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[ CAS No. 32618-85-2 ] {[proInfo.proName]}

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Chemical Structure| 32618-85-2
Chemical Structure| 32618-85-2
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Product Details of [ 32618-85-2 ]

CAS No. :32618-85-2 MDL No. :MFCD07437915
Formula : C8H5N3O4 Boiling Point : -
Linear Structure Formula :- InChI Key :TWJZVXRMXVNSIE-UHFFFAOYSA-N
M.W : 207.14 Pubchem ID :816982
Synonyms :

Calculated chemistry of [ 32618-85-2 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 52.41
TPSA : 112.06 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.84
Log Po/w (XLOGP3) : 1.33
Log Po/w (WLOGP) : 0.95
Log Po/w (MLOGP) : -0.48
Log Po/w (SILICOS-IT) : -1.22
Consensus Log Po/w : 0.28

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.39
Solubility : 0.845 mg/ml ; 0.00408 mol/l
Class : Soluble
Log S (Ali) : -3.28
Solubility : 0.108 mg/ml ; 0.000519 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.57
Solubility : 5.63 mg/ml ; 0.0272 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.82

Safety of [ 32618-85-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 32618-85-2 ]

* 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.

  • Upstream synthesis route of [ 32618-85-2 ]
  • Downstream synthetic route of [ 32618-85-2 ]

[ 32618-85-2 ] Synthesis Path-Upstream   1~14

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Reference: [1] Organic Process Research and Development, 2016, vol. 20, # 12, p. 2067 - 2073
[2] Organic Letters, 2009, vol. 11, # 6, p. 1193 - 1196
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YieldReaction ConditionsOperation in experiment
95% With tri-n-propylamine; trichlorophosphate In toluene at 20 - 110℃; Step B:
Preparation of 2,4-dichloro-6-nitro-quinazoline.
Phosphorus oxychloride (6.64 mL, 72.6 mmol) was added to a suspension of 6-nitro-1 H-quinazoline-2,4-dione (5.01 g, 24.2 mmol) in toluene (100 mL) and the reaction mixture was heated to 55° C. Tri-n-propylamine (12.1 mL, 63.9 mmol) was added dropwise from an addition funnel over 25 minutes.
The reaction mixture was heated to 110° C. for 6 h, stirred at room temperature for 4 d, and then pipetted into water (75 mL) and vigorously stirred for 1 h.
The two layers were filtered and separated.
The organic layer was washed with brine (30 mL), dried (MgSO4), and concentrated to yield the titled compound (3.79 g, 67percent yield, 95percent pure) after 24 h under high vacuum.
This compound did not yield MS data. 1H NMR (600 MHz, CDCl3): 9.18 (d, J=2.4 Hz, 1H), 8.75 (dd, J=9.2, 2.5 Hz, 1H), 8.18 (d, J=9.2 Hz, 1H).
63% for 6.5 h; Reflux The reaction mixture of compound 2a (0.78 g, 3.78 mmol), PCl5 (4.11 g, 19.7 mmol) and POCl3 (16 mL) was stirred at reflux for 6.5 h. The excess POCl3 was removed by evaporation. The residue was dissolved in ice water, and then the solution pH was adjusted to pH 5-6 with saturated NaHCO3. The water phase was extracted with EtOAc (60 mL .x. 5) and the organic layer was dried over anhydrous Na2SO4, concentrated to give the crude product which was purified by column chromatography on silica gel (petroleum ether/EtOAc = 40:1) to afford compound 3a as white solid (0.58 g, 63percent); mp 122-124 °C; 1H NMR (CDCl3) δ: 8.18 (d, J = 9.0 Hz, 1H), 8.76 (dd, J1 = 9.3 Hz, J2 = 2.1 Hz, 1H), 9.18 (d, J = 1.8 Hz, 1H).
63.5%
Stage #1: for 0.5 h;
Stage #2: for 6.5 h; Reflux
General procedure: 6-Nitroquinazoline-2,4 (1H, 3H) -dione (0.782 g, 3.78 mmol),Phosphorus pentachloride (4.111 g, 19.74 mmol),Add to 16 mL of phosphorus oxychloride,The reaction mixture was heated to reflux for 6.5 h and worked up as in Example 1 (b).0.585 g of a white solid was obtained in a yield of 63.5percent. 1H-Quinazolin-2,4-one (0.5 g, 3.09 mmol) and phosphorus oxychloride (4.3 mL) were added to the reaction flask. After stirring for 0.5 h, 1.6 mL of N, N-dimethylaniline was added and the mixture was refluxed Reaction about 7h. The excess phosphorus oxychloride was distilled off under reduced pressure, and the remaining phosphorus oxychloride was taken out with chloroform. The residue was dissolved in ethyl acetate, and the excess N, N-dimethylaniline was removed with cold dilute hydrochloric acid to separate the water Phase, the organic phase was adjusted with saturated sodium bicarbonate pH = 5-6, the aqueous phase was extracted with ethyl acetate, the organic phase was combined, washed sequentially with saturated aqueous sodium chloride solution, the organic phase was dried over anhydrous magnesium sulfate, Mobile phase: ethyl acetate / petroleum ether = 50/1) to give crude product 0.649g. The crude product was recrystallized from 6 mL of methanol to give 0.489 g of a yellow flocculent solid. Yield: 79.6percent.
58% at 120℃; for 4 h; Inert atmosphere A suspension of 6-nitro-1 H-quinazoline-2,4-dione (3530 mg, 17.04 mmol) and PCIs (18826.5 mg, 88.62 mmol) in POCIs (24.1 ml, 255.62 mmol) was stirred at 120 °C under N2 for 4 (0397) hours. Then reaction crude was concentrated to dryness at low pressure and purification by typical silica gel flash chromatography (cyclohexane/AcOEt from 95:5 to 80:20) afforded the pure title compound as white solid (2412 mg, yield 58 percent). Rt= 2.1 6 min; MS (ESI) m/z: 244.3 [M-H]+, [M-H]+ calculated: 244.3. 1 H NMR (400 MHz, CDC ) δ 9.18 (d, J = 2.4 Hz, 1 H), 8.75 (dd, J = 9.2, 2.5 Hz, 1 H), 8.18 (d, J = 9.2 Hz, 1 H).
13% at 110℃; for 5 h; Inert atmosphere [00414] To a solution of 6-nitroquinazoline-2,4(lH,3H)-dione (34 g, 164.14 mmol) in POCl3 (150 mL) was added dimethyl-phenyl-amine (60 g, 492.42 mmol). The mixture was stirred at 110 °C for 5 hours. The mixture was concentrated in vacuum and the remaining residue was neutralized by aq. NaHC03. The aqueous phase was extracted with EtOAc (80 mL x3). The organic phase was concentrated to dryness and the residue was purified by silica gel column chromatography (DCM: PE = 2: 1) to give 2,4-dichloro-6- nitroquinazoline (5 g, yield: 13 percent) as a yellow solid.

