1677-46-9|4-Hydroxy-1-methyl-2(1H)-quinolone| Ambeed

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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1
[ 1677-46-9 ]
[ 107-86-8 ]
[ 50333-13-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With pyridine; magnesium sulfate Reflux;
74%	In neat (no solvent) at 20 - 120℃; for 12h; Microwave irradiation; Green chemistry;	General Procedure for the Synthesis of 2H Pyrans. General procedure: The 1,3-dicarbonyl compound (1.0 mmol) and the α,β-unsaturated aldehyde (1.2 mmol) were measured into a reaction vessel, which was then sealed and placed in the Microwave reactor. Microwave irradiation was then generated at 300 W and the temperature increased from room temperatureto 120 °C. The reaction mixture was then held at this temperature for 8-20 min. After cooling to room temperature, the reaction vessel was opened. Reaction completion was monitored by TLC, and the crude product was dissolved in ethyl acetate and purified by silica gel column chromatography using hexane-ethyl acetate (9:1) as eluent to affordthe desired compounds.
64%	With water at 80℃; for 6h;

57%	With ytterbium(III) triflate In acetonitrile for 12h; Heating;
57%	With ytterbium(III) triflate In acetonitrile for 12h; Heating;
57%	With ytterbium(III) triflate In acetonitrile at 80℃; for 16h; Inert atmosphere;	N-methylflindersine (5) To a stirred solution of 4-hydroxy-1-methyl-2(1H)-quinolone (2.627 g, 15 mmol) and 3-methyl-2-butenal (2.523g, 30 mmol) in acetonitrile (30 mL), Yb(OTf)3 (0.93 g, 1.5 mmol) was added. The reaction mixture was refluxed for 16 h at 80 ºC. After completion of the reaction, the reaction mass was allowed to cool, then evaporated under reduced pressure, followed by flash column chromatography (1:4 to 3:2 v/v ethyl acetate/hexane gradient elution). The desired product (5) was isolated as a yellowish brown solid (2.06 g, 57 %). 1H NMR (500 MHz, CDCl3): δ 7.94 (dd, J = 7.7, 1.0 Hz, 1H), 7.52 (t, J = 8.2 Hz, 1H), 7.29 (m, 1H), 7.21 (t, J = 7.5 Hz, 1H), 6.75 (d, J = 9.9 Hz, 1H), 5.52 (d, J = 9.8 Hz, 1H), 3.68 (s, 3H), 1.51 (s, 6H); 13C NMR (125 MHz, CDCl3): δ 160.9, 155.1, 139.3, 130.7, 126.2, 123.0, 121.6, 117.9, 116.0, 113.9, 105.8, 78.6, 29.2, 28.1. LRMS (ESI): m/z 242 [M+H]+. HRMS (ESI): calcd for C15H15NO2Na [M+Na]+ 264. 0995, found 264. 0994
50%	With ethylenediamine diacetic acid In neat (no solvent) at 20℃; for 0.0833333h; Green chemistry;
	In pyridine Heating;
	With pyridine for 3h; Reflux;

Reference： [1]Neve, Juliette E.; Wijesekera, Hasanthi P.; Duffy, Sandra; Jenkins, Ian D.; Ripper, Justin A.; Teague, Simon J.; Campitelli, Marc; Garavelas, Agatha; Nikolakopoulos, George; Le, Phuc V.; De A. Leone, Priscila; Pham, Ngoc B.; Shelton, Philip; Fraser, Neil; Carroll, Anthony R.; Avery, Vicky M.; McCrae, Christopher; Williams, Nicola; Quinn, Ronald J. [Journal of Medicinal Chemistry, 2014, vol. 57, # 4, p. 1252 - 1275]
[2]Edayadulla, Naushad; Lee, Yong Rok [Bulletin of the Korean Chemical Society, 2013, vol. 34, # 10, p. 2963 - 2967]
[3]Location in patent: experimental part Jung, Ene Jin; Park, Byung Ho; Lee, Yong Rok [Green Chemistry, 2010, vol. 12, # 11, p. 2003 - 2011]
[4]Lee, Yong Rok; Kweon, Hyuk Il; Koh, Wha Soo; Min, Kyung Rak; Kim, Youngsoo; Lee, Seung Ho [Synthesis, 2001, # 12, p. 1851 - 1855]
[5]Wang, Xue; Lee, Yong Rok [Tetrahedron Letters, 2007, vol. 48, # 36, p. 6275 - 6280]
[6]Holla, Harish; Jenkins, Ian D.; Neve, Juliette E.; Pouwer, Rebecca H.; Pham, Ngoc; Teague, Simon J.; Quinn, Ronald J. [Tetrahedron Letters, 2012, vol. 53, # 52, p. 7101 - 7103]
[7]Riveira, Martin J.; Mischne, Mirta P. [Synthetic Communications, 2013, vol. 43, # 2, p. 208 - 220,13]
[8]Grundon, Michael F.; Ramachandran, V. N.; Sloan, Barbara M. [Tetrahedron Letters, 1981, vol. 22, # 32, p. 3105 - 3108]
[9]Hou, Ke-Qiang; Chen, Xue-Ping; Huang, Yiyou; Chan, Albert S. C.; Luo, Hai-Bin; Xiong, Xiao-Feng [Organic Letters, 2020, vol. 22, # 2, p. 584 - 588]

