Cyclization of 1-acylaminoacridones into 7H-pyrido[2,3,4-kl]acridin-2(3H)-ones

Gorelik, M. V.; Titova, S. P.; Gordievskaya, E. V.

doi:10.1007/s11172-006-0444-3

Cited by 4 publications

(4 citation statements)

References 10 publications

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“…Intramolecular cyclization of 1‐( N ‐acylamino)acridones 65 forming pyridoacridones 66 was achieved in basic conditions . Only secondary amides 65 (R = H) containing an activating substituent (X = CN, CO 2 Et) in the acyl group cyclize with potassium hydroxide in DMF to pyridoacridones 66 (X = CN, CO 2 Et).…”

Section: Pyrido[234‐kl]acridinementioning

confidence: 99%

“…[38] Intramolecular cyclization of 1-(N-acylamino)acridones 65 forming pyridoacridones 66 was achieved in basic conditions. [39] Only secondary amides 65 (R = H) containing an activating substituent (X = CN, CO 2 Et) in the acyl group cyclize with potassium hydroxide in DMF to pyridoacridones 66 (X = CN, CO 2 Et). However, tertiary amides 65 (R = alkyl) underwent cyclization in the same conditions even without an activating substituent in the acyl group (Scheme 20).…”

Section: Tetracyclic Systemsmentioning

confidence: 99%

“…Cyclization of N-acylaminoacridones 66. [39] Treatment of aminoacridone 67 with phosphorus pentachloride in benzene and then with a malonic acid derivative, in the presence of a base, directly gave pyrido[2,3,4-kl]acridine derivatives 68 and 69. With ethyl cyanoacetate as active compound acridine 68 (X = CN) and acridin-2-one 69 (X = CN) were obtained in a ratio ca.…”

Section: Tetracyclic Systemsmentioning

confidence: 99%

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Pyridoacridines in the 21st Century

Joule

Álvarez

2019

Eur J Org Chem

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This minireview summarizes the work developed during this century with compounds containing the pyridoacridine scaffold in its different isomeric forms. The isolation of natural products, syntheses, bioactivities, chelation capacity, and other properties of compounds containing this framework are discussed. For reasons of length, only compounds containing a maximum of seven condensed rings have been considered, with a few exceptions.

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Section: Pyrido[234‐kl]acridinementioning

confidence: 99%

Section: Tetracyclic Systemsmentioning

confidence: 99%

Section: Tetracyclic Systemsmentioning

confidence: 99%

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Pyridoacridines in the 21st Century

Joule

Álvarez

2019

Eur J Org Chem

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“…1 A reaction of 9 chloro 1 nitroacridine (5) with malononitrile in the presence of KOH in DMSO afforded 9 dicyanomethylidene 1 nitro 9,10 dihydroacridine (6) in high yield (Scheme 2). Pyridoacridines 3a,b were identical with compounds obtained by acylation of 1 amino 10 methyl acridone with ethyl cyanoacetate and ethyl malonate, re spectively, followed by base catalyzed cyclization.…”

mentioning

confidence: 99%

Syntheses of 7H-pyrido-and 7H-pyrano[2,3,4-kl]acridin-2(3H)-ones from 9-chloroacridines

2006

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A method for peri annulation of the pyridine or pyran ring to acridine was developed and used to obtain 7H pyrido and 7H pyrano[2,3,4 kl]acridin 2(3H) ones. The peri groups were formed by a reaction of 9 chloro 1 nitroacridine with a CH acid (malononitrile, ethyl cyanoacetate, and ethyl malonate) followed by reduction of the nitro group, or by a reaction of 1 amino 10 methylacridone with PCl 5 and then with a CH acid. Replacement of the chlorine atom in 9 chloro 1 methoxyacridines by the residue of the CH acid with subsequent heating in an acidic medium afforded 7H pyrano[2,3,4 kl]acridin 2(3H) ones, which belong to a novel heterocyclic system.

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