CN102432551A - Method for synthesizing 2-arylquinazolinethione - Google Patents
Method for synthesizing 2-arylquinazolinethione Download PDFInfo
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- CN102432551A CN102432551A CN2011103657276A CN201110365727A CN102432551A CN 102432551 A CN102432551 A CN 102432551A CN 2011103657276 A CN2011103657276 A CN 2011103657276A CN 201110365727 A CN201110365727 A CN 201110365727A CN 102432551 A CN102432551 A CN 102432551A
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- quinazolinone
- aryl
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- quinazoline ketone
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Abstract
The invention provides a method for synthesizing 2-arylquinazolinethione through vanadium catalysis. A 2-arylquinazolinethione compound is obtained by reacting o-amino aryl amide with aromatic aldehyde by a one-pot method in the presence of vanadium salt serving as a catalyst and air serving as an oxidant. The using amount of the vanadium salt serving as the catalyst is 1 (mol) percent, raw materials are readily available, cost is low, yield is high, and the process is environment-friendly and suitable for industrial production.
Description
Technical field
This patent relates to organic synthesis, organic chemical industry, medicine synthetic research field, concretely, is exactly the synthetic of 2-aryl-quinazoline ketone.
Background technology
2-aryl-quinazoline ketone compound has the good biological activity, shows pharmacologically active preferably at aspects such as antitumor, hypertension, anti-inflammatory, pain relieving, sterilizations.
2-aryl-quinazoline ketone with multiple important use has multiple compound method.
Croce etc. obtain 2 one phenyl substituted quinazoline ketone in reflux in toluene with l one aryl one 4 one dimethylin, one 2 one phenyl one 1,3 one phenodiazines, one 1,3 one divinyl and benzene isocyanic ester under nitrogen protection; Productive rate 70%-88% (Heterocycles; 1997,45,1309).One of method raw material of Croce needs multistep synthetic.
Logical HCl gas in the methanol solution of fragrant nitrile such as Connolly reacts, and obtains the imines methyl ester hydrochloride, and the latter obtains 2-aryl-quinazoline ketone with the o-amino benzoyl acid-respons again, yield 42%-70% (Synlett, 2001, (11), 1707).
Couture and co-worker thereof obtain 2-aryl-quinazoline ketone, productive rate 15%～75% (Synthesis, 1991, (11), 1609) with fragrant nitrile or fatty nitrile reaction then at the proton of highly basic LDA on-30 ℃ of amino that seize the anthranoyl DIETHANOL AMINE.
Human Ga (OTf) such as Su
3Catalysis isatoic anhydride, ammonium acetate or amine and aldehyde three components synthesizing dihydro quinazolinone in ethanol obtain 2-aryl-quinazoline ketone (Tetrahedron Letters, 2008,49,3814) with DMSO oxidation dihydroquinazoline ketone then.
More relevant with this patent is one piece of paper of Tetrahedron Letters in 2004; The method in two steps of this piece The thesis is synthesized; The first step anthranilamide and phenyl aldehyde reaction generate imine intermediate, and second step needed to use the CuCl of 3 times of molar weights of imine intermediate
2Come the oxidation imine intermediate to obtain title product 2-arylalkyl quinazolinone (Tetrahedron Letters 2004,45,3475).
These methods of front all need be passed through polystep reaction and come Synthetic 2-arylalkyl quinazolinone.Following document just can be accomplished Synthetic 2-arylalkyl quinazolinone reaction in one pot.
2010, Wang etc. with catalysis of iodine anthranilamide and phenyl aldehyde at ionic liquid [bmim
+] [BF
4 -] middle one pot reaction Synthetic 2-arylalkyl quinazolinone (Synthetic Communications, 2010,40,2633).But what this paper was not mentioned iodine from start to finish is what with measuring.With reference to the bibliographical information of some other catalysis of iodine organic reaction, general 10 (mol) % of iodine consumption or more than.In addition, though ionic liquid can be through reclaiming, removal process is cumbersome, and the ionic liquid cost high, cost an arm and a leg.
