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CAS No. : | 1867-38-5 | MDL No. : | MFCD00126183 |
Formula : | C10H5ClN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FQSXBLOWLYPURG-UHFFFAOYSA-N |
M.W : | 188.61 | Pubchem ID : | 15847 |
Synonyms : |
|
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501 | UN#: | 2811 |
Hazard Statements: | H301-H311-H331 | Packing Group: | Ⅲ |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With triethylamine In ethanol at 50℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | at 130℃; for 1h; | |
95% | With 1-butyl-3-methylimidazolium Tetrafluoroborate at 40℃; for 3h; | |
95% | With N-benzyl-N,N,N-triethylammonium chloride at 20℃; for 0.0833333h; |
95% | In water for 0.0666667h; microwave irradiation; | |
95% | With aluminum oxide; lithium chloride In neat (no solvent) for 0.075h; Microwave irradiation; | |
95% | With aspartic Acid In ethanol; water at 20℃; for 1.5h; | General procedure for the synthesis of 2-amino-3-cyano-4H-pyrans(4a-4h), 1H-pyrano[2,3-d]pyrimidine-2,4(3H,5H)-diones(6a-6f)and1,4-dihydropyrano [2,3-c]pyrazoles (8a-8h) General procedure: A 25 mL round bottom ask was charged with aldehyde 1 (1 mmol), malononitrile 2 (1.1 mmol)andasparticacid(20 mol%)in4 mLEtOH:H2O(1:1),the reaction mixture was then stirred vigorously at room temperature for about 10 min. After that, the third reactant,dimedone3/barbituricacid5/3-methyl-1H-pyrazol-5(4H)-one7(1 mmol)was added to the reaction mixture, and stirring was continued for an appropriate time at ambient temperatureasmentionedinrespectivetablesinthetext. Oncompletion ofthe reaction (as monitored by TLC), water(5 mL) was added and stirring was continued until a solid mass precipitated out that was filtered off and washed with water to obtain a crude product.The dried crude product was successively washed by a mixture of hexane: ethyl acetate (80:20) and then dried, to obtained the desired pure product. |
95% | With triethylamine In water at 50℃; Microwave irradiation; Green chemistry; | 2.3. General procedure for the synthesis of 4 H -chromene derivatives using benzylidene-malononitrile derivatives and 5,5-dimethylcyclohexane-1,3-dione General procedure: Benzylidene malononitrile derivatives 4a-j were obtained by methodology described by Jimenez et al. [16] . In a reactional flask (25 mL) were added benzylidene- malononitrile derivatives (1.0 mmol), 5,5-dimethylcyclohexane-1,3-dione (1.0 mmol), triethylamine/H 2 O (10 mol% - 15 μL/4 mL). After the reactional flask was put in the MW reactor (55 W) for 25 min and stirred using internal magnetic stirring at 50 °C. The reactional time was monitored by TLC using mixture of hexane and ethyl ac- etate (8:2) and the plates were revealed with sublimated iodine supported on silica gel. At the end of the reaction, was effectu- ated an extraction with ethyl acetate (3 ×15 mL). The combined organic phases were concentrated by vacuum until total evapora- tion of the solvent and the product was purified by wash with heat hexane and dichloromethane (1:1). All compounds were character- ized by 1 H and 13 C NMR, FTIR and melting point ( Supplementary Material ). |
94% | With morpholine In ethanol Heating; | |
94% | With urea/choline chloride eutectic salt In water at 20℃; Green chemistry; | |