Reference: [1] Patent: US2010/204226, 2010, A1, . Location in patent: Page/Page column 61
[2] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 9, p. 2797 - 2807
[3] Patent: CN102250075, 2016, B, . Location in patent: Paragraph 0395; 0414; 0415
[4] Patent: WO2018/114700, 2018, A1, . Location in patent: Page/Page column 22; 53
[5] Patent: WO2015/200534, , A2, . Location in patent: Paragraph 00414[5] Patent: , 2015, , . Location in patent: Paragraph 00414
[7] Journal of the Chemical Society, 1948, p. 1759,1765
[8] Journal of the Chemical Society, 1948, p. 1759,1765
[9] Journal of Medicinal Chemistry, 1995, vol. 38, # 18, p. 3547 - 3557
[10] Patent: US6339089, 2002, B2, . Location in patent: Referential example 3
[11] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 2, p. 75 - 80
[12] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 5, p. 2755 - 2766
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Reference: [1] Patent: US2001/6969, 2001, A1,
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Reference: [1] Patent: US2001/6969, 2001, A1,
  • 5
  • [ 17420-30-3 ]
  • [ 124-38-9 ]
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YieldReaction ConditionsOperation in experiment
96% at 70℃; for 1 h; Autoclave General procedure: 2-aminobenzonitrile (1mmol), and KCC-1/IL NPs (0.0007g) were added. The autoclave was closed, purged twice with CO2 gas, pressurized with 0.8MPa of CO2 and then heated at 70°C for 60min. Then the reactor was cooled to ambient temperature, and the resulting mixture was transferred to a 50mL round bottom flask. Upon completion, the progress of the reaction was monitored by TLC when the reaction was completed, EtOH was added to the reaction mixture and the KCC-1/IL NPs were separated by distillation under vacuum. Then the solvent was removed from solution under reduced pressure and the resulting product purified by recrystallization using n-hexane/ethyl acetate.
91% With fibrous nanosilica functionalized with sodium tripolyphosphate and 3-aminopropyltriethoxysilane In neat (no solvent) at 70℃; for 0.833333 h; Autoclave; Green chemistry General procedure: 2-aminobenzonitrile (1 mmol) and KCC-1/STPP NPs (0.7 mg) were mixed together. The autoclave was closed, purged twice with CO2 gas, pressurized to 1.5 MPa of CO2, and heated at 70°C for 50 min. Then, the reactor was cooled to ambient temperature and the resulting mixture was transferred to a 50 mL round-bottom flask. During completion, the reaction progress was monitored by TLC. Following its completion, EtOH was added to the reaction mixture and the catalyst was separated by filtration. Afterwards, the solvent was removed from the solution under reduced pressure and the resulting product was purified by recrystallization using n-hexane/ethyl acetate. The products are known and their sample characterization data is presented in the Supplemental Materials.
81% With {Eu[N(SiMe3)2](μ-O:κ2-C6H5C(O)NC6H3(iPr)2)(THF)}2; 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 100℃; for 24 h; Under anhydrous, anaerobic, argon protection, 0.0999 g (7.5 × 10 -5 mol){L2Eu [N (SiMe3) 2] · THF} 2, followed by 11.2 μL (7.5 × 10 -5 mol) of DBU,Under the protection of carbon dioxide bag, add 2mL dimethyl sulfoxide,After adding 0.3107 g (1.5 x 10-3 mol) of 2-amino-5-nitrobenzonitrile,The reaction was stirred in a constant temperature bath at 100 ° C. After 24 hours,The reaction was quenched by adding 5 mL of 2 mol / L hydrochloric acid and suction filtration. The solid was washed with 3 × 5 mL of hydrochloric acid, then with toluene and ether, the residual solvent was removed and the solid was dried to give the product in a yield of 81percent