2011, Fu and co-worker thereof were with the adjacent iodine aryl carboxamides of 10% cupric bromide catalysis and benzylamine one pot reaction Synthetic 2-arylalkyl quinazolinone under air, in dimethylsulfoxide solvent.The iodo reagent of adjacent iodine virtue methane amide that this method is used and so on costs an arm and a leg, and generates hydrogen iodide in the reaction in addition, also need add acid binding agent salt of wormwood.
Summary of the invention
The new synthetic method that the purpose of this invention is to provide a kind of 2-aryl-quinazoline ketone compounds.
The present invention is oxygenant with the air, is catalyzer with the vanadic salts of 1 (mol) %, accomplishes the synthetic of 2-aryl-quinazoline ketone compounds for one pot.
The experimental implementation step of this compound method: 1mmol anthranilamide, 1mmol aromatic aldehyde, 0.01mmol catalyzer, a certain amount of solvent add in the test tube successively, at heated and stirred reaction certain hour.After the cooling, add certain water gaging, with a certain amount of ethyl acetate extraction 3 times; Organic phase is with washing twice, and the mixed solvent with sherwood oil and ETHYLE ACETATE is an eluent then, uses silica gel column chromatography separating purification; Perhaps, obtain product 2-aryl-quinazoline ketone through recrystallization in ethanol.
Embodiment
Further set forth the present invention below by embodiment, therefore do not limit the present invention among the described scope of embodiments.
Embodiment 1
1mmol anthranilamide, 1mmol phenyl aldehyde, 0.01mmol methyl ethyl diketone vanadyl, 5 milliliters of DMAC N,N solvents added in the test tube successively, 120 ℃ of stirring reactions 15 hours.After the cooling, add 10 ml waters, with 10 milliliters of ethyl acetate extractions 3 times, organic phase is with washing twice, and the mixed solvent with sherwood oil and ETHYLE ACETATE is an eluent then, obtains 2-phenylquinazoline ketone, productive rate 97% with silica gel column chromatography separating purification.
2-phenylquinazoline ketone: 1 H NMR (300 MHz, CDCl
3), δ (ppm): 11.12 (s, 1H), 8.33 (d,
J=7.52 Hz, 1H), 8.20-8.22 (m, 2H) 7.78-7.85 (m, 2H), 7.59 (t,
J=2.78 Hz, 3H) 7.51 (t,
J=3.19 Hz, 1H). IR (CHCl
3), ν (cm
-1): 2924,1730,1664,1601,1451,1375,1212,1045,942,752,694.
Embodiment 2
The experimental implementation method is with embodiment 1.Replace the methyl ethyl diketone vanadyl with vanadylic sulfate, replace DMAC N,N, obtain 2-phenylquinazoline ketone, productive rate 84% with methyl-sulphoxide.
Embodiment 3
The experimental implementation method is with embodiment 1.Replace DMAC N,N with methyl-sulphoxide, obtain 2-phenylquinazoline ketone, productive rate 96%.
Embodiment 4
The experimental implementation method is with embodiment 1.Reaction times shortened to 17 hours by 15 hours among the embodiment 1, obtained 2-phenylquinazoline ketone, productive rate 88%.
Embodiment 5
The experimental implementation method is with embodiment 1.Replace the phenyl aldehyde among the embodiment 1 with the 2-bromobenzaldehyde, obtain 2-(2-bromophenyl) quinazolinone, productive rate 99.2%.
2-(2-bromophenyl) quinazolinone: 1 H NMR (300 MHz, CDCl
3), δ (ppm): 9.54 (s, 1H), 8.32 (d,
J=7.87Hz, 1H), 7.83 (d,
J=2.23Hz, 2H), 7.71-7.77 (m, 2H), 7.48-7.57 (m, 2H), 7.41 (dt,
J=7.87Hz, 1.08Hz, 1H). IR (CHCl
3), ν (cm
-1): 3015,1673,1606,1472,1304,1216,1145,1046,945,755,666.
Embodiment 6
The experimental implementation method is with embodiment 1.Replace the phenyl aldehyde among the embodiment 1 with the 3-bromobenzaldehyde, obtain 2-(3-bromophenyl) quinazolinone, productive rate 99.2%.