2
[ 1677-46-9 ]
[ 42205-38-9 ]
[ 132524-77-7 ]

Reference： [1]Pharmazie,1990,vol. 45,p. 671 - 673

3
[ 57513-54-9 ]
[ 1677-46-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium hydroxide for 3h; Heating;

Reference： [1]Coppola, Gary M.; Damon, Robert E.; Hardtmann, Goetz E. [Synthesis, 1981, # 5, p. 391 - 392]

4
[ 1677-46-9 ]
[ 68-12-2 ]
[ 32262-17-2 ]
[ 96600-76-9 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 62 - 66

5
[ 1677-46-9 ]
[ 2543-57-9 ]
[ 18150-54-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	In methanol at 100℃; 1.) 500 mmHg, 15 min, 2.) 18 mmHg, 15 min;

Reference： [1]Bravo, Pierfrancesco; Resnati, Giuseppe; Viani, Fiorenza; Cavicchio, Giancarlo [Journal of Chemical Research, Miniprint, 1986, # 10, p. 3250 - 3264]

6
[ 1677-46-9 ]
[ 142577-03-5 ]
4-(4-Isopropyl-6-methoxy-1,1,3-trioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-ylmethoxy)-1-methyl-1H-quinolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride 1.) DMF, RT, 30 min, 2.) DMF, RT, 144 h; Yield given. Multistep reaction;

Reference： [1]Hlasta, Dennis J.; Ackerman, James H.; Court, John J.; Farrell, Robert P.; Johnson, Judith A.; et al. [Journal of Medicinal Chemistry, 1995, vol. 38, # 23, p. 4687 - 4692]

7
[ 1677-46-9 ]
[ 69-78-3 ]
3-(3-carboxy-4-nitrophenylthio)-4-hydroxy-1-methyl-2(1H)-quinolone [ No CAS ]

Reference： [1]Monatshefte fur Chemie,1999,vol. 130,p. 1147 - 1157

8
[ 1677-46-9 ]
[ 119-80-2 ]
3-(2-carboxyphenylthio)-4-hydroxy-1-methyl-2(1H)-quinolone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate In N,N-dimethyl-formamide at 90 - 95℃; for 5h;

Reference： [1]Schnell, Barbara; Kappe, Thomas [Monatshefte fur Chemie, 1999, vol. 130, # 9, p. 1147 - 1157]

9
[ 13099-95-1 ]
[ 1677-46-9 ]
13-methyl-6H,12H-benzofuro[2',3';4,5]pyrano[3,2-c]quinoline-6,12-dione [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1999,vol. 38,p. 148 - 151

10
[ 50-00-0 ]
[ 99-83-2 ]
[ 1677-46-9 ]
7,7a,8,9-tetrahydro-5,9,11a-trimethyl-6H,11H-[1]benzopyrano[3,2-c]quinolin-6-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	In 1,4-dioxane for 6h; Heating;

Reference： [1]Nair, Vijay; Treesa; Jayan; Rath, Nigam P; Vairamani; Prabhakar [Tetrahedron, 2001, vol. 57, # 36, p. 7711 - 7717]

11
[ 1677-46-9 ]
[ 3132-99-8 ]
[ 1016-47-3 ]
N-(2-{2-[(3-bromo-phenyl)-(4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)-methyl]-1H-indol-3-yl}-ethyl)-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	In acetic acid at 65℃;

Reference： [1]Yamamoto, Yasuo; Kurazono, Mizuyo [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 6, p. 1626 - 1628]

