IChO-2025_3.5 (40 points)


context: In contrast to these large structures, the smallest structures contain two metals and four ligands and are called lanterns. Lanterns are formed by ligands such as L, which make two parallel N->Pd bonds. Ligand L has two planes of symmetry and can adopt a planar conformation with the angles shown.
requirement: Give the SMILES of compounds H, I, J, K, and ligand L.
reaction_scheme: reactant_smiles: FC1=C(N)C=CC=C1N
conditions: step: 1
solvent: O=C(OC)C#CC(OC)=O
MeOH
product_name: H
product_formula: C10H10FN3O6
reactant_name: H
reactant_formula: C10H10FN3O6
conditions: step: 1
temperature: 250°C
product_name: I
product_formula: C16H11FN2O6
reactant_name: I
reactant_formula: C16H11FN2O6
conditions: step: 1
reagents: CC(C)OC(/N=N/C(OC(C)C)=O)=O
CC(C)CO
PPh3
product_name: J
product_formula: C24H27FN4O8
reactant_name: J
reactant_formula: C24H27FN4O8
conditions: step: 1
reagents: NaOH
product_name: K
reactant_name: K
conditions: step: 1
reagents: ClC(C(Cl)=O)=O
step: 2
reagents: NC1=CN=CC=C1
NEt3
product_name: L
product_description: compound with two 4-pyridyl groups at 180° and 120° angles

Answer:
name: H
smiles: FC1=C(N/C(C(OC)=O)=C/C(OC)=O)C=CC=C1N/C(C(OC)=O)=C/C(OC)=O
alternative_smiles: FC1=C(/N=C(C(OC)=O)\CC(OC)=O)C=CC=C1/N=C(C(OC)=O)\CC(OC)=O
points: 8
grading: partial_credit: condition: Trivial mistakes (e.g., missing hydrogens, minor bond placement).
deduction: -2
notes: Stereochemistry is not required. Alkenes may be drawn as cis or trans. Imine tautomer receives full credit. If the overall formula is incorrect, award at most 6 pt even with trivial mistakes.
name: I
smiles: FC1=C2C(C(O)=CC(C(OC)=O)=N2)=CC3=C1N=C(C(OC)=O)C=C3O
alternative_smiles: FC1=C2C(C(C=C(C(OC)=O)N2)=O)=CC3=C1NC(C(OC)=O)=CC3=O
points: 10
grading: partial_credit: condition: Four-membered ring lactam (matches formula but strained).
deduction: -6
condition: Indole/indolene structure instead of target.
deduction: -6
notes: Pyridone tautomer earns full credit (10 pt). Errors carried forward from H may be allowed, but if the formula does not match, maximum 6 pt.
name: J
smiles: O=C(OC)C1=CC(OCC(C)C)=C2C(C(F)=C(N=C(C(OC)=O)C=C3OCC(C)C)C3=C2)=N1
alternative_smiles: O=C(OC)C(N(CC(C)C)C1C2C=C3C(N(CC(C)C)C(C(OC)=O)CC3=O)=C1F)=CC2=O
points: 6
grading: partial_credit: condition: Some, but not all, sufficiently acidic OH/NH groups undergo Mitsunobu alkylation OR alkylation shown on groups that would normally be unreactive (standard alcohol OH or amine NH).
deduction: -2
condition: OiBu or NiBu groups drawn in product but corresponding starting material was not OH/NH.
deduction: -4
condition: iPr drawn instead of iBu.
deduction: -1
notes: Errors carried forward from I may be allowed. Full credit (6 pt) when all sufficiently acidic OH/NH undergo correct Mitsunobu alkylation.
name: K
smiles: OC(C1=CC(OCC(C)C)=C2C(C(F)=C(N=C(C(O)=O)C=C3OCC(C)C)C3=C2)=N1)=O
points: 6
grading: partial_credit: condition: Ester hydrolysis incomplete or incorrect; other base-labile groups not hydrolyzed.
deduction: -3
notes: Errors carried forward from J may be allowed, but the structure must reflect correct ester hydrolysis; other base-labile functional groups must be hydrolyzed.
name: L
smiles: O=C(NC1=CN=CC=C1)C2=CC(OCC(C)C)=C3C(C(F)=C(N=C(C(NC4=CN=CC=C4)=O)C=C5OCC(C)C)C5=C3)=N2
points: 10
grading: partial_credit: condition: Ligand does not show two planes of symmetry.
deduction: -2
condition: Both outer rigid pieces are not at 180°.
deduction: -2
condition: Central rigid piece is not at 120°.
deduction: -2
condition: Carbons from oxalyl chloride have been incorporated into the final ligand.
deduction: -2
notes: Errors carried forward from K may be allowed, but overall transformation must be feasible under the stated conditions for full credit.