2-(3-bromophenyl) quinazolinone: 1 H NMR (300 MHz, DMSO-
d 6 ), δ (ppm): 12.62 (s, 1H), 8.38 (s, 1H), 8.10-8.20 (m, 2H), 7.78-7.88 (m, 2H), 7.66-7.75 (m, 1H), 7.57-7.45 (m, 2H).
Embodiment 7
The experimental implementation method is with embodiment 1.Replace the phenyl aldehyde among the embodiment 1 with the 4-bromobenzaldehyde, obtain 2-(4-bromophenyl) quinazolinone, productive rate 54.9%.
2-(4-bromophenyl) quinazolinone: 1 H NMR (300 MHz, DMSO-
d 6 ), δ (ppm): 12.60 (s, 1H), 8.14 (t,
J=7.41Hz, 3H), 7.85 (t,
J=7.02Hz, 1H), 7.76 (t,
J=7.56Hz, 3H), 7.54 (t,
J=7.56Hz, 1H). IR (CHCl
3), ν (cm
-1): 2986,1732,1375,1216,1047,756,668.
Embodiment 8
The experimental implementation method is with embodiment 1.Replace the phenyl aldehyde among the embodiment 1 with furfural, obtain 2-furyl quinazolinone, productive rate 99.2%.
2-furyl quinazolinone: 1 H NMR (300 MHz, CDCl
3), δ (ppm): 10.85 (s, 1H), 8.30 (d,
J=7.75Hz, 1H), 7.77 (d,
J=5.36Hz, 2H), 7.66 (s, 1H), 7.45-7.50 (m, 2H), 6.65-6.67 (m, 1H). IR (CHCl
3), ν (cm
-1): 2986,1667,1603,1552,1502,1459,1344,1315,1242,1217,1173,1030,965,750,666.
Embodiment 9
The experimental implementation method is with embodiment 1.Replace the phenyl aldehyde among the embodiment 1 with paradimethy laminobenzaldehyde, obtain 2-(4-dimethylaminophenyl) quinazolinone, productive rate 74.2%.
2-(4-dimethylaminophenyl) quinazolinone: 1 H NMR (300 MHz, CDCl
3), δ (ppm): 9.83 (s, 2H), 8.27 (d,
J=7.78Hz, 1H), 8.04 (d,
J=8.92Hz, 2H), 7.85 (d,
J=8.21Hz, 1H), 7.76 (dt,
J=7.01Hz, 1.42Hz, 1H), 7.43 (t,
J=6.93Hz, 1H), 6.79 (d,
J=9.05Hz, 2H), 3.64 (s, 1H), 3.03 (s, 5H). IR (CHCl
3), ν (cm
-1): 3018,1731,1665,1592,1533,1372,1215,1046,939,750,667.
Embodiment 10
The experimental implementation method is with embodiment 1.With 3, the 5-di-tert-butyl salicylaldehyde replaces the phenyl aldehyde among the embodiment 1, obtains 2-(3,5-di-t-butyl-2-hydroxy phenyl) quinazolinone, productive rate 95.4%.
2-(3,5-di-t-butyl-2-hydroxy phenyl) quinazolinone: 1 H NMR (300 MHz, CDCl
3), δ (ppm): 14.37 (s, 1H), 10.54 (s, 1H), 8.32 (d,
J=7.95Hz, 1H), 7.74-7.83 (m, 2H), 7.47-7.59 (m, 2H) 7.26 (s, 1H), 1.49 (s, 9H), 1.39 (s, 9H). IR (CHCl
3), ν (cm
-1): 2965,1676,1610,1563,1456,1217,1047,769,667.
Embodiment 11
The experimental implementation method is with embodiment 1.Replace the phenyl aldehyde among the embodiment 1 with the 4-fluorobenzaldehyde, obtain 2-(4-fluorophenyl) quinazolinone, productive rate 95.4%.
2-(4-fluorophenyl) quinazolinone: 1 H NMR (300 MHz, DMSO-
d 6 ), δ (ppm): 12.57 (s, 1H), 8.23-8.27 (m, 2H), 8.15 (d,
J=7.92Hz, 1H), 7.84 (t,
J=6.84Hz, 1H), 7.74 (d,
J=8.08Hz, 1H), 7.53 (t,
J=7.03Hz, 1H), 7.39 (t,
J=8.85Hz, 2H).