Reference: [1] Catalysis Communications, 2015, vol. 72, p. 91 - 96
[2] Catalysis Science and Technology, 2016, vol. 6, # 5, p. 1435 - 1441
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2018, vol. 193, # 8, p. 535 - 544
[4] Tetrahedron, 2002, vol. 58, # 16, p. 3155 - 3158
[5] RSC Advances, 2015, vol. 5, # 31, p. 24670 - 24674
[6] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 4, p. 1764 - 1771
[7] European Journal of Organic Chemistry, 2016, vol. 2016, # 14, p. 2555 - 2559
[8] Patent: CN105153048, 2017, B, . Location in patent: Paragraph 0120; 0121
[9] Green Chemistry, 2014, vol. 16, # 6, p. 3142 - 3148
[10] ChemCatChem, 2016, vol. 8, # 1, p. 244 - 250
[11] Heteroatom Chemistry, 2012, vol. 23, # 3, p. 276 - 280
[12] Catalysis Science and Technology, 2014, vol. 4, # 6, p. 1608 - 1614
[13] ChemSusChem, 2017, vol. 10, # 6, p. 1145 - 1151
[14] Tetrahedron Letters, 2004, vol. 45, # 38, p. 7073 - 7075
[15] Patent: WO2008/70823, 2008, A2, . Location in patent: Page/Page column 4-5; 10-11; 6/14
[16] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 1, p. 153 - 157
[17] Patent: EP1970373, 2008, A1, . Location in patent: Page/Page column 44
[18] Inorganic Chemistry, 2012, vol. 51, # 23, p. 13001 - 13008
[19] RSC Advances, 2016, vol. 6, # 112, p. 111079 - 111089
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YieldReaction ConditionsOperation in experiment
100% at 200℃; for 2 h; Inert atmosphere [00413] A mixture of 2-amino-5-nitrobenzoic acid (20 g, 109.8 mmol) and urea (33 g, 549.1 mmol) was heated at 200 °C for 2 hours. The resulting mixture was washed with water, and the resulting solid was filtered and dried to give 6-nitroquinazoline-2,4(lH,3H)-dione (26 g, quantitative) as a yellow solid.
99% at 100 - 160℃; (Step 1) (0753) A mixture of 2-amino-5-nitro-benzoic acid (30 g, 164.71 mmol) and urea (99 g, 1647.14 mmol) was stirred overnight at 160°C. The reaction mixture was cooled to 100°C, and water (300 mL) was added thereto. The resulting precipitate was washed successively with water, acetic acid (50 mL) and methanol (100 mL), and dried to give 6-nitroquinazoline-2,4(1H,3H)-dione (33.8 g, 163 mmol, 99percent) as a yellow solid. 1H-NMR (300MHz, DMSO-d6):δ7.32(1H,d,J=9.1Hz),8.45(1H,dd,J=9.1,2.6Hz),8.58(1H,d,J=2.6 Hz),11.65(2H,brs).
99% at 160℃; A mixture of 2-amino-5-nitro-benzoic acid (30 g, 164.71 mmol) and urea (99 g, 1647.14 mmol) was heated at 160°C with stirring overnight.
The mixture was cooled, water (300 mL) was added thereto, and the precipitate was collected by filtration.
The precipitate was washed with AcOH (50 mL) and MeOH (100 mL) to give 6-nitroquinazoline-2,4(1H,3H)-dione (33.8 g, 163 mmol, 99percent) as a yellow solid.
1H NMR (300 MHz, DMSO-d6): δ 7.32 (1H, d, J=9.1 Hz), 8.45(1H,dd,J=9.1,2.6 Hz), 8.58(1H,d,J=2.6 Hz), 11.65(2H,brs).
95% at 160℃; for 4 h; Microwave irradiation A mixture of 2-Amino-5-nitrobenzoic acid (3200 mg, 17.04 mmol) and urea (10338.4 mg, 170.43 mmol) was stirred for 4 hours at 1 60 °C in a CEM® microwave apparatus. The reaction crude was triturated in water (20 ml) and filtered. (0393) Resulting solid was separated by filtration and aqueous filtrate extracted twice with ethyl acetate (2 x 25 ml). Combined organic layers were dried over Na2S04, filtered, concentrated to dryness at low pressure and resulting solid mixed with the previous one obtained by filtration. Final trituration in methanol (5 ml) and filtration of combined solids afforded pure title compound (3353.7 mg, yield 95 percent). Rt = 1 .25 min; MS (ESI) m/z: 206.0 [M-H]", [M-H]" calculated: 206.0. 1H NMR (400 MHz, DMSO-c/e) δ 1 1 .72 (s, 2H), 8.59 (d, J = 2.7 Hz, 1 H), 8.45 (dd, J = 9.0, 2.7 Hz, 1 H), 7.32 (d, J = 9.0 Hz, 1 H).
