US10385035B2ActiveUtilityA1
Dinaphthothiophene compounds
Est. expiryJun 20, 2037(~10.9 yrs left)· nominal 20-yr term from priority
C07D 333/74C07D 333/50
45
PatentIndex Score
0
Cited by
45
References
22
Claims
Abstract
The present invention generally relates to various dinaphthothiophene compounds and processes for preparing these compounds.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1. A dinaphthothiophene compound of Formula III:
wherein R 3 is hydroxy, substituted C 1 -C 20 alkyl, or substituted or unsubstituted aryl; R 4 is hydrogen, hydroxy, substituted or unsubstituted C 1 -C 20 alkyl, or substituted or unsubstituted aryl; and n is 1 or 2.
2. The compound of claim 1 wherein R 3 is hydroxy, C 1 -C 20 alkoxy, C 1 -C 20 haloalkyl, C 1 -C 20 haloalkoxy, aryl, alkyl-substituted aryl, halo-substituted aryl, or hydroxy-substituted aryl.
3. The compound of claim 1 wherein R 3 is hydroxy, C 1 -C 10 alkoxy, C 1 -C 10 haloalkyl, C 1 -C 10 haloalkoxy, aryl, alkyl-substituted aryl, halo-substituted aryl, or hydroxy-substituted aryl.
4. The compound of claim 1 wherein R 3 is hydroxy, methoxy, ethoxy, propoxy, trifluoromethyl, phenyl, hydroxyphenyl, ethylphenyl, carboxyphenyl, naphthyl, anthracenyl, biphenyl, tolyl, cumyl, styryl, ortho-xylyl, meta-xylyl, para-xylyl, fluorophenyl, chlorophenyl, bromobenzyl, or iodobenzyl.
5. The compound of claim 1 wherein R 4 is hydrogen, hydroxy, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, C 1 -C 20 haloalkyl, C 1 -C 20 haloalkoxy, aryl, alkyl-substituted aryl, halo-substituted aryl, or hydroxy-substituted aryl.
6. The compound of claim 1 wherein R 4 is hydrogen, hydroxy, C 1 -C 10 alkyl, C 1 -C 10 alkoxy, C 1 -C 10 haloalkyl, C 1 -C 10 haloalkoxy, aryl, alkyl-substituted aryl, halo-substituted aryl, or hydroxy-substituted aryl.
7. The compound of claim 1 wherein R 4 is hydrogen, hydroxy, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, trifluoromethyl, phenyl, hydroxyphenyl, ethylphenyl, carboxyphenyl, naphthyl, anthracenyl, biphenyl, tolyl, cumyl, styryl, ortho-xylyl, meta-xylyl, para-xylyl, fluorophenyl, chlorophenyl, bromobenzyl, or iodobenzyl.
8. A dinaphthothiophene compound of Formula III:
wherein R 3 is hydroxy, C 1 -C 20 alkoxy, C 1 -C 20 haloalkyl, C 1 -C 20 haloalkoxy, aryl, alkyl-substituted aryl, halo-substituted aryl, or hydroxy-substituted aryl; R 4 is hydrogen, hydroxy, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, C 1 -C 20 haloalkyl, C 1 -C 20 haloalkoxy, aryl, alkyl-substituted aryl, halo-substituted aryl, or hydroxy-substituted aryl; and n is 1 or 2.
9. The compound of claim 8 wherein R 3 is hydroxy, methoxy, ethoxy, propoxy, trifluoromethyl, phenyl, hydroxyphenyl, ethylphenyl, carboxyphenyl, naphthyl, anthracenyl, biphenyl, tolyl, cumyl, styryl, ortho-xylyl, meta-xylyl, para-xylyl, fluorophenyl, chlorophenyl, bromobenzyl, or iodobenzyl and R 4 is hydrogen, hydroxy, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, trifluoromethyl, phenyl, hydroxyphenyl, ethylphenyl, carboxyphenyl, naphthyl, anthracenyl, biphenyl, tolyl, cumyl, styryl, ortho-xylyl, meta-xylyl, para-xylyl, fluorophenyl, chlorophenyl, bromobenzyl, or iodobenzyl.
10. A dinaphthothiophene compound of Formula III:
wherein R 3 is hydrogen, hydroxy, substituted or unsubstituted C 1 -C 20 alkyl, or substituted or unsubstituted aryl; R 4 is hydrogen, hydroxy, substituted or unsubstituted C 1 -C 20 alkyl, or substituted or unsubstituted aryl; and n is 1 or 2, and wherein R 3 and R 4 are different.
11. The compound of claim 10 wherein R 3 is hydrogen, hydroxy, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, C 1 -C 20 haloalkyl, C 1 -C 20 haloalkoxy, aryl, alkyl-substituted aryl, halo-substituted aryl, or hydroxy-substituted aryl.