94% | With lithium perchlorate In acetonitrile at 20℃; for 2.5h; Electrolysis; | General procedure General procedure: Electrolysis was carried out at room temperature in an undivided cell using platinum electrode. The dimedone and cyano-functionalized activated alkene derivatives was taken as substrate. Experimental procedure was carried out by imposing a cathodic potential which is being recorded through potential cum galvanostat as shown in Table-1 using a twocomponent comprising dimedone (10 mmol, 1) and α-cyanocinnamonitrile derivatives (10 mmol, 2a-e) [18] in 40 mL CH3CN as solvent and 0.1 M LiClO4 as supporting electrolyte at room temperature with proper mixing by magnetic stirrer. Reaction mixture was poured into ice water to precipitate a solid and filtered off. The residue was recrystallized in ethanol to obtain a desired product (Scheme-I). This protocol has easy workup through solvent extraction. |
90% | In methanol at 20℃; for 4h; | |
89% | With mercaptoacetic acid In N,N-dimethyl-formamide at 120℃; microwave irradiation; | |
88% | With amine In N,N-dimethyl-formamide at 120℃; microwave irradiation; | |
81% | With aluminum oxide; potassium fluoride In N,N-dimethyl-formamide at 20℃; | |
80% | In ethanol for 6h; Heating; | |
70% | With triethylamine In ethanol for 0.5h; Heating; | |
With water; magnesium oxide at 20℃; for 0.25h; grinding; | ||
In ethanol at 20℃; for 0.0666667h; | General procedure for the synthesis of pyran annulated heterocycles General procedure: To a stirred mixture of aromatic aldehyde (2.0 mmol) and malononitrile (2.0 mmol) in ethanol (10 ml), a catalytic amount of DMA (5 mol%) was added at room temperature. To the precipitated solid materials, ethanolic solution of dimedone orethyl acetoacetate or barbituric acid (2.0 mmol) was added and from the resultingsolution, the products get precipitated within the time mentioned in Tables 1, 2, 3,and 4. For 4H-benzo[h]chromenes, 1-naphthol (2.0 mmol) was added to the arylidenemalononitrile and stirred at 70 C until the solid appeared. The productswere filtered, air-dried, and recrystallized from ethanol. | |
With air In ethanol at 20℃; Green chemistry; | ||
In water at 20℃; for 0.166667h; Green chemistry; | General procedure for the synthesis of compounds 5a-l General procedure: A mixture of benzaldehyde/arylglyoxal (1 mmol) and malononitrile (1 mmol) was taken in a 25 mL round bottomed flask containing water (5 mL). The suspension formed was stirred at room temperature for a suitable time given in Tables 2 and 3. Further, dimedone (2 mmol) was added and continued stirringfor a suitable time. Formed precipitate was then filtered and washed with 3 × 10 mL water and dried under vacuum to obtain pure product. Purity and structure of all the products are supported by TLC analysis, melting point determination and NMR characterization (Scheme-I). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With aspartic Acid In ethanol; water at 20℃; for 5h; | General procedure for the synthesis of 2-amino-3-cyano-4H-pyrans(4a-4h), 1H-pyrano[2,3-d]pyrimidine-2,4(3H,5H)-diones(6a-6f)and1,4-dihydropyrano [2,3-c]pyrazoles (8a-8h) General procedure: A 25 mL round bottom ask was charged with aldehyde 1 (1 mmol), malononitrile 2 (1.1 mmol)andasparticacid(20 mol%)in4 mLEtOH:H2O(1:1),the reaction mixture was then stirred vigorously at room temperature for about 10 min. After that, the third reactant,dimedone3/barbituricacid5/3-methyl-1H-pyrazol-5(4H)-one7(1 mmol)was added to the reaction mixture, and stirring was continued for an appropriate time at ambient temperatureasmentionedinrespectivetablesinthetext. Oncompletion ofthe reaction (as monitored by TLC), water(5 mL) was added and stirring was continued until a solid mass precipitated out that was filtered off and washed with water to obtain a crude product.The dried crude product was successively washed by a mixture of hexane: ethyl acetate (80:20) and then dried, to obtained the desired pure product. |
77% | With morpholine In methanol Heating; | |