12
[ 18706-63-3 ]
[ 1677-46-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 93 percent / sodium hydroxyde / ethanol; H₂O / 0.02 h / 190 °C / microwave irradiation 2: 95 percent / sulfuric acid / 0.03 h / 200 °C / microwave irradiation
	Multi-step reaction with 2 steps 1: 93 percent / NaOH / ethane-1,2-diol; H₂O / 1 h / Heating 2: 95 percent / 90percent H₂SO₄ / 0.25 h / 140 °C
	Multi-step reaction with 4 steps 1: nitric acid; sulfuric acid; acetic acid 2: sodium hydroxide / water 3: selenium(IV) oxide / 1,4-dioxane / 4 h / Reflux 4: sodium hydroxide / water / 6 h / Reflux

Reference： [1]Razzaq, Tahseen; Kappe, C. Oliver [Tetrahedron Letters, 2007, vol. 48, # 14, p. 2513 - 2517]
[2]Roschger, Peter; Stadlbauer, Wolfgang [Liebigs Annalen der Chemie, 1990, # 8, p. 821 - 823]
[3]Abass, Mohamed; Allimony, Hassan A.; Hassan, Heba [Phosphorus, Sulfur and Silicon and the Related Elements, 2013, vol. 188, # 12, p. 1799 - 1810]

13
[ 1677-46-9 ]
[ 79966-13-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 89 percent / HNO₃, H₂SO₄ / acetic acid / 48 h 2: 72 percent / POCl₃, pyridine / 2 h / 60 °C
	Multi-step reaction with 2 steps 1: 89 percent / HNO₃, H₂SO₄ / acetic acid / 48 h 2: POCl₃ / dimethylformamide / 3 h / Ambient temperature
	Multi-step reaction with 2 steps 1: 90 percent / conc. HNO₃, NaNO₂ / acetic acid / 0.5 h 2: 92 percent / triethylamine, phosphoryl chloride / 1 h / Heating

Reference： [1]Drozd, V. N.; Knyazev, V. N.; Nam, N. L.; Lezina, V. P.; Mozhaeva, T. Ya.; Savel'ev, V. L. [Russian Journal of Organic Chemistry, 1993, vol. 29, # 4.2, p. 653 - 658][Zhurnal Organicheskoi Khimii, 1993, vol. 29, # 4, p. 782 - 788]
[2]Drozd, V. N.; Knyazev, V. N.; Nam, N. L.; Lezina, V. P.; Mozhaeva, T. Ya.; Savel'ev, V. L. [Russian Journal of Organic Chemistry, 1993, vol. 29, # 4.2, p. 653 - 658][Zhurnal Organicheskoi Khimii, 1993, vol. 29, # 4, p. 782 - 788]
[3]Roschger, Peter; Fiala, Werner; Stadlbauer, Wolfgang [Journal of Heterocyclic Chemistry, 1992, vol. 29, # 1, p. 225 - 231]

14
[ 1677-46-9 ]
[ 96600-76-9 ]

Reference： [1]Journal fur Praktische Chemie - Chemiker-Zeitung,1993,vol. 335,p. 128 - 134
[2]Journal fur Praktische Chemie - Chemiker-Zeitung,1993,vol. 335,p. 128 - 134
[3]Liebigs Annalen der Chemie,1991,p. 401 - 403
[4]Liebigs Annalen der Chemie,1991,p. 401 - 403

15
[ 1677-46-9 ]
[ 2058-72-2 ]
[ 5356-71-8 ]
5'-bromo-1',5-dimethyl-8,10-diphenyl-10,11-dihydrospiro[benzo[h]pyrazolo[3,4-b][1,6]naphthyridine-7,3'-indoline]-2',6(5H)-dione [ No CAS ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 9316 - 9321

16
[ 1677-46-9 ]
[ 4230-93-7 ]
[ 1296198-95-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With N-ethyl-N,N-diisopropylamine In methanol at 20℃; for 2h; Inert atmosphere; optical yield given as %de; regioselective reaction;	4.3. General procedure for the synthesis of hydroxyiminodihydrofuroquinolinone derivatives General procedure: A mixture of 4-hydroxy-N-methylquinolin-2(1H)one (13) (1 mmol) and β-nitrostyrene (14) (1.2 mmol) dissolved in 3 mL of methanol. To this solution, 10 mol% of DIPEA was added and the reaction mixture was stirred at room temperature for the time indicated in the Table 4. The progress of the reaction was monitored by TLC. After completion of the reaction, water was added, the resulting solid product was filtered and washed with water (2×10 mL) and n-hexane (5×10 mL). Then solid was dried under a vacuum to give the product (15a-g) as a mixture of Z and E isomers of angular hydroxyiminodihydrofuroquinolinone in exellent yields (82-92%).

