52851-41-9|Quinoline-2,4(1H,3H)-dione| Ambeed

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Quality Control of [ 52851-41-9 ] Purity: 97% SDS Specification

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Product Details of [ 52851-41-9 ]

CAS No. :	52851-41-9
Formula :	C₉H₇NO₂
M.W :	161.16
SMILES Code :	O=C(C1)NC2=C(C=CC=C2)C1=O
MDL No. :	MFCD02937587
InChI Key :	YZMVLKJJJCMVGX-UHFFFAOYSA-N
Pubchem ID :	3677260

Safety of [ 52851-41-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 52851-41-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.11
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	46.96
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	46.17 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.19
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.78
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.64
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.49
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.78
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.97

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.7
Solubility	3.21 mg/ml ; 0.0199 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.33
Solubility	7.53 mg/ml ; 0.0468 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.04
Solubility	0.145 mg/ml ; 0.000902 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.73 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.43

Application In Synthesis of [ 52851-41-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 52851-41-9 ]

[ 52851-41-9 ] Synthesis Path-Downstream 1~35

1
[ 52851-41-9 ]
[ 107-86-8 ]
[ 523-64-8 ]

References: [1]Tetrahedron Letters,1975,p. 3407 - 3410.

2
[ 52851-41-9 ]
[ 3558-68-7 ]
[ 59732-59-1 ]

References: [1]Chemische Berichte,1976,vol. 109,p. 1549 - 1559.

3
[ 52851-41-9 ]
[ 36412-06-3 ]

References: [1]Pharmazie,1991,vol. 46,p. 743 - 744.

5
[ 52851-41-9 ]
[ 33099-01-3 ]
N-methyl-N-(3-methyl-2,5-dioxo-4-phenyl-3,4,5,6-tetrahydro-2H-pyrano[3,2-c]quinolin-3-yl)-benzamide [ No CAS ]

References: [1]Chemical Communications,2003,p. 1868 - 1869.

6
[ 6940-78-9 ]
[ 52851-41-9 ]
2-(4-chloro-butoxy)-3H-quinolin-4-one [ No CAS ]
1-(4-chloro-butyl)-1H-quinoline-2,4-dione [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 658 - 662.

7
[ 52851-41-9 ]
1-{4-[4-(2-tert-butyl-6-trifluoromethyl-pyrimidin-4-yl)-piperazin-1-yl]-butyl}-1H-quinolin-2,4-dione [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 658 - 662.

8
[ 52851-41-9 ]
[ 34837-67-7 ]

References: [1]Pharmazie,1991,vol. 46,p. 743 - 744.

9
[ 52851-41-9 ]
[ 75-03-6 ]
[ 20886-13-9 ]

Yield	Reaction Conditions	Operation in experiment
	In ISOPROPYLAMIDE; water; mineral oil;	Step A: Preparation of 4-ethoxyquinolin-2(1H)-one. To a suspension of 6 g. of <strong>[52851-41-9]quinoline-2,4-dione</strong> in 50 ml. of dimethylacetamide is added 1.6 g. of sodium hydride (56% in mineral oil, pentane washed). The mixture is then stirred at room temperature for 90 minutes and 6 g. of ethyliodide is added and the resulting mixture is heated briefly at 35 C. followed by stirring at ambient temperature for 18 hours. The precipitate which forms is recovered by filtering and the filtrate is poured into 200 ml. of water and the resulting precipitate also recovered by filtering and dried. The two filter cakes above obtained are combined and crystallized from methanol to obtain 4-ethoxyquinolin-2(1H)-one, m.p. 223-226 C.

References: [1]Patent: US4190659,1980,A .

10
[ 52851-41-9 ]
[ 106-40-1 ]
[ 958447-20-6 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2008,vol. 47,p. 1759 - 1761.

11
[ 52851-41-9 ]
[ 623-27-8 ]
[ 112393-89-2 ]
[ 1147093-53-5 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 1723 - 1726.

12
[ 52851-41-9 ]
[ 607-68-1 ]

References: [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 6404 - 6413.