Embodiment 12
The experimental implementation method is with embodiment 1.Replace the phenyl aldehyde among the embodiment 1 with the 4-chlorobenzaldehyde, obtain 2-(4-chloro-phenyl-) quinazolinone, productive rate 39.0%.
2-(4-chloro-phenyl-) quinazolinone: 1 H NMR (300 MHz, DMSO-
d 6 ), δ (ppm): 12.61 (s, 1H), 8.20 (d,
J=8.55Hz, 2H), 8.15 (d,
J=7.92Hz, 1H), 7.85 (t,
J=7.10Hz, 1H), 7.74 (d,
J=8.16Hz, 1H), 7.63 (d,
J=8.55Hz, 2H), 7.53 (t,
J=7.37Hz, 1H).
Embodiment 13
The experimental implementation method is with embodiment 1.Replace the phenyl aldehyde among the embodiment 1 with the 4-tolyl aldehyde, obtain 2-(4-tolyl) quinazolinone, productive rate 95.0%.
2-(4-tolyl) quinazolinone: 1 H NMR (300 MHz, DMSO-
d 6 ), δ (ppm): 12.46 (s, 1H), 8.14 (d,
J=7.95Hz, 1H), 8.09 (d,
J=8.21Hz, 2H), 7.83 (t,
J=6.87Hz, 1H), 7.72 (d,
J=7.68Hz, 1H), 7.51 (t,
J=7.02Hz, 1H), 7.35 (d,
J=8.07Hz, 2H), 2.50 (d,
J=1.65Hz, 3H).
Embodiment 14
The experimental implementation method is with embodiment 1.Replace the phenyl aldehyde among the embodiment 1 with the 3-methoxybenzaldehyde, obtain 2-(3-p-methoxy-phenyl) quinazolinone, productive rate 99.2%.
2-(3-p-methoxy-phenyl) quinazolinone: 1 H NMR (300 MHz, CDCl
3), δ (ppm): 10.75 (s, 1H), 8.31 (d,
J=8.16Hz, 1H), 7.81-7.84 (m, 2H), 7.69-7.73 (m, 2H), 7.46-7.53 (m, 2H), 7.15 (d,
J=1.71Hz, 1H), 3.95 (s, 3H). IR (CHCl
3), ν (cm
-1): 2987,1786,1679,1584,1375,1218,1043,758,669.
Claims (2)
1. the compound method of a 2-aryl-quinazoline ketone compounds is characterized in that under air, and in the presence of the vanadic salts catalyzer, adjacent amino fragrant acid amides and aromatic aldehyde reaction generate 2-aryl-quinazoline ketone compounds.
2. the compound method of a kind of 2-aryl-quinazoline ketone compounds according to claim 1 is characterized in that said vanadic salts catalyzer is methyl ethyl diketone vanadyl, vanadylic sulfate; Adjacent amino fragrant acid amides: aromatic aldehyde: the ratio of vanadic salts catalyzer is 1 ﹕, 0.8～1.5 ﹕ 0.01; Be reflected under rare gas element argon gas or the nitrogen protection and carry out, temperature is 80～160 ℃, and the reaction times is 2～24 hours.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102898385A (en) * | 2012-09-26 | 2013-01-30 | 成都理工大学 | Synthesis of 4(3H)-quinazolone through catalysis of recyclable copper oxide |
| CN102911126A (en) * | 2012-11-20 | 2013-02-06 | 成都理工大学 | Synthesis of 2-aryl quinazolone from benzyl halide and 2-amobenzamide |
| CN103275016A (en) * | 2013-06-04 | 2013-09-04 | 温州医学院附属第二医院 | Synthetic method of 2-subsituted quinazoline compounds |
| CN103408502A (en) * | 2013-07-16 | 2013-11-27 | 湖南大学 | Synthetic method of quinazolinone compounds |
| CN103588714A (en) * | 2013-11-29 | 2014-02-19 | 成都理工大学 | Potassium hydroxide promoted 2-aryl quinazolone quinazolinone synthesis method |
| CN103613550A (en) * | 2013-11-29 | 2014-03-05 | 成都理工大学 | Environment-friendly synthesis method for 4(3H)-quinazolinone |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101429165A (en) * | 2007-11-09 | 2009-05-13 | 温州大学 | Synthesis of quinazoline ketone compounds |
