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[ CAS No. 1826-12-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1826-12-6
Chemical Structure| 1826-12-6
Chemical Structure| 1826-12-6
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Product Details of [ 1826-12-6 ]

CAS No. :1826-12-6 MDL No. :MFCD00092820
Formula : C9H7NS Boiling Point : -
Linear Structure Formula :- InChI Key :KXCQDIWJQBSUJF-UHFFFAOYSA-N
M.W : 161.22 Pubchem ID :74581
Synonyms :

Calculated chemistry of [ 1826-12-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.55
TPSA : 41.13 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.08
Log Po/w (XLOGP3) : 2.61
Log Po/w (WLOGP) : 2.81
Log Po/w (MLOGP) : 1.58
Log Po/w (SILICOS-IT) : 3.76
Consensus Log Po/w : 2.57

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.16
Solubility : 0.112 mg/ml ; 0.000695 mol/l
Class : Soluble
Log S (Ali) : -3.12
Solubility : 0.121 mg/ml ; 0.000753 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.8
Solubility : 0.0256 mg/ml ; 0.000158 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.93

Safety of [ 1826-12-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1826-12-6 ]

* 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 [ 1826-12-6 ]

[ 1826-12-6 ] Synthesis Path-Downstream   1~89

  • 1
  • [ 1826-12-6 ]
  • [ 100-39-0 ]
  • [ 130862-65-6 ]
YieldReaction ConditionsOperation in experiment
With ethanol
  • 4
  • [ 17574-10-6 ]
  • [ 1826-12-6 ]
YieldReaction ConditionsOperation in experiment
With ethanol; mercury(II) oxide
  • 5
  • [ 60100-09-6 ]
  • [ 532-27-4 ]
  • [ 1826-12-6 ]
YieldReaction ConditionsOperation in experiment
With piperidine; tetraphosphorus decasulfide
  • 6
  • [ 288-47-1 ]
  • [ 1826-13-7 ]
  • [ 1826-11-5 ]
  • [ 1826-12-6 ]
  • 8
  • [ 6094-68-4 ]
  • [ 1826-12-6 ]
YieldReaction ConditionsOperation in experiment
With sodium thiophenolate In methanol for 1h; Heating;
  • 9
  • [ 50-00-0 ]
  • [ 70-11-1 ]
  • [ 1826-12-6 ]
YieldReaction ConditionsOperation in experiment
(i) P2S5, dioxane, (ii) /BRN= 606474/; Multistep reaction;
  • 10
  • [ 1826-11-5 ]
  • [ 1075-21-4 ]
  • [ 1826-12-6 ]
  • [ 10514-34-8 ]
  • 11
  • [ 1826-12-6 ]
  • [ 84-58-2 ]
  • [ 125509-49-1 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane for 1.5h; Heating;
  • 12
  • [ 2010-06-2 ]
  • [ 1826-12-6 ]
YieldReaction ConditionsOperation in experiment
40% With tetrahydrofuran; oxygen; nitrogen(II) oxide for 8h; Ambient temperature;
With copper(I) oxide; sulfuric acid; hypophosphorous acid; sodium nitrite 1.) 0 deg C, 2.) H2O, from -5 deg C to RT; Yield given. Multistep reaction;
Stage #1: 2-Amino-4-phenylthiazole With sulfuric acid; trifluoroacetic acid; sodium nitrite In water at -15℃; Stage #2: With phosphoric acid In water at -15 - 20℃;
  • 13
  • [ 6907-71-7 ]
  • [ 1826-12-6 ]
YieldReaction ConditionsOperation in experiment
26 % Spectr. With sulfur dioxide at 450℃;
  • 14
  • [ 107-13-1 ]
  • [ 57516-16-2 ]
  • [ 1826-12-6 ]
  • [ 4072-63-3 ]
  • (E)-3-(4-Phenyl-thiazol-2-yl)-acrylonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 12% 2: 15% 3: 15% With triethylamine In N,N-dimethyl-formamide at 100℃; for 48h; sealed tube;
  • 15
  • [ 140-88-5 ]
  • [ 57516-16-2 ]
  • [ 1826-12-6 ]
  • [ 4072-63-3 ]
  • [ 111600-96-5 ]
YieldReaction ConditionsOperation in experiment
1: 22% 2: 6% 3: 19% With triethylamine In N,N-dimethyl-formamide at 130℃; for 24h; sealed tube;
  • 16
  • [ 100-42-5 ]
  • [ 57516-16-2 ]
  • [ 1826-12-6 ]
  • [ 111600-99-8 ]