13
[ 52119-39-8 ]
[ 52851-41-9 ]

References: [1]Organic Preparations and Procedures International,2010,vol. 42,p. 557 - 563.

14
[ 1131-18-6 ]
[ 52851-41-9 ]
[ 91-56-5 ]
[ 1309588-51-9 ]

Yield	Reaction Conditions	Operation in experiment
52%	With toluene-4-sulfonic acid; In ethanol; water; at 80.0℃;	A solution of 5-aminopyrazole 5a-c (0.1 mmol), beta-diketone 3 (0.1 mmol) and isatin 6 (0.1 mmol) in H2O/EtOH [5:1 (v/v))] and a catalytic amounts of PTSA (0.1 g) was heated at 80 C (water bath) for 6-12 h. Then, the reaction mixture was filtered hot and the resulting solid products were washed with ethanol, dried in air and recrystallized from ethanol.

References: [1]Tetrahedron Letters,2011,vol. 52,p. 2664 - 2666.

15
[ 52851-41-9 ]
[ 1380215-07-5 ]
[ 1380215-24-6 ]

Yield	Reaction Conditions	Operation in experiment
51%	In N,N-dimethyl-formamide; at 80.0℃; for 0.233333h;Microwave irradiation;	General procedure: Microwave experiment was carried out using a focused microwave reactor (CEM Discover TM). A mixture of equimolar amounts of ortho-aminonitrosopyrazole 1 (1 mmol) and beta-diketone 2 (1 mmol) in dimethylformamide (1 mL) was exposed to microwave radiation from 4 to 18 min at 80 C and 100 W of power. Then, the reaction mixture was allowed to cool to room temperature, and the resulting solid products were collected by filtration, washed with ethanol, dried in air and recrystallized from dimethylformamide.

References: [1]Tetrahedron Letters,2012,vol. 53,p. 3181 - 3187.

16
[ 52851-41-9 ]
[ 1380215-08-6 ]
[ 1380215-27-9 ]

Yield	Reaction Conditions	Operation in experiment
40%	In N,N-dimethyl-formamide; at 80.0℃; for 0.166667h;Microwave irradiation;	General procedure: Microwave experiment was carried out using a focused microwave reactor (CEM Discover TM). A mixture of equimolar amounts of ortho-aminonitrosopyrazole 1 (1 mmol) and beta-diketone 2 (1 mmol) in dimethylformamide (1 mL) was exposed to microwave radiation from 4 to 18 min at 80 C and 100 W of power. Then, the reaction mixture was allowed to cool to room temperature, and the resulting solid products were collected by filtration, washed with ethanol, dried in air and recrystallized from dimethylformamide.

References: [1]Tetrahedron Letters,2012,vol. 53,p. 3181 - 3187.

17
[ 52851-41-9 ]
[ 1186195-29-8 ]
[ 1380215-32-6 ]

Yield	Reaction Conditions	Operation in experiment
41%	In N,N-dimethyl-formamide; at 80.0℃; for 0.233333h;Microwave irradiation;	General procedure: Microwave experiment was carried out using a focused microwave reactor (CEM Discover TM). A mixture of equimolar amounts of ortho-aminonitrosopyrazole 1 (1 mmol) and beta-diketone 2 (1 mmol) in dimethylformamide (1 mL) was exposed to microwave radiation from 4 to 18 min at 80 C and 100 W of power. Then, the reaction mixture was allowed to cool to room temperature, and the resulting solid products were collected by filtration, washed with ethanol, dried in air and recrystallized from dimethylformamide.

References: [1]Tetrahedron Letters,2012,vol. 53,p. 3181 - 3187.

18
[ 52851-41-9 ]
[ 52943-85-8 ]
[ 1380215-13-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	In N,N-dimethyl-formamide; at 80.0℃; for 0.1h;Microwave irradiation;	General procedure: Microwave experiment was carried out using a focused microwave reactor (CEM Discover TM). A mixture of equimolar amounts of ortho-aminonitrosopyrazole 1 (1 mmol) and beta-diketone 2 (1 mmol) in dimethylformamide (1 mL) was exposed to microwave radiation from 4 to 18 min at 80 C and 100 W of power. Then, the reaction mixture was allowed to cool to room temperature, and the resulting solid products were collected by filtration, washed with ethanol, dried in air and recrystallized from dimethylformamide.

