Design, synthesis and antibacterial evaluation of 2-alkyl- and 2-aryl-3-(phenylamino)quinazolin-4(3H)-one derivatives

Ali Asghar Mohammadi; Reza Ahdenov; Ali Abolhasani Sooki

doi:10.1515/hc-2016-0201

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Design, synthesis and antibacterial evaluation of 2-alkyl- and 2-aryl-3-(phenylamino)quinazolin-4(3H)-one derivatives

Ali Asghar Mohammadi , Reza Ahdenov und Ali Abolhasani Sooki

Veröffentlicht/Copyright: 29. März 2017

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Abstract

2-Alkyl and 2-aryl-3-(phenylamino)quinazolin-4(3H)-ones 4a–h were synthesized in a one-pot three-component condensation of an isatoic anhydride 1a–h, ethyl or methyl ortho ester and phenylhydrazine in the presence of KAl(SO₄)₂·12H₂O (alum) as a nontoxic, reusable, inexpensive and easily available catalyst. The synthesis was conducted under microwave irradiation or classical heating. Products 4a and 4b show good antimicrobial activities.

Keywords: alum; antimicrobial activity; isatoic anhydride; ortho esters; quinazolin-4(3H)-one

Introduction

Quinazolin-4(3H)-one and its derivatives possess a wide spectrum of biological properties [1], [2], such as anti-inflammatory [3], antihypertensive [4], anti-HIV [5], anticancer [6], antiviral [7] and antibacterial activity [8]. In addition, these structural fragments are present in several bioactive natural products [9], [10], [11], such as l-vasicinone [12], chrysogine [13] and drugs [14] such as methaqualone [15], febrifugine and isofebrifugine [16], [17]. There are several methods in the literature for the preparation of quinazolin-4(3H)-ones [18], [19], [20], [21]. These are cyclocondensation of 2-aminobenzamides with acyclic or cyclic 1,3-diketones catalyzed by FeCl₃ [22], condensation of 2-halobenzamides (or 2-halonicotinamides), aldehydes and sodium azide catalyzed by copper [23], reaction of benzoxazinones with primary aliphatic and aromatic amines [24], reaction of 2-iodoanilines with trimethyl orthoformate and amines in the presence of palladium on activated charcoal (Pd/C) [25] and condensation of anthranilic acid with acyl chlorides and aromatic/aliphatic amines in acidic ionic liquids under microwave irradiation [26].

Results and discussion

Multicomponent reactions (MCRs) are powerful tools in the modern drug discovery process in terms of lead finding and lead optimization. Recently, we have reported the preparation of indenopyridine [27], bis[spiro(quinazoline-oxindole)] [28], bis-dihydroquinazolinone [29], 1′H-spiro[isoindoline-1,2′-quinazoline]-3,4′(3′H)-dione [30] and 2-aryl-3-(phenylamino)-2,3-dihydroquinazolin-4(1H)-one [31] via multicomponent reactions. Along this line, we have designed a three-component one-step synthesis of quinazolin-4(3H)-ones. The use of KAl(SO₄)₂·12H₂O (alum), which is relatively nontoxic and inexpensive, is the center of our study [32], [33].

The reaction of isatoic anhydride 1a, phenylhydrazine 2 and triethyl orthoformate 3a in ethanol in the presence of a catalytic amount of alum under reflux conditions was completed in 130 min. Workup of the mixture furnished 3-(phenylamino)quinazolin-4(3H)-one (4a) in an 89% yield (Scheme 1). Encouraged by this success, we extended this reaction of phenylhydrazine 2 with a range of isatoic anhydrides 1b–h and orthoesters 3b–h under similar conditions, furnishing the respective 3-(phenylamino)quinazolin-4(3H)-one 4b–h in good yields (Scheme 1). We then examined this reaction under microwave irradiation and found that it furnishes 3-(phenylamino)quinazolin-4(3H)-ones 4a–h in a much shorter time of 5 min. In order to increase the energy input and provide a uniform heating, a small amount of N,N-dimethylacetamide (DMAC), an excellent energy-transfer solvent with a high dielectric constant, was added to the reaction mixture. The structures of all products were fully consistent with IR, ¹H NMR, ¹³C NMR, MS and elemental analysis data.