YieldReaction ConditionsOperation in experiment
1: 7% 2: 5% With triethylamine In N,N-dimethyl-formamide at 100℃; for 48h; sealed tube;
  • 17
  • [ 57516-16-2 ]
  • [ 1826-12-6 ]
  • [ 4072-63-3 ]
  • [ 111600-96-5 ]
YieldReaction ConditionsOperation in experiment
1: 19% 2: 6% 3: 22% With triethylamine; ethyl acrylate In N,N-dimethyl-formamide at 130℃; for 24h; sealed tube;
  • 18
  • [ 57516-16-2 ]
  • [ 1826-12-6 ]
  • [ 4072-63-3 ]
  • (E)-3-(4-Phenyl-thiazol-2-yl)-acrylonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 15% 2: 12% 3: 15% With triethylamine; acrylonitrile In N,N-dimethyl-formamide at 100℃; for 48h; sealed tube;
  • 19
  • [ 1826-12-6 ]
  • [ 3844-94-8 ]
  • 3-n-butyl-4-(trimethylsilyl)thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With 1,8-diazabicyclo[5.4.0]undec-7-ene at 325 - 340℃;
73 % Turnov. With 1,8-diazabicyclo[5.4.0]undec-7-ene at 330℃; for 168h;
  • 20
  • [ 1826-12-6 ]
  • [ 501-65-5 ]
  • [ 16939-13-2 ]
YieldReaction ConditionsOperation in experiment
83% With 1,8-diazabicyclo[5.4.0]undec-7-ene at 325 - 340℃;
83 % Turnov. With 1,8-diazabicyclo[5.4.0]undec-7-ene at 340℃; for 60h;
  • 21
  • [ 1826-12-6 ]
  • [ 1066-54-2 ]
  • [ 18245-17-5 ]
YieldReaction ConditionsOperation in experiment
65% With 1,8-diazabicyclo[5.4.0]undec-7-ene at 325 - 340℃;
65 % Turnov. With 1,8-diazabicyclo[5.4.0]undec-7-ene at 340℃; for 48h;
  • 22
  • [ 1826-12-6 ]
  • [ 14630-40-1 ]
  • [ 156642-32-9 ]
YieldReaction ConditionsOperation in experiment
92% With 1,8-diazabicyclo[5.4.0]undec-7-ene at 325℃; for 144h;
92 % Turnov. With 1,8-diazabicyclo[5.4.0]undec-7-ene at 325℃; for 144h;
  • 23
  • [ 1826-12-6 ]
  • [ 51336-94-8 ]
  • 2-Chloro-1-(2,4-difluoro-phenyl)-1-(4-phenyl-thiazol-2-yl)-ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium 1.) n-hexane, THF, -78 deg C, 5 min, 2.) n-hexane, THF, -78 deg C, 1 h; Multistep reaction;
  • 24
  • [ 936-46-9 ]
  • [ 1826-12-6 ]
YieldReaction ConditionsOperation in experiment
82 % Chromat. With TEA In methanol for 0.5h; Irradiation;
With TEA In cyclohexane Irradiation; other solvents, bases; photochemistry of 4-substituted isothiazoles; effect of reaction conditions; trapping of intermediate species; mechanism; sensitized irradiation;
YieldReaction ConditionsOperation in experiment
Photolyse: Produktverteilung (Tab.1);
Photochem. Umlagerung mit u. ohne Ggw. von J2 (Tab.1);
formation of isothiazole (IIa) by irradiation (contrary see Vernin et al., Bull.Soc.Chim.Fr.1971, 1103);
Rk. mit Dibenzoylperoxid in nicht saurem Milieu/110grad: 2,4-Diphenylthiazol (14,5percent), 4,5-Diphenylthiazol (49,5percent), 4-o-Tolylthiazol (25percent), 4-m-Tolylthiazol (3percent), 4-p-Tolylthiazol (8percent);
Rk.mit HNO3:Produktverteilung;
H-D-Austausch in 2- und 4-Stellung, Geschw.Konst. K;
Ass. mit TCNE;
d. Komplexbldg. mit Tetracyanethylen zu 4-Phenyl-thiazol-Tetracyanethylen-Komplex (Bldgs.-Enthalpie u. -Entropie);
d. Komplexbldg. mit Tetracyanethylen zu 4-Phenyl-thiazol-Tetracyanethylen-Komplex;
der Rk. mit Benzoylperoxid -> 4,5-Diphenylthiazol, 2,4-Diphenylthiazol;

YieldReaction ConditionsOperation in experiment
With ethanol
  • 28
  • [ 2103-88-0 ]
  • [ 7664-41-7 ]
  • [ 1826-12-6 ]
  • [ 98-86-2 ]
  • 29
  • [ 1075-21-4 ]
  • [ 1826-13-7 ]
  • [ 1826-12-6 ]
  • [ 10514-34-8 ]
  • 30
  • [ 10514-34-8 ]
  • [ 1826-11-5 ]
  • [ 1826-12-6 ]
  • 31
  • [ 284680-73-5 ]
  • [ 1826-13-7 ]
  • [ 1826-12-6 ]
  • [ 10514-34-8 ]
  • 32
  • [ 1826-12-6 ]
  • C9H6(2)HNS [ No CAS ]