94% at 150 - 200℃; Sonographic reaction Step A:
Preparation of 6-nitro-1H-quinazoline-2,4-dione.
Urea (9.89 g, 0.165 mol) and 5-nitroanthranilic acid (6.00 g, 32.9 mmol) were heated to 200° C. with vigorous stirring for 1 h.
The melt was allowed to cool to 150° C., and water (150 mL) was slowly added.
The resulting slurry was sonicated for 1 h and stirred vigorously for an additional 2 h.
It was then cooled to 0° C., and the precipitate was collected and rinsed with water to yield the titled compound (6.43 g, 94percent yield).
This material was dried in a vacuum oven and used without further purification.
This compound did not yield MS data.
80% at 150℃; for 10 h; The mixture of 2-amino-5-nitrobenzoic acid (10.0 g, 0.055 mol) and urea (32.2 g, 0.54 mol) was stirred at 150 °C for 10 h. The reaction mixture was cooled to 100 °C and then water (50 mL) was added to quench the reaction. The crude product was obtained by filtration, and then washed with water (50 mL .x. 3). After dried under vacuum condition, compound 2a was obtained as yellow solid (9.1 g, 80percent); mp >300 °C; 1H NMR (DMSO-d6) δ 7.24 (d, J = 9.0 Hz, 1H, ArH), 8.36 (dd, J1 = 9.0 Hz, J2 = 2.7 Hz, 1H, ArH), 8.55 (d, J = 2.7 Hz, 1H, ArH).
79.4% at 200℃; for 0.166667 h; Microwave irradiation The compound 2-amino-5-nitrobenzoic acid (1.5 g, 8.24 mmol) was weighed in a microwave tube and urea (2.23 g, 37.1 mmol) was added to perform microwave reaction (power: 200 W; temperature: 200 ° C.). The reaction 10min, water 30ml, filtered, the filter cake washed with water 30ml × 3, dried to give a yellow solid 9.1g, yield: 79.4percent.
72.8%
Stage #1: at 200℃; for 1 h; Inert atmosphere; Neat (no solvent)
Stage #2: With sodium hydroxide In water
Stage #3: With acetic acid In water
Example 896-Nitroquinazoline-2,4(lH,3H)-dione A mixture of 2-amino-5-nitrobenzoic acid (0.588 g, 3.23 mmol) and urea (1.164 g, 19.38 mmol) was heated at 200°C under N2 for 1 h. The mixture was cooled to room temperature and 4 M NaOH was added until pH = 14. It was acidified to pH = 5.0 via addition of AcOH. The mixture was filtered and the yellow solid was dried to give the title compound (0.49 g, 72.8percent) as a yellow solid. MS: m/z 208.1 [M+l] +.
72.8% at 200℃; for 1 h; Inert atmosphere A mixture of 2-amino-5-nitrobenzoic acid (0.588 g, 3.23 mmol) and urea (1.164 g, 19.38 mmol) was heated at 200° C. under N2 for 1 h.
The mixture was cooled to room temperature and 4 M NaOH was added until pH=14.
It was acidified to pH=5.0 via addition of AcOH.
The mixture was filtered and the yellow solid was dried to give the title compound (0.49 g, 72.8percent) as a yellow solid. MS: m/z 208.1 [M+1]+.
53% at 160℃; for 48 h; A mixture of 14 (10.0 g, 54.91 mmol) and urea (98.93 g, 1647.2mmol) was heated to 160 C for 48 h. After complete consumption of starting material, the reaction mixture was cooled to 100 C and water (10 mL) was added to the reaction mixture. The reaction mixture was filtered and washed with water; solid residue was dissolvedin 0.5 N NaOH solution. Then the reaction mixture was heated at 100 C for 40 min. The reaction mixture was cooled to0 C and 1 N HCl (aq.) was added to adjust pH = 5. Light yellow precipitatewas filtered, washed with water and dried under vacuumto give compound 15a (6.0 g, 53percent) as a light yellow solid. MS(ESI) m/z: 206.1 (MH). 1H NMR (400 MHz, DMSO-d6): d 7.31(d, 1H, J = 9.04 Hz), 8.44 (dd, 1H, J = 2.60 Hz, 8.96 Hz), 8.57 (d, 1H,J = 2.64 Hz), 11.66 (br s, 2H).