Scheme 1

Synthesis of 3-(phenylamino)quinazolin-4(3H)-ones 4a–h.

The synthesized compounds were screened in vitro for their antibacterial activities against Gram-negative bacteria Escherichia coli, ATCC 25922, Pseudomonas aeruginosa, ATCC 85327, Klebsiella pneumonia, ATCC 29655 and Gram-positive bacteria Enterococcus faecalis, ATCC 29737, Bacillus subtilis ATCC 465, Bacillus pumilus PTCC 1114, Micrococcus luteus PTCC 1110, Staphylococcus aureus ATCC 25923, Staphylococcus epidermidis ATCC 12228 and Streptococcus mutans, PTCC 1601. Inhibition zones (IZ) were measured by the disk diffusion method [34] and, subsequently, the minimum inhibitory concentrations (MIC) were also obtained [35].

Activities of the compounds were compared with those of tetracycline and gentamicin used as standards. The screening results indicate that some of the tested compounds exhibit significant antibacterial activities. Compound 4a, unsubstituted at position 2 of the quinazoline moiety shows much better activity than the reference drugs. 2-Alkylquinazolines 4b–d exhibit good activity, while the remaining compounds generally show inferior activities against the tested bacterial strains.

Conclusions

This paper describes a convenient and efficient method for the synthesis of 2-alkyl and 2-aryl-3-(phenylamino)quinazolin-4(3H)-one derivatives through the three-component reaction of an isatoic anhydride, an ortho ester and phenylhydrazine using KAl(SO₄)₂·12H₂O (alum) as a heterogeneous catalyst. The method offers a high yield of products and an easy work-up and uses an inexpensive, non-toxic and easily available catalyst.

Experimental

Melting points were obtained in open capillary tubes on an Electrothermal 9200 apparatus. Electron-impact mass spectra were recorded at 70 eV on a Shimadzu QP 1100BX mass spectrometer. IR spectra were recorded in KBr pellets on a Shimadzu IR-470 spectrophotometer. ¹H NMR (300 MHz) and ¹³C NMR (75 MHz) spectra were determined on a Bruker 300 DRX Avance instrument. Elemental analyses for C, H and N were performed using a Heraus CHN rapid analyzer.

General procedures for the synthesis of 2-alkyl- and 2-aryl-3-(phenylamino)quinazolin-4(3H)ones 4a–h

Classical heating

A mixture of an isatoic anhydride (1, 1 mmol), phenylhydrazine (2, 2 mmol), an ortho ester (3, 2 mmol), alum (0.15 g) and EtOH (10 mL) was stirred and heated under reflux for a period of time indicated in Scheme 1. After completion of the reaction (monitored by TLC, ethyl acetate/n-hexane, 1/1), the mixture was concentrated under reduced pressure and the residue was treated with water (20 mL). The resultant solid was separated by filtration and crystallized from ethanol.

Microwave irradiation

A mixture of an isatoic anhydride (1, 1 mmol), phenylhydrazine (2, 1 mmol), an ortho ester 3 (2 mmol), alum (0.15 g) and five drops of N,N-dimethylacetamide (DMAC) was mixed thoroughly in a Pyrex test tube. The homogenized mixture was irradiated in a microwave oven in two stages, with a cooling period between the irradiations: 210 W for 3 min, cooling, then 360 W for 5 min. After cooling to room temperature, the mixture was treated with water (10 mL) and the resultant precipitate was filtered and crystallized from ethanol.

3-(Phenylamino)quinazolin-4(3H)-one(4a)

This compound was obtained in yields of 89% (heat) and 93% (MW) as a white powder; mp 164–166°C; (lit. [36]: mp 166–167°C, yield 59%).