  • 4-([2',6'-2H2]-phenyl)thiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With deuterium In dichloromethane Title compound not separated from byproducts;
  • 33
  • [ 1826-12-6 ]
  • [thiazole-2-2H, benzene-2,6-2H2]-4-phenylthiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Crabtree's catalyst; water-d2; deuterium In dichloromethane at 20℃; for 90h;
  • 34
  • [ 1826-12-6 ]
  • 4-([2',6'-2H2]-phenyl)thiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With silver tetrafluoroborate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; deuterium In dichloromethane at 20℃;
  • 35
  • [ 1826-12-6 ]
  • [ 24772-65-4 ]
  • C30H38N2S2(2+)*2I(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% In acetonitrile for 72h; Heating;
  • 36
  • [ 1826-12-6 ]
  • 1-(2,4-difluorophenyl)-1-(4-phenylthiazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) n-hexane, THF, -78 deg C, 5 min, 2.) n-hexane, THF, -78 deg C, 1 h 2: 1.) NaH / 1,) DMF, 2.), DMF, 60 deg C, 3 h
  • 37
  • [ 1826-12-6 ]
  • [ 60759-10-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Nitrierung 2: Raney nickel; ethanol / Hydrogenation
Multi-step reaction with 2 steps 1: Nitrierung 2: palladium/charcoal; methanol / Hydrogenation
  • 38
  • [ 1826-12-6 ]
  • 3-(3-chlorophenyl)-2,1-benzisoxazole-5-carboxaldehyde [ No CAS ]
  • 3-(3-chlorophenyl)-α-(4-phenyl-2-thiazolyl)-2,1-benzisoxazole-5-methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.5 g (84%) With n-butyllithium; ammonium chloride In tetrahydrofuran A.3.c EXAMPLE A3 c) BuLi (0.118 mol) was added dropwise at -70° C. under N2 flow to a solution of 4-phenyl-thiazole (0.097 mol) in THF (205 ml). The mixture was stirred at -70° C. for 1 hour. A solution of intermediate (13)(0.0692 mol) in THF (205 ml) was added dropwise. The mixture was stirred at -70° C. for 2 hours, brought to -30° C. over a 90-min period, poured out into NH4Cl 10% and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue (39.5 g) was purified by column chromatography over silica gel (eluent: cyclohexane/EtOAc 80/20; 20-45 μm). The pure fractions were collected and the solvent was evaporated. A part (1.5 g) of the residue (18 g, 62%) was crystallized from 2-propanone. The precipitate was filtered off and dried, yielding 1.5 g (84%) of 3-(3-chlorophenyl)-α-(4-phenyl-2-thiazolyl)-2,1-benzisoxazole-5-methanol (intermediate 14), mp. 136° C.
  • 39
  • [ 1826-12-6 ]
  • [ 29786-93-4 ]
  • [ 38571-19-6 ]
  • (+/-)-2-[3-chloro-4-[(4-chlorophenyl)-hydroxy(4-phenyl-2-thiazolyl)methyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.83 g (11%) With ammonium acetate In tetrahydrofuran; diethyl ether; water A.15.a EXAMPLE A15 a) n-Butyl lithium (0.045 mol) was added at -70° C. under N2 flow to a solution of 4-phenyl-thiazole (0.045 mol) in diethyl ether (50 ml). The mixture was stirred at -70° C. for 90 minutes. A solution of 2-[3-chloro-4-(4-chlorobenzoyl)phenyl]-1,2,4-triazine-3,5-(2H,4H)-dione (0.015 mol) in THF (10 ml) was added at -70° C. The mixture was stirred at -70° C. for 1 hour, then poured out into ice water, neutralized with HCl 3N and extracted with EtOAc. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography oversilica gel (eluent: CH2Cl2/CH3OH 98/2). The desired fraction was repurified by HPLC (eluent: CH3OH/(NH4OAc 1% in H2O) 80/20). The pure fractions were collected and the solvent was evaporated, yielding 0.83 g (11%) of (+-)-2-[3-chloro-4-[(4-chlorophenyl)-hydroxy(4-phenyl-2-thiazolyl)methyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (interm. 71).
