HCID 19874617, compound → HCID 19874631, compound

HRID 1607424Notes

Reaction equation

HRID 1607424 reaction equation
COCCC(=O)CC1C=C(OC)C=CC=1.COC(OC)CC(=O)CC1C=CC(F)=CC=1.CO[C:34]([C:36]1[O:37][CH:38]=[CH:39][C:40]=1[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:35]>>[O:37]1[CH:38]=[CH:39][C:40]2[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][C:46]=3[C:34](=[O:35])[C:36]1=2.[O:37]1[CH:38]=[CH:39][C:40]2[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[CH2:34][C:36]1=2

Participants

5

Reactant 3

HCID 19874617HCID 19874617, compoundHCID 19874659HCID 19874659, compoundHCID 54104529HCID 54104529, compound

Product 2

HCID 19874631HCID 19874631, compoundHCID 19874669HCID 19874669, compound

Procedure

Synthetic substrates 8H-indeno[2,1-b]furan-8-one and 8H-indeno[2,1-b]furan and their derivatives are prepared in accordance with the following. Substituted and unsubstituted 3-arylfuran-2-carboxylic acids are prepared according to a general procedure of Burgess, J. Org. Chem., 21, 102 (1956), wherein, 4,5-dimethoxy-1-phenyl-2-butanone and related 2' to 4' substituted phenyl analogs (e.g., 4,4-dimethoxy-1-(4'-fluorophenyl)-2-butanone, prepared according to the general procedure of Royals and Brannoch, J. Amer. Chem. Soc., 75, 2050 (1953)) are converted into 3-phenylfuran-2-carboxylic acid methyl ester (e.g., 3'-(4'-fluorophenylfuran-2-carboxylic acid methyl ester) by the Darzens glycidic ester condensation (Darzens, Compt. Rend., 139, 1214 (1904)). This rearrangement of the glycidic ester yields the furoic ester. The furoic ester can be hydrolyzed in alkaline methanolic solution to yield, for example, 3-(4'-fluorophenyl)-furan-2-carboxylic acid. The furoic acid product can be cyclized via the aroyl chloride in the presence of stannic chloride or aluminum chloride to yield the ketone, e.g., 6-fluoro-8H-indeno [2,1-b]furan-8-one. This ketone can be derivatized in accordance with Method V. Hydantoin derivatization (Method I) yields the spiro-hydantoin, e.g., spiro-(6-fluoro-8H-indeno[2,1-b]furan-8,4'-imidazolidine)-2',5'-dione. Reduction according to methods cited in Method VIII yields the corresponding 8H-indeno[2,1-b]furan derivative which can be derivatized in accordance with Methods II, III and IV into the corresponding spiro-thiazolidinedione, spiro-oxazolidinedione and spiro-succinimide. Furthermore, the spiro-derivatives may be further derivatized according to Method VI.

Workup

  1. customSubstituted and unsubstituted 3-arylfuran-2-carboxylic acids are prepared
  2. customprepared

Sources & evidence

ORD record
ord-511855cc453b4438a52ca8410a59a544
Source dataset
uspto-grants-1989_09
Patent number
US04864028

Reaction notes

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