2-Methyl-3-(phenylamino)quinazolin-4(3H)-one (4b)

This compound was obtained in yields of 90% (heat) and 95% (MW) as a white powder; mp 209–211°C; IR (ν/cm⁻¹): 3296, 1634, 1602(C=O); ¹H NMR (DMSO-d₆) δ 3.39 (s, 3H, CH₃), 6.65 (d, J=7.7 Hz, 2H, Ar), 6.83 (t, J=7.3 Hz, 1H, Ar), 7.19 (t, J=7.9 Hz, 2H, Ar), 7.50 (t, J =7.1 Hz, 1H, Ar), 7.67 (d, J=8.0 Hz, 1H, Ar), 7.84 (t, J=8.0 Hz, 1H, Ar), 8.09 (d, J =7.2 Hz, 1H, Ar), 9.13 (s, 1H, NH); ¹³C NMR (DMSO-d₆): δ 21.8, 112.8, 120.7, 121.5, 126.6, 126.9, 127.3, 129.6, 135.1, 147.22, 147.29, 158.1, 160.6; MS: m/z 251 (M⁺). Anal. Calcd for C₁₅H₁₃N₃O: C, 71.70; H, 5.21; N, 16.72. Found: C, 71.59; H, 5.11; N, 16.61.

2-Ethyl-3-(phenylamino)quinazolin-4(3H)-one (4c)

This compound was obtained in 85% (heat) and 91% (MW) yields as a white powder; mp 163–165°C; IR (ν/cm⁻¹): 3264, 1640, 1608(C=O); ¹H NMR (DMSO-d6): δ 1.24 (t, J=7.5 Hz, 3H, CH₃), 2.63–2.76 (m, 1H, CH), 2.89–2.99 (m, 1H, CH), 6.61(d, J=7.9 Hz, 2H, Ar), 6.82 (t, J=7.5 Hz, 1H, Ar), 7.18 (t, J=7.5 Hz, 2H, Ar), 7.50 (t, J=7.5 Hz, 1H, Ar), 7.69 (d, J=7.9 Hz, 1H, Ar), 7.83 (t, J=7.5 Hz, 1H, Ar), 8.06 (d, J =7.9 Hz, 1H, Ar), 9.12 (s, 1H, NH); ¹³C NMR (DMSO-d₆): δ 11.4, 27.1, 39.0, 112.8, 120.6, 121.4, 126.6, 126.9, 127.6, 129.6, 135.1, 147.1, 147.4, 160.6, 161.3; MS: m/z 265 (M⁺). Anal. Calcd for C₁₆H₁₅N₃O: C, 72.43; H, 5.70; N, 15.84. Found: C, 72.33; H, 5.58; N, 15.73.

3-(Phenylamino)-2-propylquinazolin-4(3H)-one (4d)

This compound was obtained in yields of 86% (heat) and 90% (MW) as a white powder; mp 160–162°C; IR (ν/cm⁻¹): 3311, 1648, 1607(C=O); ¹H NMR (DMSO-d₆): δ 0.93 (t, J=7.3 Hz, 3H, CH₃), 1.72–1.82 (m, 2H, CH₂), 2.61–2.71 (m, 1H, CH), 2.86–2.95 (m, 1H, CH), 6.61 (d, J=7.5 Hz, 2H, Ar), 6.82 (t, J=75 Hz, 1H, Ar), 7.18 (t, J=7.5 Hz, 2H, Ar), 7.50 (t, J=7.5 Hz, 1H, Ar), 7.69 (d, J=7.9 Hz, 1H, Ar), 7.84 (t, J=7.9 Hz, 1H, Ar), 8.06 (d, J=7.9 Hz, 1H, Ar), 9.11 (s, 1H, NH); ¹³C NMR (DMSO-d₆): δ 14.1, 20.1, 35.63, 112.8, 120.6, 121.5, 126.6, 126.9, 127.6, 129.6, 135.1, 147.1, 147.5, 160.3, 160.7; MS: m/z 279 (M⁺). Anal. Calcd for C₁₇H₁₇N₃O: C, 73.10; H, 6.13; N, 15.04. Found: C, 73.01; H, 6.01; N, 14.93.