References: [1]Tetrahedron Letters,2012,vol. 53,p. 3181 - 3187.

19
[ 52851-41-9 ]
[ 81314-61-6 ]
[ 1380215-19-9 ]

Yield	Reaction Conditions	Operation in experiment
46%	In N,N-dimethyl-formamide; at 80.0℃; for 0.233333h;Microwave irradiation;	General procedure: Microwave experiment was carried out using a focused microwave reactor (CEM Discover TM). A mixture of equimolar amounts of ortho-aminonitrosopyrazole 1 (1 mmol) and beta-diketone 2 (1 mmol) in dimethylformamide (1 mL) was exposed to microwave radiation from 4 to 18 min at 80 C and 100 W of power. Then, the reaction mixture was allowed to cool to room temperature, and the resulting solid products were collected by filtration, washed with ethanol, dried in air and recrystallized from dimethylformamide.

References: [1]Tetrahedron Letters,2012,vol. 53,p. 3181 - 3187.

20
[ 52851-41-9 ]
[ 52147-97-4 ]
[ 90-02-8 ]
rac-(6bR,14S,14aR)-14-phenyl-14,14a-dihydro-6bH-benzo[5',6'][1,2]oxathiino [4',3':4,5]pyrano[3,2-c]quinolin-7(8H)-one 1,1-dioxide [ No CAS ]
rac-(6aR,7S,14bR)-7-phenyl-9,14b-dihydro-6aH-benzo[5',6'][1,2]oxathiino[4',3':4,5]pyrano[2,3-b]quinolin-14(7H)-one 6,6-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%; 15%		General procedure: To a stirring solution of 2-hydroxybenzaldehyde derivative 1 (1.0 mmol), styrenesulfonyl chloride (0.20 g, 1.0 mmol), and K2CO3 (0.14 g, 1.0 mmol) in H2O (15 mL) for 2 h was added 4-hydroxycoumarin derivative 2 (1.2 mmol) or 4-hydroxyquinolinone (0.19 g, 1.2 mmol) and EDDA (20 mmol%) and the mixture was heated at reflux for 12 h. After completion of the reaction as indicated by TLC, the mixture was cooled to room temperature and the organics were extracted using CH2Cl2 (30 mL). Evaporation of the solvent under reduced pressure followed by column chromatography on silica gel using hexane-ethyl acetate (3:1), afforded products 3 and 4.

References: [1]Tetrahedron,2013,vol. 69,p. 4979 - 4989.

21
[ 52851-41-9 ]
[ 52147-97-4 ]
[ 148-53-8 ]
rac-(6bR,14S,14aR)-3-methoxy-14-phenyl-14,14a-dihydro-6bH-benzo[5',6'][1,2]oxathiino [4',3':4,5]pyrano[3,2-c]quinolin-7(8H)-one 1,1-dioxide [ No CAS ]
rac-(6aR,7S,14bR)-4-methoxy-7-phenyl-9,14b-dihydro-6aH-benzo[5',6'][1,2]oxathiino[4',3':4,5]pyrano[2,3-b]quinolin-14(7H)-one 6,6-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%; 19%		General procedure: To a stirring solution of 2-hydroxybenzaldehyde derivative 1 (1.0 mmol), styrenesulfonyl chloride (0.20 g, 1.0 mmol), and K2CO3 (0.14 g, 1.0 mmol) in H2O (15 mL) for 2 h was added 4-hydroxycoumarin derivative 2 (1.2 mmol) or 4-hydroxyquinolinone (0.19 g, 1.2 mmol) and EDDA (20 mmol%) and the mixture was heated at reflux for 12 h. After completion of the reaction as indicated by TLC, the mixture was cooled to room temperature and the organics were extracted using CH2Cl2 (30 mL). Evaporation of the solvent under reduced pressure followed by column chromatography on silica gel using hexane-ethyl acetate (3:1), afforded products 3 and 4.

