Brønsted Acid Promoted Facile Synthesis of Benzoacridines from Aromatic Aldehydes and N-Phenyl Naphthylamines.
annulation
dehydrogenation
metal-free
nitrogen heterocycles
oxidation
Journal
Chemistry & biodiversity
ISSN: 1612-1880
Titre abrégé: Chem Biodivers
Pays: Switzerland
ID NLM: 101197449
Informations de publication
Date de publication:
Apr 2023
Apr 2023
Historique:
received:
25
01
2023
accepted:
08
03
2023
medline:
28
4
2023
pubmed:
11
3
2023
entrez:
10
3
2023
Statut:
ppublish
Résumé
A facile method for the rapid synthesis of benzoacridines has been described. This protocol promoted by p-toluenesulfonic acid starts from aromatic aldehydes and N-phenyl naphthylamines, affording a variety of benzoacridines in 30-90 % yields under metal-free conditions. The present approach involves a cascade of condensation, Friedel-Crafts alkylation, annulation and dehydroaromatization in one pot.
Identifiants
pubmed: 36896824
doi: 10.1002/cbdv.202300122
doi:
Substances chimiques
Aldehydes
0
Acridines
0
1-Naphthylamine
9753I242R5
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300122Subventions
Organisme : National Natural Science Foundation of China
ID : 22271244
Organisme : National Natural Science Foundation of China
ID : 22201240
Organisme : Hunan Provincial Natural Science Foundation of China
ID : 2020JJ5531
Organisme : Open Research Fund of School of Chemistry and Chemical Engineering
ID : 2022C02
Organisme : The Undergraduate Investigated Study and Innovated Experiment Plan from Ministry of Education of China and the Science and Technology Innovation Program of Hunan Province
ID : 2020RC1009
Informations de copyright
© 2023 Wiley-VHCA AG, Zurich, Switzerland.
Références
A. J. Pickard, F. Liu, T. F. Bartenstein, L. G. Haines, K. E. Levine, G. L. Kucera, U. Bierbach, Chem. Eur. J. 2014, 20, 16174-16187.
K. Torikai, R. Koga, X. H. Liu, K. Umehara, T. Kitano, K. Watanabe, T. Oishi, H. Noguchi, Y. Shimohigashi, Bioorg. Med. Chem. 2017, 25, 5216-5237.
R. Chen, L. N. Huo, Y. Jaiswal, J. Y. Huang, Z. G. Zhong, J. Zhong, L. Williams, X. Xia, Y. Liang, Z. S. Yan, Molecules 2019, 24, 2065.
F. S. Behbahani, J. Tabeshpour, S. Mirzaei, S. Golmakaniyoon, Z. Tayarani-Najaran, A. Ghasemi, R. Ghodsi, Arch. Pharm. 2019, 352, 1800307.
M. Ikbal, B. Saha, S. Barman, S. Atta, D. R. Banerjee, S. K. Ghosh, N. D. P. Singh, Org. Biomol. Chem. 2014, 12, 3459-3469.
C. X. Li, P. P. Sun, L. J. Yan, Y. Pan, C.-H. Cheng, Thin Solid Films 2008, 516, 6186-6190.
J. Piechowska, D. T. Gryko, J. Org. Chem. 2011, 76, 10220-10228.
J. Zhang, Y. L. Chen, X. M. Chen, X. X. Zheng, W. G. Cao, J. Chen, M. Zhang, Tetrahedron 2014, 70, 5820-5827.
A. Goel, V. Kumar, S. P. Singh, A. Sharma, S. Prakash, C. Singh, R. S. Anand, J. Mater. Chem. 2012, 22, 14880-14888.
M. L. Tan, S. Tong, S. K. Hou, J. S. You, M. X. Wang, Org. Lett. 2020, 22, 5417-5422.
M. Yamato, Y. Takeuchi, M. R. Chang, K. Hashigaki, T. Tsuruo, T. Tashiro, S. Tsukagoshi, Chem. Pharm. Bull. 1990, 38, 3048-3052.