2-Butyl-3-(phenylamino)quinazolin-4(3H)-one (4e)

This compound was obtained in yields of 82% (heat) and 88% (MW) as a white powder; mp 172–174°C; IR (ν/cm⁻¹): 3296, 1626, 1604(C=O); ¹H NMR (DMSO-d₆): δ 0.91(t, J=7.5 Hz, 3H, CH₃), 1.28–1.40 (m, 2H, CH₂), 1.69–1.77 (m, 2H, CH₂), 2.49 (m, 1H, CH), 2.71(m, 1H, CH), 6.61 (d, J=8.4 Hz, 2H, Ar), 6.82 (t, J=7.5 Hz, 1H, Ar), 7.20 (t, J=7.5 Hz, 2H, Ar), 7.49 (t, J=7.5 Hz, 1H, Ar), 7.68(d, J=8.0 Hz, 1H, Ar), 7.83 (t, J=8.0 Hz, 1H, Ar), 8.06 (d, J=7.9 Hz, 1H, Ar), 9.11 (s, 1H, NH); ¹³C NMR (DMSO-d₆): δ 14.1, 22.2, 28.8, 33.4, 112.8, 120.6, 121.5, 126.6, 126.9, 127.6, 129.6, 135.1, 147.1, 147.5, 160.6, 160.7; MS: m/z 293 (M⁺). Anal. Calcd for C₁₈H₁₉N₃O: C, 73.69; H, 6.53; N, 14.32. Found: C, 73.58; H, 6.40; N, 14.20.

2-Phenyl-3-(phenylamino)quinazolin-4(3H)-one (4f)

This compound was obtained in yields of 87% (heat) and 93% (MW) as a white powder; mp 185–187°C; IR (ν/cm⁻¹): 3253, 3028, 1675(C=O); ¹H NMR (DMSO-d₆): δ 6.57 (d, J=7.5 Hz, 2H, Ar), 6.75 (t, J=7.5 Hz, 1H, Ar), 7.11 (t, J=7.5 Hz, 2H, Ar), 7.38–7.44 (m, 3H, Ar), 7.58 (t, J=7.5 Hz, 1H, Ar), 7.73–7.81 (m, 3H, Ar), 7.91 (t, J=7.5 Hz, 1H, Ar), 8.13 (d, J=7.5 Hz, 1H, Ar), 9.10 (s, 1H, NH); ¹³C NMR (DMSO-d₆): δ 112.8, 114.7, 115.07, 117.8, 119.7, 126.8, 128.0, 128.7, 129.3, 134.2, 141.2, 147.3, 148.3, 163.0, 164.7; MS: m/z 313 (M⁺). Anal. Calcd for C₂₀H₁₅N₃O: C, 76.66; H, 4.82; N, 13.41. Found: C, 76.56; H, 4.70; N, 13.32.

6-Chloro-2-methyl-3-(phenylamino)quinazolin-4(3H)-one (4g)

This compound was obtained in yields of 81% (heat) and 88% (MW) as a white powder; mp 197–198°C; (lit. [37]: mp 195–196°C, yield 64%).

6-Chloro-2-ethyl-3-(phenylamino)quinazolin-4(3H)-one (4h)

This compound was obtained in yields of 80% (heat) and 90% (MW) yield as a white powder; mp 130–132°C; (lit. [37]: mp 131–131.5°C, yield 63%).

Acknowledgments

We are grateful to the Islamic Azad University, Sabzevar Branch, and the National Foundation Council Organization of the Islamic Republic of Iran for support.

References

[1] Baek, D. J.; Park, Y. K.; Il Heo, H.; Lee, M.; Yang, Z.; Choi, M. Synthesis of 5-substituted quinazolinone derivatives and their inhibitory activity in vitro. Bioorg. Med. Chem. Lett.1998, 8, 3287–3290.10.1016/S0960-894X(98)00602-7Suche in Google Scholar

[2] Hosseinzadeh, L.; Aliabadi, A.; Kalantari, M.; Mostafavi, A.; Khajouei, M. R. Synthesis and cytotoxicity evaluation of some new 6-nitro derivatives of thiazole-containing 4-(3H)-quinazolinone. Res. Pharm. Sci.2016, 11, 210–218.Suche in Google Scholar

[3] Alagarsamy, V.; Murugesan, S. Synthesis and pharmacological evaluation of some 3-(4-methoxyphenyl)-2-substituted aminoquinazolin-4(3H)-ones as analgesic and anti-inflammatory agents. Chem. Pharm. Bull.2007, 55, 76–80.10.1248/cpb.55.76Suche in Google Scholar PubMed