With starch In water at 90℃; for 1.08333h; Green chemistry; | General procedure for the synthesis of 6-amino-1,4-dihydropyrano[2,3-c]-pyrazole-5-carbonitriles, 1-14 General procedure: A mixture of hydrazine hydrate (1.5 mmol, 80%),ethyl acetoacetate (1 mmol), aromatic aldehydes (1mmol), malononitrile (1 mmol) and starch solution(4 mL), was stirred at desired temperature for 60-90 min. Progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was cooled to RT and diluted with water. The reaction mixture was filtered for the separation of product. The crude product was purified by recrystallization from ethanol to afford pure products in excellent yield.After removal of the extra added (for work-upprocess) water from the filtered solution, the starchsolution (4 mL) is recovered and reused for thesubsequent reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With piperidine In ethanol for 0.5h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With piperidine In ethanol for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With piperidine for 5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With piperidine; In ethanol; for 1h;Reflux; | General procedure: To a solution of <strong>[604-44-4]4-chloro-1-naphthol</strong> (1) (0.01 mol) inabsolute ethanol (30 mL) and catalytic amount of piperidine(0.5 mL), alpha-cyanomono, di- or tri-substituted cinnamonitriles(2a-j) (0.01 mol) was added. The reaction mixturewas heated under reflux for 1 h, the obtained solid wasfiltered off, washed with MeOH and recrystallized fromethanol or ethanol/benzene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | In methanol for 7h; Heating; | |
With piperidine In methanol for 6h; Reflux; | Preparation of 4-amino-2,6-diaryl-5-cyanopyrimidines, 3a-s General procedure: An appropriate bisnitrile 2a-s and arylamidine 1a-s (Meloet al. 2002; Do Monte et al. 2016; Melo et al. 2017) inequimolar quantity (3.46 mmol) were dissolved in methanol(10 mL) and refluxed for 6h. The contents were cooled toroom temperature and solvent evaporated to give a solidmass which was crystallized and recrystallized from anappropriate solvent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With triethylamine In N,N-dimethyl-formamide for 8h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 60% 2: 30% | With piperidine In ethanol for 0.133333h; microwave irradiation; | |
1: 35% 2: 30% | With piperidine In ethanol at 20℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With sodium ethanolate In ethanol for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With piperidine In ethanol for 5h; Heating; | |
65% | With piperidine In ethanol at 130℃; for 0.25h; Microwave irradiation; | 2.3.2. General procedure for the synthesis of 2-amino-5,6-dihydro-8-methoxy-4-phenyl (or substituted phenyl)-4H-benzo [h]chromene-3-carbonitrile 2a-e General procedure: A mixture of 2-substituted arylidenemalononitriles (0.001 mol),namely; 2-Benzylidene malononitrile, 2-((furan-2-yl) methylene)malononitrile, 2-(4-chlorobenzylidene) malononitrile, 2-(3,4,5-trimethoxybenzylidene) malononitrile, or 2-(4-methoxybenzylidene) malononitrile, in ethanol (3 mL), were addedto a mixture of 6-methoxy-1-tetralone (1) (0.001 mol), and fewdrops of piperidine. The reaction mixture was subjected to microwaveirradiation at 130 C, (400W) for ~ 15 min. Completion of thereaction (was monitored by TLC). After cooling the product wasfiltered, and recrystallized from dilute ethanol to give compounds2a-e. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With ammonium acetate; acetic acid In ethanol for 5h; Heating; | |
86% | With ammonium acetate; acetic acid In ethanol for 12h; Reflux; | General Procedure to Obtain Derivatives 4-7(a-m) General procedure: A solution of tetralone (2.0 mmol) and benzylidenemalononitrile (3.08 mmol) respectives in ethanol 10 mL and acetic acid catalytic amount was refluxed for 12h. The solid formed on cooling was collected, washed with diethyl ether and recrystallized from ethanol. |
