Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[O:13][C:12](=[CH:14][N+:15]([O-:17])=[O:16])[NH:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[CH3:18][N:19]([CH2:21][C:22]1[S:26][C:25]([CH2:27][SH:28])=[CH:24][C:23]=1[CH3:29])[CH3:20].[CH2:30]1[NH:32][CH2:31]1>C(Cl)Cl.CO>[CH3:20][N:19]([CH2:21][C:22]1[S:26][C:25]([CH2:27][S:28][CH2:30][CH2:31][NH:32][C:12]([NH:11][CH2:10][CH:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[OH:13])=[CH:14][N+:15]([O-:17])=[O:16])=[CH:24][C:23]=1[CH3:29])[CH3:18]
Reactant: C1CN1
Reactant: Cc1cc(CS)sc1CN(C)C
Reactant: COc1cccc(C2CNC(=C[N+](=O)[O-])O2)c1
Solvent: ClCCl
Solvent: CO
Product: COc1cccc(C(O)CNC(=C[N+](=O)[O-])NCCSCc2cc(C)c(CN(C)C)s2)c1
Reaction time: 5 h
Yield: 83.8 %

Procedure:
In a mixed solvent of 20 ml of methylene chloride and 10 ml of methanol was dissolved 2.4 g of 5-(3-methoxyphenyl)-2-nitromethyleneoxazolidine at room temperature, and a solution of 2.0 g of 5-(dimethylamino) methyl-2-mercaptomethyl-4-methylthiophene in 5 ml of methanol was added thereto in a nitrogen atmosphere. Then, the solution of 0.5 g of ethyleneimine in 5 ml of methanol was added dropwise at the same temperature over a period of 10 minutes. After addition, the resulting solution was subjected to reaction with stirring for 5 hours. After the completion of the reaction, the solvent was removed by distillation under reduced pressure, and the residue obtained was purified by a column chromatography (Wako Silica Gel C-200, eluent; chloroform: ethanol=30:1 by volume) to obtain 4.0 g (yield 83.5%) of oily N-{2-[[5-(dimethylamino)methyl-4-methyl-2-thienyl]methylthio]ethyl}-N'-[2-(3-methoxyphenyl)-2-hydroxyethyl]-2-nitro-1,1-ethenediamine.
Reaction SMILES: OO.[Ce:3].[NH2:4][C@H:5]([C:9]([OH:11])=[O:10])[C@@H:6]([CH3:8])[OH:7]>>[NH2:4][CH:5]([C:9]([OH:11])=[O:10])[CH:6]([CH3:8])[OH:7].[Ce:3]
Reactant: C[C@@H](O)[C@H](N)C(=O)O
Agent: OO
Agent: [Ce]
Product: CC(O)C(N)C(=O)O
Temperature: 40 °C

Procedure:
Into a 600 ml glass beaker containing a magnetic stir bar was introduced 500 ml of high purity (HP) water. A 2.194 gm quantity of DL-threonine was dissolved in this volume. A 10.0 gm quantity of Ce(NO3)3·6(H2O) was added, thereby forming a molar ratio of L-threonine to cerium ion of 0.8. Then a 10 ml solution containing 2.40 gm of 50% H2O2 (1.5 molar ratio of H2O2 to cerium ion) was added slowly to the cerium and threonine solution mixture. The pH was further adjusted to about 4.3. The reaction product was then heated to 40° C. for 1 hour. The product suspension was then washed to remove salts by diafiltration, during which about two turnover volumes of HP water were added, and then concentrated to a final ionic conductivity of about 3.05 mS/cm and a pH of 3.1.
Reaction SMILES: [CH3:1][C:2]1([CH3:19])[CH2:7][CH:6]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[O:3]1.F[B-](F)(F)F.[O:25]=[N+:26]=[O:27]>C(#N)C>[CH3:1][C:2]1([CH3:19])[CH2:7][CH:6]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:15]=[C:16]([N+:26]([O-:27])=[O:25])[CH:17]=[CH:18][C:4]=2[O:3]1
Reactant: O=[N+]=O
Reactant: Cc1cccnc1C1CC(C)(C)Oc2ccccc21
Agent: F[B-](F)(F)F
Solvent: CC#N
Product: Cc1cccnc1C1CC(C)(C)Oc2ccc([N+](=O)[O-])cc21
Yield: 46.4 %

Procedure:
685 mg of 3,4-dihydro-2,2-dimethyl-4-(3-methyl-2-pyridyl)-2H-1-benzopyran were dissolved in 20 ml of acetonitrile at room temperature and 360 mg of nitronium tetrafluoroborate were added. After 30 minutes the solvent was removed by evaporation and ethyl acetate and water were added. The organic phase was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:4) for the elution. There were obtained 374 mg of 3,4-dihydro-2,2-dimethyl-4-(3-methyl-2-pyridyl) -6-nitro-2H-1-benzopyran in the form of a solid of melting pOint 164-165° C. after recrystallization from t-butyl methyl ether.