvent‐free neat synthetic route to tetrahydroacridinones

Cited by 23 publications

References 20 publications

9,9-Dimethyl-12-(3-nitrophenyl)-7,8,9,10,11,12-hexahydrobenz[a]acridin-11-one

9,9-Dimethyl-12-(3-nitrophenyl)-7,8,9,10,11,12-hexahydrobenz[a]acridin-11-one

Synthesis and laser activity of halo‐acridinedione derivatives

Synthesis of 10-Substituted 3,6-Diphenyl-9-Aryl-3,4,6,7,9,10-Hexahydroacridine-1,8(2H,5H)-Dione Derivatives

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