65% | With piperidine; ammonium acetate In ethanol at 130℃; for 0.25h; Microwave irradiation; | 2.3.12. General procedure for the synthesis of 2-amino-5,6-dihydro-8-methoxy-4-phenyl (or substituted phenyl) benzo [h] quinoline-3-carbonitrile 6a-e General procedure: A mixture of suitable 2-substituted arylidenemalononitriles(0.001 mol), namely; 2-Benzylidene malononitrile, 2-((furan-2-yl)methylene) malononitrile, 2-(4-chlorobenzylidene) malononitrile,2-(3,4,5-trimethoxybenzylidene) malononitrile, and/or 2-(4-methoxybenzylidene) malononitrile, in ethanol (3 mL), wereadded to a mixture of 6-methoxy-1-tetralone (1) (0.001 mol),ammonium acetate (0.002 mol), and few drops of piperidine. Thereaction mixture was subjected to microwave irradiation at 130 C,(400W) for ~ 15 min. Completion of the reaction (was monitored byTLC), after cooling the product was filtered, and recrystallized fromdilute ethanol to give compounds 6a-e. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With triethylamine In ethanol for 12h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 98 percent / 2.5 N sodium hypochlorite, 2 N sulfuric acid / acetonitrile / 0.5 h / Ambient temperature 2: 88 percent / 48percent hydrobromic acid / 3 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With bromine In ethanol; water at 40℃; for 1h; | |
87% | With bromine; sodium ethanolate In ethanol at 20℃; for 3h; | |
64% | With Pyridine hydrobromide In acetonitrile at 20℃; Electrochemical reaction; Electrolysis; | General procedure. General procedure: An undivided cell was equipped with a graphiteanode and iron cathode (5 cm2 area each) and connected to a DC regulatedpower supply. The cell was charged with the corresponding alkylidenemalononitrile1 (10 mmol), CH-acid 2 (10 mmol), PyHBr (7.5 mmol),and MeCN (20 ml). The mixture was electrolyzed using constant currentconditions (50 mA cm-2) at room temperature under magnetic stirring(TLC control, full consumption of olefin 1). The reaction solution was thenconcentrated under reduced pressure, the residue was treated with water,and the product was extracted with dichloromethane (3 × 20 ml), theextract was dried over Na2SO4 and concentrated. The residue was purifiedby crystallization from methanol to afford the desired cyclopropane 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With sodium at 20 - 25℃; for 24h; | 4.1. Synthesis of 6-alkyl-2-amino-4-aryl-4a,5,6,7,8,8a-hexahydro-8a-methoxy-4H-pyrano[3,2-c]pyridine-3-carbonitriles 3a-n (general procedure) General procedure: A mixture of equimolar amounts of the appropriate 1a,b and the corresponding 2a-h (10 mmol) in methanol (25 ml) containing sodium (0.46 g, 20 mmol) was stirred at room temperature (20-25 °C) for 24 h. The separated solid was collected, washed with water and crystallized from a suitable solvent affording 3a-n. |
72% | With sodium at 20 - 25℃; for 24h; | Synthesis of 6-alkyl-2-amino-4-aryl-4a,5,6,7,8,8a-hexahydro-8a-methoxy-4H-pyrano[3,2-c]pyridine-3-carbonitriles 17-57 (general procedure) General procedure: A mixture of equimolar amounts of the appropriate 1-4 and the corresponding 5-16 (10 mmol) in methanol (25 ml) containing sodium (0.46 g, 20 mmol) was stirred at room temperature (20-25 °C) for 24 h. The separated solid was collected, washed with water and crystallized from a suitable solvent affording 17-57. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With cis-dichlorobis(benzonitrile)palladium(II); sodium t-butanolate; <i>tert</i>-butyl alcohol; (5,7-dioxa-6-phosphadibenzo[a,c]cyclohepten-6-yl)dimethylamine In toluene at 22℃; for 24h; Inert atmosphere; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With tris(dibenzylideneacetone)dipalladium(0)-chloroform; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In tetrahydrofuran at 20℃; for 144h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With piperidine In ethanol for 1h; Reflux; | 2.1. Reaction of 4-methoxy-1-naphthol (1) with 2a,b General procedure: A solution of 4-methoxy-1-naphthol (1) (0.01 mmol) in EtOH (30 mL) was treated with α-cyano-p-chlorocinnamonitrile (2a) or ethyl α-cyano-p-chlorocinnamate (2b) (0.01 mmol) and piperidine (0.5 mL). The reaction mixture was heated until complete precipitation occurred (reaction times: 60 min for 2a; 120 min for 2b). The solid product which formed was collected by filtration and recrystallied from ethanol to give 3a,b. The physical and spectral data of compounds 3a,b are as follows: It should be added that spectra of 3a and 3b were recorded in THF in Table 1, as well as in the experimental part. |
With piperidine In ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With piperidine; In ethanol;Reflux; | General procedure: A suspension of 1 (1.42 g, 0.01 mol) in ethanol (30 mL) containing few drops of piperidine was treated with the appropriate alpha-cinnamonitrile derivatives 9a-c (0.01 mol). The reaction mixture was refluxed for 6-8 h. The excess of solvent was evaporated in vacuo then left to cool. The solid products formed was filtered off, washed, dried and crystallized from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With sodium at 25 - 30℃; for 24h; regioselective reaction; | 4.1.2. Method B General procedure: A mixture of equimolar amounts of 1a,b (10 mmol) and the corresponding ylidenemalononitrile 6a-h in the appropriate alcohol (25 ml) containing sodium (0.46 g; 20 mmol) was stirred at room temperature (25-30°C) for the proper time (TLC control). The separated solid was collected, washed with water and crystallized from n-butanol affording the corresponding 4a-r. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With sodium at 25 - 30℃; for 24h; regioselective reaction; | 4.1.2. Method B General procedure: A mixture of equimolar amounts of 1a,b (10 mmol) and the corresponding ylidenemalononitrile 6a-h in the appropriate alcohol (25 ml) containing sodium (0.46 g; 20 mmol) was stirred at room temperature (25-30°C) for the proper time (TLC control). The separated solid was collected, washed with water and crystallized from n-butanol affording the corresponding 4a-r. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With hydrazine hydrate; acetic acid; In ethanol; at 120℃; for 1.3h; | General procedure: A mixture of malononitrile(2) (0.01 mol) and aromatic aldehyde (3) (0.01 mol) in EtOH was heated for 1 h. Next, a mixture of the sodium salt of diethyloxaloacetate (0.01 mol) (1)and hydrazine hydrate (4) in AcOH was added. The solution was heatedat 120omicronC for 15-30 min. After cooling, the precipitated solid was filtered,and recrystallized from EtOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With sodium at 20 - 25℃; for 24h; | Synthesis of 6-alkyl-2-amino-4-aryl-4a,5,6,7,8,8a-hexahydro-8a-methoxy-4H-pyrano[3,2-c]pyridine-3-carbonitriles 17-57 (general procedure) General procedure: A mixture of equimolar amounts of the appropriate 1-4 and the corresponding 5-16 (10 mmol) in methanol (25 ml) containing sodium (0.46 g, 20 mmol) was stirred at room temperature (20-25 °C) for 24 h. The separated solid was collected, washed with water and crystallized from a suitable solvent affording 17-57. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With ammonium acetate In ethanol for 5h; Reflux; | 2-Amino-4-(4-chlorophenyl)-8-isopropyl-5-methyl-5,6,7,8-tetrahydro-quinoline-3-carbonitrile (5a) Buff solid (ethanol);to a solution of menthone (1.54 g, 0.01 mol) in absolute ethanol (30 mL), arylidene malononitrile 4a (1.88 g, 0.01 mol)and ammonium acetate (6.08 g, 0.08 mol) were added. The mixture was heated under reflux for 5 h. The separated solid as collected by filtration, dried and washed with ethanol. It was obtained 2.75 g of 5a (yield 81 %), buff solid; mp162-164°C; IR (KBr) vmax: 3421,3344, 2210, 1616 cm-1; 1HNMR (DMSO-d6, 300MHz,): d = 7.60-7.52 (2H, dd,J = 6.0 Hz, H-20, H-60 ), 7.44-7.29 (2H, dd, J = 6.0 Hz, H-30,H-50), 6.53 (2H, s,NH2,D2Oexchangeable), 2.95-2.90 (1H, m,H-8), 2.66-2.58 (2H, m, CH(CH3)2 isopropyl, H-5), 1.66-1.57(4H, m, H-6, H-7), 0.99 (3H, d, J = 6.6 Hz, C-5 CH3), 0.71(3H, d, J = 7.5 Hz, -CHCH3 isopropyl), 0.65 (3H, d,J = 7.2 Hz, -CHCH3 isopropyl); 13C NMR (DMSO-d6,400 MHz,): d = 164.32 (C, C-2), 156.85 (C, C-8a), 152.84 (C,C-4), 134.90 (C-Cl, C-40), 130.18 (C, C-10), 129.45 (CH, C-30,C-50), 128.96 (CH, C-20, C-60 ), 128.86 (C, C-4a), 127.14 (C,C-3), 116.48 (C,C:N), 46.91 (CH, C-8), 32.22 (CH, -CHCH3isopropyl), 29.83 (CH, C-5), 28.30 (CH2, C-6), 21.56 (CH2,C-7), 20.62 (CH3, C-5CH3), 16.55 (CH3, -CHCH3 isopropyl),16.35 (CH3, -CHCH3 isopropyl); EIMS m/z 341 [M?2]?(4.28), 339 [M]? (12.58), 297 (100); Anal. Calcd. for C20H22-ClN3 (339.86): C, 70.68;H, 6.52; N, 12.36. Found: C, 70.84; H,6.58; N, 12.45. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With ammonium acetate In neat (no solvent) at 100℃; for 3h; | General procedure 2 for the synthesis of 2-aminopyridines 4a-f General procedure: a mixture ofarylethylidenemalononitriles 2a-c (10 mmol), substituted acetophenones 3a-d (10 mmol), and ammonium acetate (10 mmol) (or ammonium carbonate10 mmol) was heated at 100 C for 3 h. After cooling, the reaction mixture waspoured into ice-water (20 mL) to give solid precipitate which was filtered offand recrystallized from absolute ethanol to obtain the compounds 4a-f aswhite solids |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With methanol; stannous octoate In acetonitrile at 100℃; for 0.333333h; Inert atmosphere; Microwave irradiation; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With bromine; sodium ethanolate In ethanol at 20℃; for 2h; stereoselective reaction; | (12) 4-Oxo-2,7-diaryl-5-oxa-6-azaspiro[2.4]hept-6-ene-1,1-dicarbonitriles3a-j; General Procedure General procedure: To a 15 mL EtOH suspension of benzylidenemalononitrile 1 (4mmol) and 3-aryl-2-isoxazol-5(4H)-one 2 (4 mmol) in a 50 mLbeaker, sodium ethylate (4.8 mmol) in alcohol (5 mL) waspoured. Then bromine (4 mmol) was added without cooling.The mixture was magnetically stirred at room temperature for 2h. Then reaction mixture was cooled to -10 °C for 2 h, filteredout, and dried under reduced pressure to give pure 3.(2R*,3R*)-4-Oxo-2,7-diphenyl-5-oxa-6-azaspiro[2.4]hept-6-ene-1,1-dicarbonitrile (3a)White solid; yield 0.90 g (72%); mp 188-190 °C. IR (KBr): 3052,2324, 2248, 1804, 1448, 1132, 872, 764, 700, 612 cm-1. 1H NMR(300.1 MHz, DMSO-d6): δ = 5.00 (s, 1 H, CH), 7.40-7.47 (m, 3 H,Ph), 7.50-7.66 (m, 5 H, Ph), 7.69-7.75 (m, 2 H, Ph). 13C NMR(75.5 MHz, DMSO-d6): δ = 22.4, 40.6, 44.2, 109.1, 110.7, 125.8,126.5, 128.4 (2 C), 128.8 (2 C), 129.0 (2 C), 129.1 (2 C), 130.0,131.6, 163.1, 168.4. MS (EI, 70 eV): m/z (%) = 313 (3) [M+], 268(11), 191 (10), 179 (54), 166 (60), 139 (44), 129 (75), 103 (18),77 (100), 51 (87). Anal. Calcd for C19H11N3O2: C, 72.84; H, 3.54;N, 13.41. Found: C, 72.78; H, 3.64; N, 13.46. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydrogencarbonate; In acetone; at 20℃; for 0.5h; | General procedure: To the 25 ml of dried is sequentially added in the single-port flask 0.3980g (2.0mmol) beta, beta-dicyano-4-nitrostyrolene, 0.3916g (2.2mmol) N-bromo succinimide, 0.3280g (4.0mmol) sodium acetate, 5.0mLN, N-dimethyl formamide, stirring the mixture at room temperature, thin layer chromatography for tracking detection, 25 minutes after the reaction is complete, with 10 ml ethyl acetate quenching reaction, the reaction mixture with saturated salt water (3×10 ml), distilled water (3×10 ml) wash, organic phase after drying with anhydrous sodium sulfate, filtered to remove the desiccant, pressure reducing and recovering the solvent get the crude product, post chromatographic separation and purification of the crude product (with petroleum ether and ethyl acetate volume ratio of 3:1 of the mixed solution is the eluant), get N-[ 2,2-dicyano-1 - (4-nitrophenyl) vinyl] succinimide pure product 0.5637g, the yield is 95percent, recrystallized with absolute ethanol to get the white solid,.moles of beta, beta_ dicyano-4-fluoro instead of styrene, other steps the same as in Example 1 in Example 1, the use of beta, beta_-dicyano-4-nitrostyrene used in the like, 30 minutes the reaction was complete, to give a white solid N- [2, 2- dicyano-1- (4-fluorophenyl) ethenyl] succinimide 0.505g, 94percent yield In Examples 1 to 14, The N-bromosuccinimide used was replaced with equimolar <strong>[516-12-1]N-iodosuccinimide</strong>, The sodium acetate was replaced with equimolar KHC03, and N, N-dimethylformamide was replaced with an equal volume of acetone, and the other steps were the same as the corresponding examples. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With ammonium acetate; acetic acid In ethanol for 12h; Reflux; | General Procedure to Obtain Derivatives 4-7(a-m) General procedure: A solution of tetralone (2.0 mmol) and benzylidenemalononitrile (3.08 mmol) respectives in ethanol 10 mL and acetic acid catalytic amount was refluxed for 12h. The solid formed on cooling was collected, washed with diethyl ether and recrystallized from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In water; acetonitrile at 25 - 30℃; for 18h; | Synthesis of compounds 4a-j (General method). General procedure: Phthalazine (1) (91 mg, 0.70 mmol), 1,1-dicyanoalkene 2(0.70 mmol), and isocyanide 3 (0.70 mmol) were dissolvedin acetonitrile (1 ml). After that, distilled water(0.05-0.1 ml) was added to the reaction mixture up tovisible turbidity and stirred at 25-30°C for 12-18 h. Thereaction mixture was evaporated to dryness and product 4was purified by crystallization from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86.72% | With piperidine In methanol for 6h; Reflux; | Preparation of 4-amino-2,6-diaryl-5-cyanopyrimidines, 3a-s General procedure: An appropriate bisnitrile 2a-s and arylamidine 1a-s (Meloet al. 2002; Do Monte et al. 2016; Melo et al. 2017) inequimolar quantity (3.46 mmol) were dissolved in methanol(10 mL) and refluxed for 6h. The contents were cooled toroom temperature and solvent evaporated to give a solidmass which was crystallized and recrystallized from anappropriate solvent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: piperidine / methanol / 6 h / Reflux 2: piperidine / methanol / 2 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With potassium carbonate; In isopropyl alcohol;Reflux; | General procedure: In a 100 mL flask was introduced 2-alkylthiouronium halides 1 (1 mmol) and 2-benzylidenemalononitriles derivatives 2 (1 mmol) with 1 mmol of K2CO3 in refluxed i-PrOH (10 mL). The mixture was cooled to room temperature (the progress of the reaction was monitored by TLC). Then the mixture was poured onto 100 mL of water. The obtained precipitate was filtered on Buechner and the resulting solid was recrystallized from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: 1-(2-bromophenyl)-1H-pyrrole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: 4-chlorobenzylidenemalonodinitrile