References: [1]Tetrahedron,2013,vol. 69,p. 4979 - 4989.

22
[ 52851-41-9 ]
[ 52147-97-4 ]
[ 97-51-8 ]
rac-(6bR,14S,14aR)-5-nitro-14-phenyl-14,14a-dihydro-6bH-benzo[5',6'][1,2]oxathiino [4',3':4,5]pyrano[3,2-c]quinolin-7(8H)-one 1,1-dioxide [ No CAS ]
rac-(6aR,7S,14bR)-2-nitro-7-phenyl-9,14b-dihydro-6aH-benzo[5',6'][1,2]oxathiino[4',3':4,5]pyrano[2,3-b]quinolin-14(7H)-one 6,6-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%; 23%		General procedure: To a stirring solution of 2-hydroxybenzaldehyde derivative 1 (1.0 mmol), styrenesulfonyl chloride (0.20 g, 1.0 mmol), and K2CO3 (0.14 g, 1.0 mmol) in H2O (15 mL) for 2 h was added 4-hydroxycoumarin derivative 2 (1.2 mmol) or 4-hydroxyquinolinone (0.19 g, 1.2 mmol) and EDDA (20 mmol%) and the mixture was heated at reflux for 12 h. After completion of the reaction as indicated by TLC, the mixture was cooled to room temperature and the organics were extracted using CH2Cl2 (30 mL). Evaporation of the solvent under reduced pressure followed by column chromatography on silica gel using hexane-ethyl acetate (3:1), afforded products 3 and 4.

References: [1]Tetrahedron,2013,vol. 69,p. 4979 - 4989.

23
[ 52851-41-9 ]
[ 52147-97-4 ]
[ 1761-61-1 ]
rac-(6bR,14S,14aR)-5-bromo-14-phenyl-14,14a-dihydro-6bH-benzo[5',6'][1,2]oxathiino [4',3':4,5]pyrano[3,2-c]quinolin-7(8H)-one 1,1-dioxide [ No CAS ]
rac-(6aR,7S,14bR)-2-bromo-7-phenyl-9,14b-dihydro-6aH-benzo[5',6'][1,2]oxathiino[4',3':4,5]pyrano[2,3-b]quinolin-14(7H)-one 6,6-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%; 20%		General procedure: To a stirring solution of 2-hydroxybenzaldehyde derivative 1 (1.0 mmol), styrenesulfonyl chloride (0.20 g, 1.0 mmol), and K2CO3 (0.14 g, 1.0 mmol) in H2O (15 mL) for 2 h was added 4-hydroxycoumarin derivative 2 (1.2 mmol) or 4-hydroxyquinolinone (0.19 g, 1.2 mmol) and EDDA (20 mmol%) and the mixture was heated at reflux for 12 h. After completion of the reaction as indicated by TLC, the mixture was cooled to room temperature and the organics were extracted using CH2Cl2 (30 mL). Evaporation of the solvent under reduced pressure followed by column chromatography on silica gel using hexane-ethyl acetate (3:1), afforded products 3 and 4.

References: [1]Tetrahedron,2013,vol. 69,p. 4979 - 4989.

24
[ 52851-41-9 ]
[ 58028-74-3 ]
1,2,3,3a-tetrahydro-2'H,5H-spiro[pyrrolo[1,2-a]quinoline-4,3'-quinoline]-2',4'(1'H)-dione [ No CAS ]

References: [1]Green Chemistry,2017,vol. 19,p. 5653 - 5658.

25
[ 52851-41-9 ]
[ 762-42-5 ]
dimethyl 2-(4-oxo-1,4-dihydroquinolin-3-yl)fumarate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With triethylamine; In ethanol;Reflux;	General procedure: A suspension of 1,6-disubstituted quinoline-2,4-(1H,3H)-diones 1a-d (1 mmol) and dialkyl acetylenedicarboxylates2a,b (2 mmol) in 25 mL absolute ethanol and 0.5 mL oftriethylamine, was gently refluxed for 12-18 h (the reactionwas monitored by TLC). The resulting precipitateswere filtered off, dried and recrystallized from statessolvents.