Reference： [1]Location in patent: experimental part Barange, Deepak Kumar; Kavala, Veerababurao; Kuo, Chun-Wei; Lei, Po-Min; Yao, Ching-Fa [Tetrahedron, 2011, vol. 67, # 16, p. 2870 - 2877]

17
[ 1677-46-9 ]
[ 91-56-5 ]
[ 109-77-3 ]
[ 497080-31-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With FeNi₃ magnetic nanoparticles supported SiO₂ In water at 20℃; for 0.25h; Green chemistry;
94%	With sodium acetate In neat (no solvent) at 20℃; for 0.25h; Milling; Green chemistry;	General procedure. General procedure: Isatin 1 (3 mmol), malononitrile (0.2 g, 3 mmol,), bicyclic CH-acid 2 (3 mmol) and sodium acetate (0.025 g, 0.3 mmol) in 'solvent-free' manner or with additive ('on-solvent' manner) were grinded with a pestle and mortar at ambient temperature for 15 minutes. After the reaction was finished, the mixture was air-dried. Then the crude solid was put on filter, rinsed with water (2 mL) and EtOH (2 mL), and then dried with a water pump to isolate the spiro-oxindole 3.
90%	With 1-butyl-3-methylimidazolium Tetrafluoroborate at 25℃; for 0.0833333h;	4.1. Typical procedure for preparation of ethyl 2'-amino-3'-cyano-6'-methyl-2-oxo-spiro[indoline-3,4'-pyran]-5'-carboxylate General procedure: A mixture of isatin 1a (0.147 g, 1 mmol), malononitrile 2a (0.066 g, 1 mmol), and ethyl aceto-acetate 3a (0.13 mL, 1 mmol) was added to a vial containing a magnetic stirring bar and the ionic liquid ([BMIm]BF4, 5 drops). The reaction mixture was sealed and stirred at room temperature until disappearance of the starting materials (under 1 min). At this stage, the product due to poor solubility in the ionic liquid appears as a precipitate. In order to extract the ionic liquid, after completion of the reaction, the residue was washed with 2×10 mL of either water or diethyl ether. Washing the solid residue with ethanol (10 mL, 95.5%) has given remarkably pure powders of product 4a. The ionic liquid was recovered from the aqueous or ethereal extracts by evaporating under reduced pressure and reused in the next cycles.

86%	With 2-amino-2-hydroxymethyl-1,3-propanediol In ethanol at 20℃; for 4h;	4.1. General procedure for the synthesis of spirooxindoles, 4,6, 8 and 10 General procedure: To a well-stirred solution of isatin and malononitrile(1 mmol each) in ethanol (95%, 4 mL) was added dimedone,4-hydroxycoumarin, 4-hydroxy-N-methylquinolin-2-one,or 2-methyl-pyrazol-2-one [generated in situ from ethylacetoacetate and hydrazine hydrate, 1 mmol each]. To thissolution was added THAM (30 mol %) and stirring wascontinued at ambient temperature. Upon completion of thereaction (TLC), water (5 mL) was added and stirring wascontinued for 10 min more. Resultant solid product wasfiltered, washed repeatedly with water, and dried. The dried solid was washed thrice with hexaneechloroformmixture (1:1, v/v) and dried again. Resultant product didnot require any further purification.
83%	With piperidine In water at 50℃; for 0.0833333h; Sonication;	Typical procedure for the preparation of (4) A tube was charged with 4-hydroxy-2H-quinolone (0.16 g, 1 mmol), isatin (0.15 g, 1 mmol), malanonitrile (0.06 g, 1 mmol), piperidine (5 mol %) and water (5 mL). The reaction mixture was sonicated at 50 C for 5 min. After completion of reaction, as monitored by TLC, the reaction mixture was cooled to room temperature, filtered and the solids were wash with water and ethanol to afford the product 4a as white powder (86 %). A library of products (4a-j , see Table 3) were efficiently synthesized by this method among them 4a-e and 4i-j are known compounds,10 but the products 4f-g are reported here for the first time.