In tetrahydrofuran; hexane at -78℃; for 0.25h; | Typical Procedure for the Preparation of 2-{Aryl[2-(1H-pyrrol-1-yl)phenyl]methyl}propanedinitriles (3) and 2-{Aryl[1-(1H-pyrrol-1-yl)naphthalen-2-yl]methyl}propanedinitriles (6) General procedure: 2-{Phenyl[2-(1H-pyrrol-1-yl)phenyl]methyl}propanedinitrile (3a).To a stirred solution of 1a (0.22 g, 1.0 mmol) in THF (3 mL) at -78 was added n-BuLi (1.6 M inhexane; 1.0 mmol) dropwise. After 5 min, a solution of PhCH=C(CN)2 (2a) (0.15 g, 1.0 mmol) in THF (2mL) was added and stirring was continued for an additional 15 min before addition of saturated aqueousNH4Cl (15 mL). The mixture was warmed to room temperature and extracted with AcOEt (3 10 mL).The combined extracts were washed with brine (10 mL), dried (Na2SO4), and concentrated by evaporation.The residue was purified by column chromatography on SiO2 to afford 3a (0.26 g, 88%); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.08 h / -78 °C 1.2: 0.25 h / -78 °C 2.1: hydrogen bromide / acetic acid / 0.25 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In water for 0.25h; Reflux; | Synthesis of 4,7-dihydropyrazolo[1,5-a]pyrimidines 6a-i and 7a-i (General method) General procedure: DBU (14 μl, 0.1 mmol)was added to a suspension of 2-benzylidenemalononitrile1a-i (1 mmol) and 3-aryl-1H-pyrazol-5-amine 5a,b(1 mmol) in H2O (10 ml) while stirring. The resultingmixture was refluxed until completion of the reaction (12-26 min), as confirmed by TLC. After cooling to roomtemperature, the obtained precipitate was filtered off andwashed with warm H2O (10 ml). Compounds 6e,g-i and7e,g-i were purified by column chromatography (silica gel,gradient elution from 40 to 60% EtOAc-hexane). For therest of products, further purification was not necessary |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; for 0.2h;Reflux; | General procedure: DBU (14 μl, 0.1 mmol)was added to a suspension of 2-benzylidenemalononitrile1a-i (1 mmol) and 3-aryl-1H-pyrazol-5-amine 5a,b(1 mmol) in H2O (10 ml) while stirring. The resultingmixture was refluxed until completion of the reaction (12-26 min), as confirmed by TLC. After cooling to roomtemperature, the obtained precipitate was filtered off andwashed with warm H2O (10 ml). Compounds 6e,g-i and7e,g-i were purified by column chromatography (silica gel,gradient elution from 40 to 60% EtOAc-hexane). For therest of products, further purification was not necessary |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With piperidine In ethanol for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In ethanol;Reflux; | General procedure: To a solution of quinolone derivatives 1a-e (1 mmol) in dry ethanol(30 ml), 2-(4-chlorobenzylidene) malononitrile 2 (0.188 g, 1 mmol) wasadded. The reaction mixture was heated under reflux for 1-2 h (monitoredby TLC). After reaction completion, the precipitated solid was filtered, dried, and crystallized from methanol to afford compounds 3ae |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With ammonium acetate In methanol at 65℃; diastereoselective reaction; | Synthesis of compounds 4a-o (General method) General procedure: A mixture of benzylidenemalononitrile 1a-g (3 mmol),aldehyde 2a-g (3 mmol), ester of 3-oxocarboxylic acid 3a-f(3 mmol), and NH4OAc (6 mmol) was refluxed in MeOH(10 ml). After the completion of the reaction (2-12 h), themixture was kept at -10°C for 30 min for the completeprecipitation of the product. The precipitate was collectedby filtration and dried to give pure target compounds. |
Tags: 1867-38-5 synthesis path| 1867-38-5 SDS| 1867-38-5 COA| 1867-38-5 purity| 1867-38-5 application| 1867-38-5 NMR| 1867-38-5 COA| 1867-38-5 structure
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