References: [1]Chemical Papers,2018,vol. 72,p. 181 - 190.

26
[ 52851-41-9 ]
[ 762-21-0 ]
[ 94192-47-9 ]

Yield	Reaction Conditions	Operation in experiment
77%	With triethylamine; In ethanol;Reflux;	General procedure: A suspension of 1,6-disubstituted quinoline-2,4-(1H,3H)-diones 1a-f (1 mmol) in 10 mL absolute ethanol wasadded to a solution of diethyl acetylenedicarboxylate (2a)(0.170 g, 1 mmol) in 15 mL absolute ethanol and 0.5 mLof triethylamine. The reaction mixture was gently refluxedfor 4-8 h, until the reactants had disappeared (monitoredby TLC). The resulting precipitates of 3a-f were filteredoff and dried. The precipitates were recrystallized fromsuitable solvents.

References: [1]Chemical Papers,2018,vol. 72,p. 181 - 190.

27
[ 52851-41-9 ]
[ 6623-89-8 ]
2-amino-5,6-dihydro-5-oxo-4-(1',3-dihydro-2'H-indol-2-on)spiro-4H-pyrano(3,2-c)quinoline-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With pyridine;Reflux;	General procedure: A 100 cm3 round-bottom flask was flame-dried, a mixtureof 1a-1f (1 mmol), 2 (1 mmol), and 20 cm3 dry pyridinewas refluxed for 8-10 h with stirring (the reaction wasfollowed by TLC analysis). After the reaction?s completion,solvent was then removed under vacuum and theresidue was separated. The solid residue undergoesrecrystallization from the stated solvents to give purecrystals of spiro-compounds 3a-3f. 20-Amino-2,50-dioxo-50,60-dihydrospiro[indoline-3,40-pyrano-[3,2-c]quinolone]-30-carbonitrile (3a, C20H12N4O3)Colorless crystals (DMF); yield 303 mg (85%), m.p.:298-300 C; NMR (DMSO-d6): see Table 1; IR (KBr):m = 3372-3207 (NH, NH2), 3099 (Ar-H), 2205 (CN),1725, 1672, 1642 (C=O), 1600, 1596 (Ar-C=N, Ar-C=C)cm-1; MS (FAB, 70 eV): m/z = 356 (M?, 100).Crystal structure data for 3a: colourless crystals,C20H12N4O32(C3H7NO), Mr = 502.53, crystal size0.16 9 0.10 9 0.08 mm, monoclinic, space group P21/c(No. 14), a = 10.8078(3) A , b = 21.4185(6) A ,c = 11.0025(3) A , b = 106.635(1), V = 2440.34(12)A 3, Z = 4, q = 1.368 Mg m-3, l(Cu-Ka) = 0.805 mm-1,F(000) = 1056, 2hmax = 144.4, 26,760 reflections, ofwhich 4805 were independent (Rint = 0.042), 351 parameters,4 restraints, R1 = 0.038 (for 4182 I[2r(I)),wR2 = 0.097 (all data), S = 1.06, largest diff. peak/-hole = 0.297/- 0.206 e A -3.

References: [1]Monatshefte fur Chemie,2018,vol. 149,p. 635 - 644.

28
[ 98-01-1 ]
[ 52851-41-9 ]
[ 109-76-2 ]
(E)-3-(2,3,4,5-tetrahydro-1H-pyrrolo[1,2-a][1,4]diazepin-1-ylidene)quinoline-2,4(1H,3H)-dione [ No CAS ]

References: [1]Journal of Organic Chemistry,2019,vol. 84,p. 1339 - 1347.

29
[ 504-29-0 ]
[ 52851-41-9 ]
[ 80352-42-7 ]
3-(2-(4-bromophenyl)imidazo[1,2-a]pyridin-3-yl)-4-hydroxyquinolin-2(1H)-one [ No CAS ]