R. Koga, T. Oishi, K. Torikai, Synlett 2015, 26, 2801-2805.
G. J. Atwell, B. C. Baguley, G. J. Finlay, G. W. Rewcastle, W. A. Denny, J. Med. Chem. 1986, 29, 1769-1776.
Q. Su, P. Li, M. N. He, Q. L. Wu, L. Ye, Y. Mu, Org. Lett. 2014, 16, 18-21.
T. J. Wang, W. W. Chen, Y. Li, M. H. Xu, Org. Biomol. Chem. 2015, 13, 6580-6586.
I. Szatmári, K. Belasri, M. Heydenreich, A. Koch, E. Kleinpeter, F. Fülöp, ChemistryOpen 2019, 8, 961-971.
X. L. Pang, Z. B. Lou, M. Li, L. R. Wen, C. Chen, Eur. J. Org. Chem. 2015, 2015, 3361-3369.
H. Wu, Z. G. Zhang, N. N. Ma, Q. F. Liu, T. G. Liu, G. S. Zhang, J. Org. Chem. 2018, 83, 12880-12886.
Z. F. Cao, Y. Zhu, X. M. Li, Y. He, J. L. Zhang, L. Xu, Y. Wei, J. Org. Chem. 2020, 85, 10167-10174.
G. C. Senadi, G. K. Dhandabani, W. P. Hu, J. J. Wang, Green Chem. 2016, 18, 6241-6245.
G. K. Dhandabani, M. R. Mutra, J. J. Wang, Chem. Commun. 2019, 55, 7542-7545.
A. Bernthsen, Justus Liebigs Ann. Chem. 1884, 224, 1-56.
F. D. Popp, J. Org. Chem. 1962, 27, 2658-2659.
H. Koshima, K. Kutsunai, Heterocycles 2002, 57, 1299-1302.
J. A. Seijas, M. P. Vázquez-Tato, M. M. Martínez, J. Rodríguez-Parga, Green Chem. 2002, 4, 390-391.
S. Das, A. J. Thakur, Green Chem. Lett. Rev. 2011, 4, 131-135.
S. P. Chen, Y. X. Li, P. H. Ni, H. W. Huang, G. J. Deng, Org. Lett. 2016, 18, 5384-5387.
S. P. Chen, Y. X. Li, P. H. Ni, B. C. Yang, H. W. Huang, G. J. Deng, J. Org. Chem. 2017, 82, 2935-2942.
P. H. Ni, J. Tan, W. Q. Zhao, H. W. Huang, F. H. Xiao, G. J. Deng, Org. Lett. 2019, 21, 3687-3691.
R. Li, S. X. Jiang, H. L. Zheng, H. W. Lei, Z. Huang, S. P. Chen, G. J. Deng, Green Synth. Catal. 2022, 3, 95-101.
P. Y. Jiang, S. P. Chen, H. W. Huang, K. Hu, Y. Xia, G. J. Deng, Green Synth. Catal. 2021, 2, 78-81.
S. P. Chen, Y. Xia, S. K. Jin, H. W. Lei, K. Y. You, G. J. Deng, J. Org. Chem. 2022, 87, 3212-3222.
F. Fang, H. L. Zheng, W. P. Li, G. J. Mao, S. P. Chen, G. J. Deng, Adv. Synth. Catal. 2022, 364, 2190-2196.
F. Fang, H. L. Zheng, G. J. Mao, S. P. Chen, G. J. Deng, J. Org. Chem. 2022, 87, 6052-6063.
P. Y. Jiang, Z. F. Shan, S. P. Chen, Q. Y. Wang, S. X. Jiang, H. L. Zheng, G. J. Deng, Chin. J. Chem. 2022, 40, 365-370.
Z. H. Qu, T. Tian, G. J. Deng, H. W. Huang, Chin. Chem. Lett. 2022, 34, 107565.
I. Iovel, K. Mertins, J. Kischel, A. Zapf, M. Beller, Angew. Chem. Int. Ed. 2005, 44, 3913-3917;
Angew. Chem. 2005, 117, 3981-3985.
M. Rueping, B. J. Nachtsheim, W. Ieawsuwan, Adv. Synth. Catal. 2006, 348, 1033-1037.
M. M. Wang, L. H. Kong, F. Wang, X. W. Li, Adv. Synth. Catal. 2017, 359, 4411-4416.
J. Li, E. Tan, N. Keller, Y. H. Chen, P. M. Zehetmaier, A. C. Jakowetz, T. Bein, P. Knochel, J. Am. Chem. Soc. 2019, 141, 98-103.