[4] Hussain, M. A.; Chiu, A. T.; Price, W. A.; Timmermans, P. B.; Shefter, E. Antihypertensive activity of 2[(2-hydroxyphenyl) amino]-4(3H)-quinazolinone. Pharm. Res.1988, 5, 242–244.10.1023/A:1015949931218Suche in Google Scholar

[5] Alagarsamy, V.; Murugesan, S.; Dhanabal, K.; Murugan, M.; De Clercq, E. Anti-HIV, antibacterial and antifungal activities of some novel 2-methyl-3-(substituted methylamino)-(3H)-quinazolin-4-ones. Ind. J. Pharm. Sci.2007, 69, 304–307.10.4103/0250-474X.33167Suche in Google Scholar

[6] Alafeefy, A. M.; Ashour, A. E.; Prasad, O.; Sinha, L.; Pathak, S.; Alasmari, F. A.; Rishi, A. K.; Abdel-Aziz, H. A. Development of certain novel N-(2-(2-(2-oxoindolin-3-ylidene)hydrazinecarbonyl)phenyl)-benzamides and 3-(2-oxoindolin-3-ylideneamino)-2-substituted quinazolin-4(3H)-ones as CFM-1 analogs: Design, synthesis, QSAR analysis and anticancer activity. Eur. J. Med. Chem.2015, 92, 191–201.10.1016/j.ejmech.2014.12.048Suche in Google Scholar PubMed

[7] Wang, Z.; Wang, M.; Yao, X.; Li, Y.; Tan, J.; Wang, L.; Qiao, W.; Geng, Y.; Liu, Y.; Wang, Q. Design, synthesis and antiviral activity of novel quinazolinones. Eur. J. Med. Chem.2012, 53, 275–282.10.1016/j.ejmech.2012.04.010Suche in Google Scholar PubMed

[8] Tiwari, S.; Mujalda, V.; Sharma, V.; Saxena, P.; Shrivastava, M. Synthesis and evaluation of schiff’s base of 4-quinazolinone analogues as antimicrobial agents. Asian J. Pharmaceut. Clin. Res.2012, 5, 98–100.Suche in Google Scholar

[9] Ramamohan, M.; Raghavendrarao, K.; Sridhar, R.; Nagaraju, G.; Chandrasekhar, K. B.; Jayapraksh, S. A concise approach to substituted quinazolin-4(3H)-one natural products catalyzed by iron(III) chloride. Tetrahedron Lett.2016, 57, 1418–1420.10.1016/j.tetlet.2016.02.030Suche in Google Scholar

[10] Ma, C.; Li, Y.; Niu, S.; Zhang, H.; Liu, X.; Che, Y. N-Hydroxypyridones, phenylhydrazones, and a quinazolinone from isaria farinosa. J. Nat. Prod.2011, 74, 32–37.10.1021/np100568wSuche in Google Scholar PubMed

[11] Zhuang, Y.; Teng, X.; Wang, Y.; Liu, P.; Li, G.; Zhu, W. New quinazolinone alkaloids within rare amino acid residue from coral-associated fungus, aspergillus versicolor LCJ-5-4. Org. Lett.2011, 13, 1130–1133.10.1021/ol103164nSuche in Google Scholar PubMed

[12] Eguchi, S.; Suzuki, T.; Okawa, T.; Matsushita, Y.; Yashima, E.; Okamoto, Y. Synthesis of optically active vasicinone based on intramolecular Aza-Wittig reaction and asymmetric oxidation1. J. Org. Chem.1996, 61, 7316–7319.10.1021/jo9609283Suche in Google Scholar PubMed

[13] Bergman, J.; Brynolf, A. Synthesis of Chrysogine, a metabolite of Penicillium chrysogenum and some related 2-substituted 4-(3H)-quinazolinones. Tetrahedron1990, 46, 1295–1310.10.1016/S0040-4020(01)86694-1Suche in Google Scholar

[14] Johne, S.; Quinazoline Alkaloids. In Supplements to the 2nd Edition of Rodd’s Chemistry of Carbon Compounds. Elsevier Inc.: St. Louis, MO, USA, 2009; Vol. 4, pp 223–240.10.1016/B978-044453346-3.50185-2Suche in Google Scholar

