An Easy Access to Furan-Fused Polyheterocyclic Systems
Abstract
:1. Introduction
2. Results
3. Materials and Methods
3.1. General Procedure for the Reactions of Substrates 4 with β-Naphthol
2-(2-(Methylsulfonyl)phenyl)-1-(p-tolyl)-1,2-dihydronaphtho[2,1-b]furan (5a)
2-(2-(Methylsulfonyl)phenyl)-1-(o-tolyl)-1,2-dihydronaphtho[2,1-b]furan (5b)
1-(4-Methoxyphenyl)-2-(2-(methylsulfonyl)phenyl)-1,2-dihydronaphtho[2,1-b]furan (5c)
1-(4-Chlorophenyl)-2-(2-(methylsulfonyl)phenyl)-1,2-dihydronaphtho[2,1-b]furan (5d)
2-(2-(Methylsulfonyl)phenyl)-1-(naphthalen-1-yl)-1,2-dihydronaphtho[2,1-b]furan (5e)
2-(2-(Methylsulfonyl)phenyl)-1-(thiophen-2-yl)-1,2-dihydronaphtho[2,1-b]furan (5f)
3.2. General Procedure for the Oxidative Aromatization Reaction of Dihydronaphthofurans 5a–f to Naphthofurans 6a–f
2-(2-(Methylsulfonyl)phenyl)-1-(p-tolyl)naphtho[2,1-b]furan (6a)
2-(2-(Methylsulfonyl)phenyl)-1-(o-tolyl)naphtho[2,1-b]furan (6b)
1-(4-Methoxyphenyl)-2-(2-(methylsulfonyl)phenyl)naphtho[2,1-b]furan (6c)
1-(4-Chlorophenyl)-2-(2-(methylsulfonyl)phenyl)naphtho[2,1-b]furan (6d)
2-(2-(Methylsulfonyl)phenyl)-1-(naphthalen-1-yl)naphtho[2,1-b]furan (6e)
2-(2-(Methylsulfonyl)phenyl)-1-(thiophen-2-yl)naphtho[2,1-b]furan (6f)
3.3. General Procedure for the Reaction of Substrates 4 with 8-Hydroxyquinoline
2-(2-(Methylsulfonyl)phenyl)-3-(p-tolyl)-2,3-dihydrofuro[3,2-h]quinoline (7a)
2-(2-(Methylsulfonyl)phenyl)-3-(o-tolyl)-2,3-dihydrofuro[3,2-h]quinoline (7b)
2-(2-(Methylsulfonyl)phenyl)-3-(p-anysyl)-2,3-dihydrofuro[3,2-h]quinoline (7c)
3-(4-Chlorophenyl)-2-(2-(methylsulfonyl)phenyl)-2,3-dihydrofuro[3,2-h]quinoline (7d)
3.4. General Procedure for the Oxidative Aromatization Reaction of Dihydrofuroquinolines 7a, d to Furoquinolines 8a, d
2-(2-(Methylsulfonyl)phenyl)-3-(p-tolyl)furo[3,2-h]quinoline (8a)
3-(4-Chlorophenyl)-2-(2-(methylsulfonyl)phenyl)furo[3,2-h]quinoline (8d)
3.5. Procedure for the Reaction of Substrate 4a with 4-Hydroxycoumarin
2-(2-(Methylsulfonyl)phenyl)-3-(p-tolyl)-2,3-dihydro-4H-furo[3,2-c]chromen-4-one (9a)
3.6. General Procedure for the 6π-Electrocyclization of Naphthofurans 6a–f
13-Methylnaphtho[2,1-b]phenanthro[9,10-d]furan (11a)
13-Methoxynaphtho[2,1-b]phenanthro[9,10-d]furan (11c)
13-Chloronaphtho[2,1-b]phenanthro[9,10-d]furan (11d)
Chryseno[6,5-b]naphtho[1,2-d]furan (11e)
Naphtho[2,1-b]thieno[2’,3’:3,4]naphtho[2,1-d]furan (11f)
2-(2-(Methylthio)phenyl)-1-(p-tolyl)-1,2-dihydronaphtho[2,1-b]furan (12a)
2-(2-(Methylthio)phenyl)-1-(p-tolyl)naphtho[2,1-b]furan (13a)
3.7. Crystal Structure of 5a
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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4 | Ar in 4 | 5 (Yields %) a |
---|---|---|
4a | p-MeC6H4 | 5a, 92 |
4b | o-MeC6H4 | 5b, 89 |
4c | p-MeOC6H4 | 5c, 94 |
4d | p-ClC6H4 | 5d, 93 |
4e | 1-Naphthyl | 5e, 87 |
4f | 2-Thienyl | 5f, 96 |
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Benzi, A.; Bianchi, L.; Giorgi, G.; Maccagno, M.; Petrillo, G.; Spinelli, D.; Tavani, C. An Easy Access to Furan-Fused Polyheterocyclic Systems. Molecules 2022, 27, 3147. https://doi.org/10.3390/molecules27103147
Benzi A, Bianchi L, Giorgi G, Maccagno M, Petrillo G, Spinelli D, Tavani C. An Easy Access to Furan-Fused Polyheterocyclic Systems. Molecules. 2022; 27(10):3147. https://doi.org/10.3390/molecules27103147
Chicago/Turabian StyleBenzi, Alice, Lara Bianchi, Gianluca Giorgi, Massimo Maccagno, Giovanni Petrillo, Domenico Spinelli, and Cinzia Tavani. 2022. "An Easy Access to Furan-Fused Polyheterocyclic Systems" Molecules 27, no. 10: 3147. https://doi.org/10.3390/molecules27103147