Reference： [1]Nasseri, Mohammad Ali; Sadeghzadeh, Seyed Mohsen [Journal of the Iranian Chemical Society, 2013, vol. 10, # 5, p. 1047 - 1056]
[2]Elinson, Michail N.; Vereshchagin, Anatoly N.; Ryzhkov, Fedor V.; Anisina, Yuliya E. [Arkivoc, 2018, vol. 2018, # 4, p. 276 - 285]
[3]Location in patent: experimental part Rad-Moghadam, Kurosh; Youseftabar-Miri, Leila [Tetrahedron, 2011, vol. 67, # 31, p. 5693 - 5699]
[4]Khot, Supriya S.; Anbhule, Prashant V.; Desai, Uday V.; Wadgaonkar, Prakash P. [Comptes Rendus Chimie, 2018, vol. 21, # 9, p. 814 - 821]
[5]Gholizadeh, Shaghyegh; Radmoghadam, Koorosh [Oriental Journal of Chemistry, 2013, vol. 29, # 4, p. 1637 - 1641]

18
[ 1677-46-9 ]
[ 6552-63-2 ]
[ 1642134-13-1 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 23287 - 23291

19
[ 1677-46-9 ]
[ 644-34-8 ]
[ 1642134-14-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With 1-methyl-3-(4-sulfobutyl)-1H-imidazol-3-ium 4-methylbenzene-1-sulfonate In neat (no solvent) at 110℃; for 6h; Green chemistry; regioselective reaction;

Reference： [1]Bagdi, Avik Kumar; Hajra, Alakananda [RSC Advances, 2014, vol. 4, # 44, p. 23287 - 23291]

20
[ 1677-46-9 ]
[ 626-96-0 ]
2,7-dimethyl-2,3,4,5-tetrahydro-2,5-epoxyoxepino[3,2-c]quinolin-6(7H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With <i>L</i>-proline In 1,2-dichloro-ethane at 20℃; Inert atmosphere;

Reference： [1]Tan, Haibo; Chen, Xinzheng; Chen, Huiyu; Liu, Hongxin; Qiu, Shengxiang [European Journal of Organic Chemistry, 2015, vol. 2015, # 22, p. 4956 - 4963]

21
[ 1677-46-9 ]
[ 5438-41-5 ]
3-(benzo[d][1,3]dioxol-5-yl)-2,5-dimethylfuro[3,2-c]quinolin-4(5H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With 1,4-diaza-bicyclo[2.2.2]octane In ethanol at 85℃; for 5h; regioselective reaction;

Reference： [1]Ghosh, Monoranjan; Hajra, Alakananda [European Journal of Organic Chemistry, 2015, vol. 2015, # 35, p. 7836 - 7841]

22
[ 1677-46-9 ]
[ 4996-22-9 ]
[ 109-77-3 ]
2-amino-6-methyl-4-(4-nitrobenzoyl)-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carbonitrile [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 24464 - 24469

23
[ 1677-46-9 ]
[ 16182-15-3 ]
4-hydroxy-3-(mesitylthio)-1-methylquinolin-2(1H)-one [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 3050 - 3056

24
[ 1677-46-9 ]
[ 33008-06-9 ]
3-((5-(dimethylamino)naphthalen-1-yl)thio)-4-hydroxy-1-methylquinolin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With 1,4-diaza-bicyclo[2.2.2]octane; copper(I) bromide dimethylsulfide complex; In 1,4-dioxane; at 100℃; for 6h;	General procedure: Arylsulfanyl-4-hydroxyquinolinone derivatives and various 3-arylsulfanyl-4-hydroxycoumarin and 3-arylsulfanyl-4-hydroxyquinolinone derivatives. First, 4-hydroxy coumarin / 4-hydroxyquinolinone (1.0 mmol), arylsulfonyl hydrazide (1.5 mmol), CuBrMe2S (10 mol%) and DABCO , 4-dioxane solvent and stirred well at refluxAll. After completion of the reaction, the solvent was evaporated in vacuo, and the residue was purified by column chromatography on a mixture of ethyl acetate and hexane as eluent to give pure 3-aryl sulfamide (3a-3r) and a 3-arylsulfanyl-4-hydroxyquinolinone derivative (5a-5m) were obtained.