[15] Kacker, I. K.; Zaheer, S. H. Potential analgesics. Part I. Synthesis of substituted 4-quinazolones. J. Indian Chem. Soc.1951, 28, 253–260.Suche in Google Scholar

[16] Kobayashi, S.; Ueno, M.; Suzuki, R.; Ishitani, H.; Kim, H. S.; Wataya, Y. Catalytic asymmetric synthesis of antimalarial alkaloids febrifugine and isofebrifugine and their biological activity. J. Org. Chem.1999, 64, 6833–6841.10.1021/jo990877kSuche in Google Scholar PubMed

[17] Takaya, Y.; Tasaka, H.; Chiba, T.; Uwai, K.; Tanitsu, M. A.; Kim, H. S.; Wataya, Y.; Miura, M.; Takeshita, M.; Oshima, Y. New type of febrifugine analogues, bearing a quinolizidine moiety, show potent antimalarial activity against Plasmodium malaria parasite. J. Med. Chem.1999, 42, 3163–3166.10.1021/jm990131eSuche in Google Scholar PubMed

[18] Mirza, B. An efficient metal-free synthesis of 2-amino-substituted-4(3H)-quinazolinones. Tetrahedron Lett.2016, 57, 146–147.10.1016/j.tetlet.2015.11.085Suche in Google Scholar

[19] Yan, B. R.; Lv, X. Y.; Du, H.; Gao, M. N.; Huang, J.; Bao, X. P. Synthesis and biological activities of novel quinazolinone derivatives containing a 1,2,4-triazolylthioether moiety. Chem. Pap.2016, 70, 983–993.10.1515/chempap-2016-0034Suche in Google Scholar

[20] Zhu, X.; Kang, S. R.; Xia, L.; Lee, J.; Basavegowda, N.; Lee, Y. R. Efficient Cu(OTf)2-catalyzed synthesis of novel and diverse 2,3-dihydroquinazolin-4(1H)-ones. Mol. Divers.2015, 19, 67–75.10.1007/s11030-014-9557-zSuche in Google Scholar PubMed

[21] Saad, S. M.; Saleem, M.; Perveen, S.; Alam, M. T.; Khan, K. M.; Choudhary, M. I. Synthesis and biological potential assessment of 2-substituted quinazolin-4(3H)-ones as inhibitors of phosphodiesterase-I and carbonic anhydrase-II. Med. Chem. (Shāriqah (United Arab Emirates))2015, 11, 336–341.10.2174/1573406410666141203123926Suche in Google Scholar PubMed

[22] Shen, G.; Zhou, H.; Sui, Y.; Liu, Q.; Zou, K. FeCl₃-catalyzed tandem condensation/intramolecular nucleophilic addition/ C–C bond cleavage: a concise synthesis of 2-substitued quinazolinones from 2-aminobenzamides and 1,3-diketones in aqueous media. Tetrahedron Lett.2016, 57, 587–590.10.1016/j.tetlet.2015.12.094Suche in Google Scholar

[23] Li, T.; Chen, M.; Yang, L.; Xiong, Z.; Wang, Y.; Li, F.; Chen, D. Copper-catalyzed consecutive reaction to construct quinazolin-4(3H)-ones and pyrido[2,3-d]pyrimidin-4(3H)-ones. Tetrahedron2016, 72, 868–874.10.1016/j.tet.2015.12.059Suche in Google Scholar

[24] El-Hashash, M. A.; Azab, M. E.; Morsy, J. M. One-pot synthesis of some dynamic 2-substituted benzoxazinones and their corresponding qinazolinones of anticipated biological activity. J. Heterocycl. Chem.2016, 53, 95–101.10.1002/jhet.2389Suche in Google Scholar

[25] Natte, K.; Neumann, H.; Wu, X. F. Pd/C as an efficient heterogeneous catalyst for carbonylative four-component synthesis of 4(3H)-quinazolinones. Catal. Sci. Technol.2015, 5, 4474–4480.10.1039/C5CY00907CSuche in Google Scholar