  • 40
  • [ 1826-12-6 ]
  • [ 4746-97-8 ]
  • [ 1092533-15-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-phenyl-thiazole With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -70℃; for 1h; Stage #2: cyclohexanedione monoethylene ketal In tetrahydrofuran; n-heptane; ethylbenzene at -70 - -65℃; Stage #3: With sodium hydrogen sulfate; water In tetrahydrofuran; n-heptane; ethylbenzene at 20℃; 328 Example 328; 8-(4-Phenylthiazol-2-yl)-1 ,4-dioxaspiro[4.5]decan-8-ol4.5 g of 4-phenylthiazole were dissolved in 80 ml of anhydrous THF and 18.1 ml of a 2 M solution of lithium diisopropylamide in THF/HEP/ethylbenzene (Aldrich) were added dropwise at -700C. The mixture was stirred at -700C for 60 min, then a solution of 4.4 g of 1 ,4-dioxaspiro[4.5]decan-8-one in 50 ml of anhydrous THF was added dropwise at -65°C to -700C. Subsequently, the mixture was warmed to room temperature, poured onto 120 ml of a saturated aqueous sodium hydrogencarbonate solution and extracted three times with 80 ml each of EA. The combined organic phases were dried over magnesium sulfate and the solvent was removed in vacuo. 7.1 g of the title compound were obtained as a pale yellow oil. MS (ESI+): 318
  • 41
  • [ 57516-16-2 ]
  • [ 1826-12-6 ]
YieldReaction ConditionsOperation in experiment
95% With sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; palladium diacetate; triphenylphosphine In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;
95% With sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; palladium diacetate; triphenylphosphine In tetrahydrofuran at 25℃; for 3h; Inert atmosphere; General procedure for the hydrodehalogenation of halogenated heterocycles General procedure: Pd(OAc)2-PPh3, Pd2(dba)3-tbpf, Pd2(dba)3-DavePhos Pd2(dba)3-P(t-Bu)3 Pd2(dba)3-XantPhos and Pd(OAc)2-XPhos. Anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes, then Pd(OAc)2 (7.2 mg, 0.033 mmol, 5 mol%) and PPh3 (17.7 mg, 1.132 mmol, 20 mol%) were added and the resulting mixture stirred at room temperature for 30 min. The halogenated heterocycle (0.66 mmol), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature or heated at 65 °C under argon for the proper time. The residue was taken up in brine and extracted with ethyl acetate. The organic phase was separated, dried, the solvent was evaporated and the residue was purified by flash chromatography (mixtures of petroleum ether and ethyl acetate) to give pure hydrodehalogenated heterocycles
Multi-step reaction with 3 steps 1: N-chloro-succinimide / acetonitrile / 31 h / 20 °C / Inert atmosphere; Reflux 2: palladium diacetate; triphenylphosphine; N,N,N,N,-tetramethylethylenediamine; sodium tetrahydroborate / tetrahydrofuran / 9 h / 20 °C / Inert atmosphere 3: N,N,N,N,-tetramethylethylenediamine; sodium tetrahydroborate; PdCl2(1,1′-bis(di-tertbutylphosphino)ferrocene) / tetrahydrofuran / 20 h / 65 °C / Inert atmosphere
  • 42
  • [ 1403935-14-7 ]
  • [ 1826-12-6 ]
YieldReaction ConditionsOperation in experiment
95% With sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; PdCl2(1,1′-bis(di-tertbutylphosphino)ferrocene) In tetrahydrofuran at 65℃; for 20h; Inert atmosphere;
95% With sodium tetrahydroborate; dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 65℃; for 20h; Inert atmosphere; General procedure for the hydrodehalogenation of halogenated heterocycles General procedure: PdCl2(dppf), PdCl2(tbpf) and (A.caPhos)PdCl2. A mixture of the halogenated heterocycle (0.66 mmol) in anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes. Then, PdCl2(dppf) (27.0 mg, 0.033 mmol, 5.0 mol%), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature under argon for the proper time and then worked up as described above.
  • 43
  • [ 1826-23-9 ]
  • [ 1826-12-6 ]
YieldReaction ConditionsOperation in experiment
93% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 25℃; for 20h; Inert atmosphere; General procedure for the hydrodehalogenation of halogenated heterocycles General procedure: PdCl2(dppf), PdCl2(tbpf) and (A.caPhos)PdCl2. A mixture of the halogenated heterocycle (0.66 mmol) in anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes. Then, PdCl2(dppf) (27.0 mg, 0.033 mmol, 5.0 mol%), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature under argon for the proper time and then worked up as described above.