Reference： [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 3050 - 3056
[2]Patent: KR101893515,2018,B1 .Location in patent: Paragraph 0109; 0110; 0151; 0152

25
[ 1677-46-9 ]
[ 3735-92-0 ]
3-dimethylaminothiocarbonylthio-4-hydroxy-1-methylquinolin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 5h; Reflux;

Reference： [1]Nikam; Kappe, Thomas [Journal of Heterocyclic Chemistry, 2017, vol. 54, # 3, p. 1757 - 1762]

26
[ 31329-64-3 ]
[ 1677-46-9 ]
[ 1075-06-5 ]
3-((3,5-dimethylisoxazol-4-yl)amino)-5-methyl-2-phenylfuro[3,2-c]quinolin-4(5H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With toluene-4-sulfonic acid; In water;Reflux;	General procedure: A mixture of 3,5-disubstituted amino isoxazoles 526,25l (1.0 mmol), aryl glyoxal monohydrates 2 (1.0 mmol) and 4-hydroxy-1-methyl-2-quinolinone 3 ( 1 mmol) in water (5 mL) was refluxed for 3 h in the presence of p-TSA (5 mol %). After completion of the reaction (monitored by TLC), the mixture was cooled to room temperature and poured into ice-cold water (30 mL). The precipitate that formed was filtered off, washed with ice cold water and the crude product was purified by recrystallization from ethanol to give pure isoxazolyl amino furo[3,2-c]quinolinones 6.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 3859 - 3863

27
[ 31329-64-3 ]
[ 1677-46-9 ]
[ 80352-42-7 ]
2-(4-bromophenyl)-3-((3,5-dimethylisoxazol-4-yl)amino)-5-methylfuro[3,2-c]quinolin-4(5H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With toluene-4-sulfonic acid; In water;Reflux;	General procedure: A mixture of 3,5-disubstituted amino isoxazoles 526,25l (1.0 mmol), aryl glyoxal monohydrates 2 (1.0 mmol) and 4-hydroxy-1-methyl-2-quinolinone 3 ( 1 mmol) in water (5 mL) was refluxed for 3 h in the presence of p-TSA (5 mol %). After completion of the reaction (monitored by TLC), the mixture was cooled to room temperature and poured into ice-cold water (30 mL). The precipitate that formed was filtered off, washed with ice cold water and the crude product was purified by recrystallization from ethanol to give pure isoxazolyl amino furo[3,2-c]quinolinones 6.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 3859 - 3863

28
[ 31329-64-3 ]
[ 1677-46-9 ]
[ 1186-47-6 ]
3-((3,5-dimethylisoxazol-4-yl)amino)-2,5-dimethylfuro[3,2-c]quinolin-4(5H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With toluene-4-sulfonic acid; In water;Reflux;	General procedure: A mixture of 3,5-disubstituted amino isoxazoles 526,25l (1.0 mmol), aryl glyoxal monohydrates 2 (1.0 mmol) and 4-hydroxy-1-methyl-2-quinolinone 3 ( 1 mmol) in water (5 mL) was refluxed for 3 h in the presence of p-TSA (5 mol %). After completion of the reaction (monitored by TLC), the mixture was cooled to room temperature and poured into ice-cold water (30 mL). The precipitate that formed was filtered off, washed with ice cold water and the crude product was purified by recrystallization from ethanol to give pure isoxazolyl amino furo[3,2-c]quinolinones 6.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 3859 - 3863

29
[ 1677-46-9 ]
[ 177288-16-3 ]
C₁₂H₁₁BrN₂O [ No CAS ]
(E)-3-((5-(4-bromostyryl)-3-methylisoxazol-4-yl)amino)-2-(3-chlorophenyl)-5-methylfuro[3,2-c]quinolin-4(5H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With toluene-4-sulfonic acid; In water; for 3h;Reflux; Green chemistry;	General procedure: A mixture of 4-amino-3-methyl-5-styrylisoxazoles 127,25f (1.0 mmol, 0.750 g), aryl glyoxal monohydrates 2 (1.0 mmol, 0.502 g) and 4-hydroxy-1-methyl-2-quinolinone 3 (1 mmol, 0.656 g) in water (5 mL) was refluxed for 3 h in the presence of p-TSA (5 mol %). After completion of the reaction (monitored by TLC), the mixture was cooled to room temperature and poured into ice-cold water (30 mL). The precipitate that formed was filtered off, washed with ice cold water and the crude product was purified by recrystallization from ethanol to give pure isoxazolyl amino furo[3,2-c]quinolinones 4.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 3859 - 3863

30
[ 1677-46-9 ]
[ 6625-96-3 ]
1-methyl-3-((5-nitro-1H-indol-3-yl)methylene)quinoline-2,4(1H,3H)-dione [ No CAS ]