[26] Li, X.; Lin, Q.; Wang, L. One-pot solvent-free synthesis of 2,3-disubstituted 4(3H)- quinazolinones catalyzed by long-chain double SO₃H-functionalized Brønsted acidic ionic liquids under microwave irradiation. J. Iran. Chem. Soc.2015, 12, 897–901.10.1007/s13738-014-0553-0Suche in Google Scholar

[27] Mohammadi, A. A.; Taheri, S.; Amouzegar, A. Synthesis of novel 1H-Imidazol[1,2-a]Indeno[2,1-e]pyridine-6(5H)-ones derivatives via a one-pot four-component condensation reaction. J. Heterocycl. Chem.2015, 52, 1876–1879.10.1002/chin.201635135Suche in Google Scholar

[28] Mohammadi, A. A.; Taheri, S.; Askari, S.; Ahdenov, R. KAl(SO₄)₂.12H₂O (Alum): an efficient catalyst for the synthesis of novel bis[spiro(quinazoline-oxindole)] derivatives via one-pot pseudo five-component reactions. J. Heterocycl. Chem.2015, 52, 1871–1875.10.1002/jhet.2292Suche in Google Scholar

[29] Mohammadi, A. A.; Tahery, S.; Askari, S. One-pot five-component reaction for synthesis of some novel bis-dihydroquinazolinone derivatives. Arkivoc2014, (v), 310–318.10.3998/ark.5550190.p008.715Suche in Google Scholar

[30] Mohammadi, A. A.; Dabiri, M.; Qaraat, H. A regioselective three-component reaction for synthesis of novel 1′H-spiro[isoindoline-1,2′-quinazoline]-3,4′(3′H)-dione derivatives. Tetrahedron2009, 65, 3804–3808.10.1016/j.tet.2009.02.037Suche in Google Scholar

[31] Mohammadi, A. A.; Rohi, H.; Soorki, A. A. Synthesis and in vitro antibacterial activities of novel 2-aryl-3-(phenylamino)-2,3-dihydroquinazolin-4(1H)-one derivatives. J. Heterocycl. Chem.2013, 50, 1129–1133.10.1002/chin.201407193Suche in Google Scholar

[32] Dabiri, M.; Salehi, P.; Otokesh, S.; Baghbanzadeh, M.; Kozehgary, G.; Mohammadi, A. A. Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones using KAl(SO4)₂·12H₂O as a reusable catalyst in water and ethanol. Tetrahedron Lett.2005, 46, 6123–6126.10.1016/j.tetlet.2005.06.157Suche in Google Scholar

[33] Azizian, J.; Mohammadi, A. A.; Karimi, A. R.; Mohammadizadeh, M. R. KAl(SO₄)₂·12H₂O supported on silica gel as a novel heterogeneous system catalyzed biginelli reaction: one-pot synthesis of dihydropyrimidinones under solvent-free conditions. Appl. Catal., A-Gen2006, 300, 85–88.10.1016/j.apcata.2005.11.001Suche in Google Scholar

[34] Clinical and Laboratory Standards Institute. Performance Standards for Antimicrobial Disk Susceptibility Tests. Fourth Edition: Approved Standard M2-A4. Wayne, PA, USA, 1990.Suche in Google Scholar

[35] Clinical and Laboratory Standards Institute. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically. Fifth Edition: Approved Standard M7-A5. Wayne, PA, USA, 2000.Suche in Google Scholar

[36] Kornet, M. J.; Varia, T.; Beaven, W. Synthesis and anticonvulsant activity of 3-amino-4(3H)-quinazolinones. J. Heterocycl. Chem.1983, 20, 1553–1555.10.1002/jhet.5570200623Suche in Google Scholar

[37] Leiby, R. W. Synthesis of 3-amino-4(3H)-quinazolinones from N-(2-carbomethoxyphenyl)imidate esters. J. Org. Chem.1985, 50, 2926–2929.10.1021/jo00216a023Suche in Google Scholar

Received: 2016-11-6

Accepted: 2017-1-13

Published Online: 2017-3-29

Published in Print: 2017-4-1

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https://doi.org/10.1515/hc-2016-0201

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alum; antimicrobial activity; isatoic anhydride; ortho esters; quinazolin-4(3H)-one

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