92% With sodium tetrahydroborate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 20℃; for 22h; Inert atmosphere;
  • 44
  • [ 188585-15-1 ]
  • [ 59278-68-1 ]
  • [ 1826-12-6 ]
YieldReaction ConditionsOperation in experiment
1: 84% 2: 6% With sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; palladium diacetate; triphenylphosphine In tetrahydrofuran at 0℃; for 14h; Inert atmosphere; regioselective reaction;
With sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; palladium diacetate; triphenylphosphine In tetrahydrofuran for 14h; Inert atmosphere; Overall yield = 90 %; regioselective reaction; General procedure for the hydrodehalogenation of halogenated heterocycles General procedure: Pd(OAc)2-PPh3, Pd2(dba)3-tbpf, Pd2(dba)3-DavePhos Pd2(dba)3-P(t-Bu)3 Pd2(dba)3-XantPhos and Pd(OAc)2-XPhos. Anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes, then Pd(OAc)2 (7.2 mg, 0.033 mmol, 5 mol%) and PPh3 (17.7 mg, 1.132 mmol, 20 mol%) were added and the resulting mixture stirred at room temperature for 30 min. The halogenated heterocycle (0.66 mmol), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature or heated at 65 °C under argon for the proper time. The residue was taken up in brine and extracted with ethyl acetate. The organic phase was separated, dried, the solvent was evaporated and the residue was purified by flash chromatography (mixtures of petroleum ether and ethyl acetate) to give pure hydrodehalogenated heterocycles
  • 45
  • [ 1403935-16-9 ]
  • [ 1826-12-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; triphenylphosphine; N,N,N,N,-tetramethylethylenediamine; sodium tetrahydroborate / tetrahydrofuran / 9 h / 20 °C / Inert atmosphere 2: N,N,N,N,-tetramethylethylenediamine; sodium tetrahydroborate; PdCl2(1,1′-bis(di-tertbutylphosphino)ferrocene) / tetrahydrofuran / 20 h / 65 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; palladium diacetate; triphenylphosphine / tetrahydrofuran / 9 h / 25 °C / Inert atmosphere 2: sodium tetrahydroborate; dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 20 h / 65 °C / Inert atmosphere
  • 46
  • [ 98-86-2 ]
  • [ 1826-12-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: phenyltrimethylammonium tribromide / 1,3,5-trimethyl-benzene / 20 °C 2.1: ethanol / Reflux 3.1: sulfuric acid; trifluoroacetic acid; sodium nitrite / water / -15 °C 3.2: -15 - 20 °C
  • 47
  • [ 70-11-1 ]
  • [ 1826-12-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: ethanol / Reflux 2.1: sulfuric acid; trifluoroacetic acid; sodium nitrite / water / -15 °C 2.2: -15 - 20 °C
  • 48
  • [ 1826-12-6 ]
  • [ 2635-13-4 ]
  • C16H11NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With bis(tri-tert-butylphosphine)palladium(0); lithium tert-butoxide In 1,4-dioxane at 80℃; for 48h; regioselective reaction;
  • 49
  • [ 1826-12-6 ]
  • [ 5111-65-9 ]
  • C20H15NOS [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With bis(tri-tert-butylphosphine)palladium(0); lithium tert-butoxide In 1,4-dioxane at 100℃; for 48h; regioselective reaction;
  • 50
  • [ 1826-12-6 ]
  • [ 108-86-1 ]
  • [ 1826-14-8 ]
YieldReaction ConditionsOperation in experiment
77% With bis(tri-tert-butylphosphine)palladium(0); lithium tert-butoxide In 1,4-dioxane at 80℃; for 48h; regioselective reaction;
  • 51
  • [ 1826-12-6 ]
  • [ 556-96-7 ]
  • C17H15NS [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With bis(tri-tert-butylphosphine)palladium(0); lithium tert-butoxide In 1,4-dioxane at 100℃; for 48h; regioselective reaction;
  • 52
  • [ 1826-12-6 ]
  • [ 591-50-4 ]
  • [ 1826-15-9 ]
YieldReaction ConditionsOperation in experiment
77% With tert-Amyl alcohol; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; palladium diacetate; caesium carbonate at 80℃; for 36h; regioselective reaction;
  • 53
  • [ 1826-12-6 ]
  • [ 624-31-7 ]
  • [ 1384515-66-5 ]
YieldReaction ConditionsOperation in experiment
69% With tert-Amyl alcohol; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; palladium diacetate; caesium carbonate at 80℃; for 36h; regioselective reaction;
  • 54
  • [ 1826-12-6 ]
  • [ 624-31-7 ]
  • C24H19NOS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; caesium carbonate; tert-Amyl alcohol; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt / 36 h / 80 °C 2: silver carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triphenylphosphine / water / 24 h / 100 °C
  • 55
  • [ 1826-12-6 ]
  • [ 696-62-8 ]
  • [ 1384515-65-4 ]
YieldReaction ConditionsOperation in experiment