12. The compound of claim 10 wherein R 3 is hydrogen, hydroxy, C 1 -C 10 alkyl, C 1 -C 10 alkoxy, C 1 -C 10 haloalkyl, C 1 -C 10 haloalkoxy, aryl, alkyl-substituted aryl, halo-substituted aryl, or hydroxy-substituted aryl.
13. The compound of claim 10 wherein R 3 is hydrogen, hydroxy, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, trifluoromethyl, phenyl, hydroxyphenyl, ethylphenyl, carboxyphenyl, naphthyl, anthracenyl, biphenyl, tolyl, cumyl, styryl, ortho-xylyl, meta-xylyl, para-xylyl, fluorophenyl, chlorophenyl, bromobenzyl, or iodobenzyl.
14. The compound of claim 10 wherein R 4 is hydrogen, hydroxy, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, C 1 -C 20 haloalkyl, C 1 -C 20 haloalkoxy, aryl, alkyl-substituted aryl, halo-substituted aryl, or hydroxy-substituted aryl.
15. The compound of claim 10 wherein R 4 is hydrogen, hydroxy, C 1 -C 10 alkyl, C 1 -C 10 alkoxy, C 1 -C 10 haloalkyl, C 1 -C 10 haloalkoxy, aryl, alkyl-substituted aryl, halo-substituted aryl, or hydroxy-substituted aryl.
16. The compound of claim 10 wherein R 4 is hydrogen, hydroxy, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, trifluoromethyl, phenyl, hydroxyphenyl, ethylphenyl, carboxyphenyl, naphthyl, anthracenyl, biphenyl, tolyl, cumyl, styryl, ortho-xylyl, meta-xylyl, para-xylyl, fluorophenyl, chlorophenyl, bromobenzyl, or iodobenzyl.
17. The compound of claim 10 wherein R 3 is methoxy, ethoxy, propoxy, or trifluoromethyl and R 4 is hydrogen, methyl, ethyl, propyl, butyl, or trifluoromethyl.
18. A dinaphthothiophene compound of Formula III:
wherein R 3 is hydrogen, hydroxy, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, C 1 -C 20 haloalkyl, C 1 -C 20 haloalkoxy, aryl, alkyl-substituted aryl, halo-substituted aryl, or hydroxy-substituted aryl; R 4 is hydrogen, hydroxy, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, C 1 -C 20 haloalkyl, C 1 -C 20 haloalkoxy, aryl, alkyl-substituted aryl, halo-substituted aryl, or hydroxy-substituted aryl; and n is 1 or 2, and wherein R 3 and R 4 are different.
19. A process for preparing the dinaphthothiophene compound of claim 1 , comprising oxidizing a dinaphthothiophene compound of Formula III-A:
to form the dinaphthothiophene compound of Formula III, wherein R 3 and R 4 are as defined for Formula III.
20. The process of claim 19 further comprising:
formylating 3,4-dibromothiophene to form 4-bromothiophene-3-carbaldehyde;
reacting, in the presence of a catalyst comprising palladium, a base, and organic solvent, 4-bromothiophene-3-carbaldehyde with a phenylethenyl boronic compound of Formula C-1:
to form a 3-formyl-4-styrylthiophene compound of Formula C-2:
reacting, in the presence of sodium hydride, the 3-formyl-4-styrylthiophene compound of Formula C-2 with a 4-substituted phosphonic acid diethyl ester compound of Formula C-3:
to form a compound of Formula C-4:
irradiating the compound of Formula C-4 with UV light in the presence of iodine and propylene oxide to form the dinaphthothiophene compound of Formula III-A:
wherein R 3 and R 4 are as defined for Formula III.
21. A process for preparing the dinaphthothiophene compound of claim 10 , comprising oxidizing a dinaphthothiophene compound of Formula III-A:
to form the dinaphthothiophene compound of Formula III, wherein R 3 and R 4 are as defined for Formula III.
22. The process of claim 21 further comprising:
formylating 3,4-dibromothiophene to form 4-bromothiophene-3-carbaldehyde;
reacting, in the presence of a catalyst comprising palladium, a base, and organic solvent, 4-bromothiophene-3-carbaldehyde with a phenylethenyl boronic compound of Formula C-1:
to form a 3-formyl-4-styrylthiophene compound of Formula C-2:
reacting, in the presence of sodium hydride, the 3-formyl-4-styrylthiophene compound of Formula C-2 with a 4-substituted phosphonic acid diethyl ester compound of Formula C-3:
to form a compound of Formula C-4:
irradiating the compound of Formula C-4 with UV light in the presence of iodine and propylene oxide to form the dinaphthothiophene compound of Formula III-A:
wherein R 3 and R 4 are as defined for Formula III.Join the waitlist — get patent alerts
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