Reference: [1] Patent: WO2015/200534, , A2, . Location in patent: Paragraph 00413[1] Patent: , 2015, , . Location in patent: Paragraph 00413
[3] Patent: EP2975031, 2016, A1, . Location in patent: Paragraph 0753
[4] Patent: EP3192791, 2017, A1, . Location in patent: Paragraph 0461
[5] Patent: WO2018/114700, 2018, A1, . Location in patent: Page/Page column 22; 52-53
[6] Patent: US2010/204226, 2010, A1, . Location in patent: Page/Page column 60
[7] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 9, p. 2797 - 2807
[8] Patent: CN102250075, 2016, B, . Location in patent: Paragraph 0408-0410
[9] Patent: WO2012/130166, 2012, A1, . Location in patent: Page/Page column 51-52
[10] Patent: US2014/23642, 2014, A1, . Location in patent: Page/Page column 0429
[11] Synlett, 2013, vol. 24, # 16, p. 2102 - 2106
[12] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 3, p. 721 - 736
[13] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 2, p. 75 - 80
[14] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 677 - 683
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YieldReaction ConditionsOperation in experiment
82%
Stage #1: at 0℃; for 3 h;
Stage #2: With sodium hydroxide In water
On an ice bath, 2 g (12,3 mmol) of quinazoline-2,4(1H,3H)-dione 2, were dissolved in 19 mL of sulfuric acid. Maintaining the mixture under agitation,a solution of 0.68 mL of nitric acid (12.3 mmol) and 1.37 mL of sulfuric acid were by dropwise added during 30 minutes and left reacting for 3 hours at 0°C. After this time, the reaction mixture was poured into a beaker containing 70ml cold water. Subsequently, 70 ml of solution 9.5N of NaOH was dropwise added. The resulting precipitate was filtered at vacuum, dried and purified by chromatographic column using petroleum-ether/ethylacetate (3/7) as eluent.This gave 2.1 g (82percent yield) of a yellow product.
Reference: [1] Journal of the Chilean Chemical Society, 2013, vol. 58, # 3, p. 1817 - 1819
[2] Tetrahedron, 1997, vol. 53, # 25, p. 8457 - 8478
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Reference: [1] Organic Process Research and Development, 2016, vol. 20, # 12, p. 2067 - 2073
[2] Organic Letters, 2009, vol. 11, # 6, p. 1193 - 1196
  • 9
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Reference: [1] Heterocycles, 2012, vol. 85, # 11, p. 2745 - 2748,4
[2] Heterocycles, 2012, vol. 85, # 11, p. 2745 - 2748
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Reference: [1] Organic Letters, 2009, vol. 11, # 6, p. 1193 - 1196
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Reference: [1] Chemistry of Heterocyclic Compounds, 2006, vol. 42, # 4, p. 540 - 545
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Reference: [1] Chemistry of Heterocyclic Compounds, 2006, vol. 42, # 4, p. 540 - 545
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Reference: [1] Chemistry of Heterocyclic Compounds, 2006, vol. 42, # 4, p. 540 - 545
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Reference: [1] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 8, p. 824 - 829
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