75% With tert-Amyl alcohol; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; palladium diacetate; caesium carbonate at 80℃; for 36h; regioselective reaction;
  • 56
  • [ 1826-12-6 ]
  • [ 2675-79-8 ]
  • [ 1384515-68-7 ]
YieldReaction ConditionsOperation in experiment
60% With tert-Amyl alcohol; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; palladium diacetate; caesium carbonate at 100℃; for 18h; regioselective reaction;
  • 57
  • [ 1826-12-6 ]
  • [ 637-87-6 ]
  • C15H10ClNS [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With tert-Amyl alcohol; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; palladium diacetate; caesium carbonate at 80℃; for 36h; regioselective reaction;
  • 58
  • [ 1826-12-6 ]
  • [ 455-13-0 ]
  • C16H10F3NS [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With tert-Amyl alcohol; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; palladium diacetate; caesium carbonate at 80℃; for 36h; regioselective reaction;
  • 59
  • [ 1826-12-6 ]
  • [ 619-44-3 ]
  • C17H13NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With tert-Amyl alcohol; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; palladium diacetate; caesium carbonate at 100℃; for 18h; regioselective reaction;
  • 60
  • [ 765-58-2 ]
  • [ 1826-12-6 ]
  • C14H11NS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With bis(tri-tert-butylphosphine)palladium(0); lithium tert-butoxide In 1,4-dioxane at 80℃; for 48h; regioselective reaction;
  • 61
  • C22H17NOS [ No CAS ]
  • [ 1826-12-6 ]
YieldReaction ConditionsOperation in experiment
95% With caesium carbonate In m-xylene at 150℃; for 40h; regioselective reaction;
  • 62
  • [ 1826-12-6 ]
  • [ 2104-11-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; caesium carbonate; tert-Amyl alcohol; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt / 36 h / 80 °C 2: [Pd(1,10-phenanthroline)2](PF6)2; caesium carbonate / N,N-dimethyl acetamide / 40 h / 140 °C
Multi-step reaction with 2 steps 1: lithium tert-butoxide; bis(tri-tert-butylphosphine)palladium(0) / 1,4-dioxane / 48 h / 80 °C 2: silver carbonate; dichloro(2,2'-bipyridine)palladium(II) / 1,4-dioxane / 12 h / 120 °C
  • 63
  • [ 1826-12-6 ]
  • C22H17NS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium tert-butoxide; bis(tri-tert-butylphosphine)palladium(0) / 1,4-dioxane / 48 h / 80 °C 2: silver carbonate; dichloro(2,2'-bipyridine)palladium(II) / 1,4-dioxane / 12 h / 120 °C
  • 64
  • [ 1826-12-6 ]
  • C22H17NOS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium tert-butoxide; bis(tri-tert-butylphosphine)palladium(0) / 1,4-dioxane / 48 h / 80 °C 2: silver carbonate; dichloro(2,2'-bipyridine)palladium(II) / 1,4-dioxane / 12 h / 120 °C
  • 65
  • [ 1826-12-6 ]
  • C21H14ClNS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium tert-butoxide; bis(tri-tert-butylphosphine)palladium(0) / 1,4-dioxane / 48 h / 80 °C 2: silver carbonate; dichloro(2,2'-bipyridine)palladium(II) / 1,4-dioxane / 22 h / 120 °C
  • 66
  • [ 1826-12-6 ]
  • C23H17NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium tert-butoxide; bis(tri-tert-butylphosphine)palladium(0) / 1,4-dioxane / 48 h / 80 °C 2: silver carbonate; dichloro(2,2'-bipyridine)palladium(II) / 1,4-dioxane / 22 h / 140 °C
  • 67
  • [ 1826-12-6 ]
  • C23H17NOS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium tert-butoxide; bis(tri-tert-butylphosphine)palladium(0) / 1,4-dioxane / 48 h / 80 °C 2: silver carbonate; dichloro(2,2'-bipyridine)palladium(II) / 1,4-dioxane / 22 h / 140 °C
  • 68
  • [ 1826-12-6 ]
  • C20H14N2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium tert-butoxide; bis(tri-tert-butylphosphine)palladium(0) / 1,4-dioxane / 48 h / 80 °C 2: silver carbonate; dichloro(2,2'-bipyridine)palladium(II) / 1,4-dioxane / 22 h / 140 °C
  • 69
  • [ 1826-12-6 ]
  • [ 120332-29-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; caesium carbonate; tert-Amyl alcohol; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt / 36 h / 80 °C 2: [Pd(1,10-phenanthroline)2](PF6)2; caesium carbonate / N,N-dimethyl acetamide / 40 h / 140 °C
  • 70
  • [ 1826-12-6 ]
  • 2-(4-methoxyphenyl)-4,5-diphenylthiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; caesium carbonate; tert-Amyl alcohol; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt / 36 h / 80 °C 2: [Pd(1,10-phenanthroline)2](PF6)2; caesium carbonate / N,N-dimethyl acetamide / 40 h / 140 °C
  • 71
  • [ 1826-12-6 ]
