- Synthesis of Acridines from o-Aminoaryl Ketones and Arylboronic Acids by Copper Trifluoroacetate-Mediated Relay Reactions
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An efficient and practical method for the synthesis of medicinally important acridines from readily available o-aminoaryl ketones and arylboronic acids was developed using copper(II)-mediated relay reactions that involve intermolecular Chan-Lam cross-coupling and subsequent intramolecular Friedel-Crafts-type reactions. A sole promoter, i.e., Cu(OTf)2, was used; therefore, strongly acidic and basic conditions, nonreadily available or expensive substrates, additives, and noble-metal catalysts were not needed.
- Wu, Hao,Zhang, Zhiguo,Ma, Nana,Liu, Qingfeng,Liu, Tongxin,Zhang, Guisheng
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p. 12880 - 12886
(2018/10/09)
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- Tandem arylation/friedel-crafts reactions of o-acylanilines with diaryliodonium salts: A modular synthesis of acridine derivatives
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A modular method to synthesize acridine derivatives was developed with o-acylanilines and diaryliodonium salts. The reactions proceeded smoothly under Cu-catalyzed or metal-free reaction conditions at elevated temperature through tandem arylation/Friedel-Crafts reactions.
- Pang, Xinlong,Lou, Zhenbang,Li, Ming,Wen, Lirong,Chen, Chao
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supporting information
p. 3361 - 3369
(2015/05/20)
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- Rapid synthesis of acridines using microwave
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Microwave irradiation for several minutes caused reaction of diarylamines with carboxylic acids in the presence of zinc chloride to give 9-substituted acridines in good yield.
- Koshima, Hideko,Kutsunai, Kosuke
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p. 1299 - 1302
(2007/10/03)
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- Synthesis of the Non-K-Region Dihydrodiols of 7-Methylbenzacridine
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The synthesis of the four non-K-region trans-dihydrodiols of 7-methylbenzacridine (2) are described.The trans-8,9- and -10,11-dihydrodiols 13 and 16 were prepared from 7-methyl-8,9,10,11-tetrahydrobenzacridine (3) via the trans-8,9-diacetoxy-7-methyl-8,9,10,11-tetrahydrobenzacridine (10) and its 10,11-isomer (14) by selective benzylic bromination followed by dehydrobromination.The trans-tetrahydro diacetates were obtained through the alkenes 6 and 7 and their epoxide derivatives. trans-1,2- and -3,4-dihydrodiols 22 and 24 were similarly prepared from the trans-1,2- and -3,4-diacetates of 7-methyl-1,2,3,4-tetrahydrobenzacridine (19 and 20).The latter were products of the Prevost reaction on mixed 3,4- and 1,2-dihydro-7-methylbenzacridines (17 and 18).
- Duke, Colin C.,Murphy, Peter T.,Holder, Gerald M.
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p. 4446 - 4451
(2007/10/02)
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