-
2011
- 2011-11-18 CN CN2011103657276A patent/CN102432551A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101429165A (en) * | 2007-11-09 | 2009-05-13 | 温州大学 | Synthesis of quinazoline ketone compounds |
Non-Patent Citations (7)
| Title |
|---|
| 《Mol Divers》 20100731 Atul Kumar et al. Diversity-oriented synthesis of benzimidazole, benzoxazole,benzothiazole and quinazolin-4(3H)-one libraries via potassium persulfate-CuSO4-mediated oxidative coupling reactionsof aldehydes in aqueous micelles 第331-341页 1-2 第14卷, * |
| 《石油化工高等学校学报》 20110630 王敏 等 2-取代-2,3-二氢-4（1H）-喹唑啉酮衍生物合成方法 第13-16、21页 1 第24卷, 第3期 * |
| ATUL KUMAR ET AL.: "Diversity-oriented synthesis of benzimidazole, benzoxazole,benzothiazole and quinazolin-4(3H)-one libraries via potassium persulfate–CuSO4-mediated oxidative coupling reactionsof aldehydes in aqueous micelles", 《MOL DIVERS》, vol. 14, 31 July 2010 (2010-07-31), pages 331 - 341 * |
| GUAN-WU WANG ET AL.: "Benign and Efficient Synthesis of 2-Substituted 4(3H)-Quinazolinones Mediated by Iron(III) Chloride Hexahydrate in Refluxing Water", 《BULL. CHEM. SOC. JPN.》, vol. 79, no. 9, 5 September 2006 (2006-09-05), pages 1426 - 1430 * |
| MIN WANG ET AL.: "Eco-friendly synthesis of 2-substituted-2,3-dihydro-4(1H)-quinazolinones in water", 《CHINESE CHEMICAL LETTERS》, vol. 22, 15 January 2011 (2011-01-15), pages 427 - 430 * |
| RAID J. ABDEL-JALIL ET AL.: "A novel method for the synthesis of 4(3H)-quinazolinones", 《TETRAHEDRON LETTERS》, vol. 45, 31 December 2004 (2004-12-31), pages 3475 - 3476 * |
| 王敏 等: "2-取代-2,3-二氢-4（1H）-喹唑啉酮衍生物合成方法", 《石油化工高等学校学报》, vol. 24, no. 3, 30 June 2011 (2011-06-30) * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102898385A (en) * | 2012-09-26 | 2013-01-30 | 成都理工大学 | Synthesis of 4(3H)-quinazolone through catalysis of recyclable copper oxide |
| CN102898385B (en) * | 2012-09-26 | 2015-04-08 | 成都理工大学 | Synthesis of 4(3H)-quinazolone through catalysis of recyclable copper oxide |
| CN102911126A (en) * | 2012-11-20 | 2013-02-06 | 成都理工大学 | Synthesis of 2-aryl quinazolone from benzyl halide and 2-amobenzamide |
| CN103275016A (en) * | 2013-06-04 | 2013-09-04 | 温州医学院附属第二医院 | Synthetic method of 2-subsituted quinazoline compounds |
| CN103275016B (en) * | 2013-06-04 | 2015-03-11 | 温州医科大学附属第二医院 | Synthetic method of 2-subsituted quinazoline compounds |
| CN103408502A (en) * | 2013-07-16 | 2013-11-27 | 湖南大学 | Synthetic method of quinazolinone compounds |
| CN103408502B (en) * | 2013-07-16 | 2015-07-22 | 湖南大学 | Synthetic method of quinazolinone compounds |
| CN103588714A (en) * | 2013-11-29 | 2014-02-19 | 成都理工大学 | Potassium hydroxide promoted 2-aryl quinazolone quinazolinone synthesis method |
| CN103613550A (en) * | 2013-11-29 | 2014-03-05 | 成都理工大学 | Environment-friendly synthesis method for 4(3H)-quinazolinone |
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Application publication date: 20120502 |