  • C22H15NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; caesium carbonate; tert-Amyl alcohol; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt / 36 h / 80 °C 2: silver carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triphenylphosphine / water / 24 h / 100 °C
  • 72
  • [ 1826-12-6 ]
  • C21H14ClNS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; caesium carbonate; tert-Amyl alcohol; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt / 36 h / 80 °C 2: [Pd(1,10-phenanthroline)2](PF6)2; caesium carbonate / N,N-dimethyl acetamide / 40 h / 140 °C
  • 73
  • [ 1826-12-6 ]
  • C22H14F3NS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; caesium carbonate; tert-Amyl alcohol; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt / 36 h / 80 °C 2: [Pd(1,10-phenanthroline)2](PF6)2; caesium carbonate / N,N-dimethyl acetamide / 40 h / 140 °C
  • 74
  • [ 1826-12-6 ]
  • C23H17NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; caesium carbonate; tert-Amyl alcohol; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt / 36 h / 80 °C 2: silver carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triphenylphosphine / water / 24 h / 100 °C
  • 75
  • [ 1826-12-6 ]
  • [ 70031-89-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; caesium carbonate; tert-Amyl alcohol; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt / 36 h / 80 °C 2: [Pd(1,10-phenanthroline)2](PF6)2; caesium carbonate / N,N-dimethyl acetamide / 40 h / 140 °C
  • 76
  • [ 98-80-6 ]
  • [ 1826-12-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; lithium tetrafluoroborate / N,N-dimethyl acetamide / 48 h / 100 °C 2: caesium carbonate / m-xylene / 40 h / 150 °C
  • 77
  • [ 1826-12-6 ]
  • [ 615-22-5 ]
  • [ 2103-86-8 ]
YieldReaction ConditionsOperation in experiment
36% With carbonylhydridetris(triphenylphosphine)rhodium(I); 1,3-bis(dicyclohexylphosphine)propane In chlorobenzene for 3h; Reflux; Inert atmosphere; 2-(methylthio)-4-phenylthiazole 3a: 1,3-bis(dicyclohexylphosphino)propane (dcypp: 20.0 mol%, 21.9mg) was dissolved in o-dichlorobenzene (1.0 mL) in a two-necked flask equipped under argon atmosphere. Then, RhH(CO)(PPh3)3 (10.0 mol%, 23.0 mg), 4-phenylthiazole 1a (0.25 mmol, 40.3 mg)and 2-methylthiothiazole 5 (0.75 mmol, 78 L) were added to the solution, and the mixture was heated at reflux for 3 h. Then, the solvent was removed under reduced pressure, and the residue was purified byflash columm chromatography on silica gel giving 2-(methylthio)-4-phenylthiazole 3a (38.5 mg, 74%). 3a11
  • 78
  • [ 288-47-1 ]
  • [ 2103-86-8 ]
  • [ 1826-12-6 ]
  • [ 5053-24-7 ]
YieldReaction ConditionsOperation in experiment
1: 31% 2: 12% With carbonylhydridetris(triphenylphosphine)rhodium(I); 1,3-bis(dicyclohexylphosphine)propane In 1,2-dichloro-benzene for 3h; Reflux; Inert atmosphere; 2-(methylthio)-4-phenylthiazole 3a: 1,3-bis(dicyclohexylphosphino)propane (dcypp: 20.0 mol%, 21.9mg) was dissolved in o-dichlorobenzene (1.0 mL) in a two-necked flask equipped under argon atmosphere. Then, RhH(CO)(PPh3)3 (10.0 mol%, 23.0 mg), 4-phenylthiazole 1a (0.25 mmol, 40.3 mg)and 2-methylthiothiazole 5 (0.75 mmol, 78 L) were added to the solution, and the mixture was heated at reflux for 3 h. Then, the solvent was removed under reduced pressure, and the residue was purified byflash columm chromatography on silica gel giving 2-(methylthio)-4-phenylthiazole 3a (38.5 mg, 74%). 3a11
  • 79
  • [ 1826-12-6 ]
  • [ 5053-24-7 ]
  • [ 2103-86-8 ]
  • 2,5-di(methylthio)thiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 74% 2: 10% With carbonylhydridetris(triphenylphosphine)rhodium(I); 1,3-bis(dicyclohexylphosphine)propane In 1,2-dichloro-benzene for 3h; Inert atmosphere; Reflux; 2-(methylthio)-4-phenylthiazole 3a: 1,3-bis(dicyclohexylphosphino)propane (dcypp: 20.0 mol%, 21.9mg) was dissolved in o-dichlorobenzene (1.0 mL) in a two-necked flask equipped under argon atmosphere. Then, RhH(CO)(PPh3)3 (10.0 mol%, 23.0 mg), 4-phenylthiazole 1a (0.25 mmol, 40.3 mg)and 2-methylthiothiazole 5 (0.75 mmol, 78 L) were added to the solution, and the mixture was heated at reflux for 3 h. Then, the solvent was removed under reduced pressure, and the residue was purified byflash columm chromatography on silica gel giving 2-(methylthio)-4-phenylthiazole 3a (38.5 mg, 74%). 3a11
  • 80
  • [ 1826-12-6 ]
  • [ 5053-24-7 ]
  • [ 288-47-1 ]
  • [ 2103-86-8 ]
YieldReaction ConditionsOperation in experiment
With carbonylhydridetris(triphenylphosphine)rhodium(I); 1,3-bis(dicyclohexylphosphine)propane In 1,2-dichloro-benzene for 3h; Reflux; Inert atmosphere; Overall yield = 52 %; 2-(methylthio)-4-phenylthiazole 3a: 1,3-bis(dicyclohexylphosphino)propane (dcypp: 20.0 mol%, 21.9mg) was dissolved in o-dichlorobenzene (1.0 mL) in a two-necked flask equipped under argon atmosphere. Then, RhH(CO)(PPh3)3 (10.0 mol%, 23.0 mg), 4-phenylthiazole 1a (0.25 mmol, 40.3 mg)and 2-methylthiothiazole 5 (0.75 mmol, 78 L) were added to the solution, and the mixture was heated at reflux for 3 h. Then, the solvent was removed under reduced pressure, and the residue was purified byflash columm chromatography on silica gel giving 2-(methylthio)-4-phenylthiazole 3a (38.5 mg, 74%). 3a11
  • 81
  • [ 1826-12-6 ]
  • [ 141-32-2 ]
  • (E)-butyl 3-(4-phenylthiazol-5-yl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With 5-Nitro-1,10-phenanthroline; copper diacetate; palladium diacetate; caesium carbonate; dimethyl sulfoxide In tert-Amyl alcohol at 100℃; for 12h; Inert atmosphere; regioselective reaction;
  • 82
  • [ 1826-12-6 ]
  • [ 591-50-4 ]
  • 4-phenyl-2-phenylselenothiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With selenium; potassium carbonate; copper dichloride In N,N-dimethyl-formamide at 150℃; for 24h; Schlenk technique; Inert atmosphere;
  • 83
  • [ 1826-12-6 ]
  • (2R)-4-(6-iodo-3-oxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)-2-methyl-2-(methylsulfonyl)-N-((2RS)-(tetrahydro-2H-pyran-2-yl)oxy)butanamide [ No CAS ]
  • (2R)-2-methyl-2-(methylsulfonyl)-4-(3-oxo-6-(4-phenylthiazol-2-yl)-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)-N-((tetrahydro-2H-pyran-2-yl)oxy)butanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
2% Stage #1: 4-phenyl-thiazole With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex In tetrahydrofuran at 0℃; for 0.75h; Stage #2: With zinc(II) chloride In tetrahydrofuran at 20℃; for 0.5h; Stage #3: (2R)-4-(6-iodo-3-oxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)-2-methyl-2-(methylsulfonyl)-N-((2RS)-(tetrahydro-2H-pyran-2-yl)oxy)butanamide With trifuran-2-yl-phosphane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 50℃; 20.i. 20.1. (2R)-2-Methyl-2-(methylsulfony)-4-(3-oxo-6-(4-phenylthiazol-2-yl)-1H-pyrrolo{1 , 2-c]imidazol-2(3H)-yl)-N-((tetrahydro-2H-pyran-2-yl)oxy)butanamide: To anice-chilled solution of 4-phenylthiazole (0.077 g; 0.478 mmol) in THF (2 mL) was slowly addeda freshlyprepared solution of TMPMgCI.LiCl (0.8M in THF, 0.7 mL, 0.564 mmol). The mixture wasstirred for 45 min at0°C before ZnCl2 (1M in THF, 0.6 mL, 0.6 mmol) was added. After stirring for another 30 min at rt, thecompound of Preparation D (0.220 g; 0.419 mmol), Pd(dba)2 (0.013 g; 0.023 mmol) and P(o-furyl)3 (0.011 g;0.046 mmol) were added. The reaction was warmed to 50°C. The reaction mixture was partitioned between(EA (20 mL) and water (10 mL). The evaporation residue was purified by CC (EA-Hept gradient) andsubsequently by prep-HPLC (Method 1) to afford the title product (0.005 g, 2% yield) as an amorphous solid.MS1 (ESI, m/z): 559.2 [M+H*] for CasH3oN4OgSz; tr = 0.97 min.
  • 84
  • [ 1826-12-6 ]
  • [ 501-65-5 ]
  • (E)-5-(1,2-diphenylvinyl)-4-phenylthiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With acetic acid; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine In N,N-dimethyl acetamide at 130℃; for 14h; Inert atmosphere; Glovebox; stereoselective reaction;
  • 85
  • [ 34259-99-9 ]
  • [ 98-80-6 ]
  • [ 1826-12-6 ]
  • 86
  • [ 15803-02-8 ]
  • [ 1826-12-6 ]
  • [ 121-46-0 ]
  • 2-(cis-3-(1-methyl-1H-pyrazol-4-yl)bicyclo[2.2.1]hept-5-en-2-yl)-4-phenylthiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With copper(l) iodide; palladium diacetate; caesium carbonate; bis[2-(diphenylphosphino)phenyl] ether In 1,4-dioxane at 130℃; for 16h; Glovebox; Inert atmosphere;
  • 87
  • 3-azido-3-phenylthietane [ No CAS ]
  • [ 1826-12-6 ]
YieldReaction ConditionsOperation in experiment
25% In o-xylene at 160℃; for 24h; Inert atmosphere;
  • 88
  • [ 66982-46-5 ]
  • [ 1826-12-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trimethylsilylazide; iron(III) chloride / dichloromethane / 14 h / 0 - 20 °C / Inert atmosphere 2: o-xylene / 24 h / 160 °C / Inert atmosphere
  • 89
  • [ 108-86-1 ]
  • [ 1826-12-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: 1 h / -78 °C 2.1: trimethylsilylazide; iron(III) chloride / dichloromethane / 14 h / 0 - 20 °C / Inert atmosphere 3.1: o-xylene / 24 h / 160 °C / Inert atmosphere
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